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The Berkshires, Season by Season

Written by Red Cottage on . Posted in Upstate Field Guide, Blog, Local Activity Guide, Seasonal + Events.

Most people think of the Berkshires as a summer destination. And summer is wonderful. But the region earns its keep across all four seasons in ways that surprise even repeat visitors. The museums are quieter in spring. The estates are at their most dramatic in fall. Winter brings a stillness to these hills that is genuinely hard to find anywhere else in the Northeast.

Red Cottage has spent nearly two decades learning this region at every season. What follows is our guide to the Berkshires as we know it: honest, unhurried, and written for travelers who prefer depth over convenience.

Summer: June through August

Summer is the Berkshires at full volume. The performance venues open, the gardens peak, and the region fills with visitors who have been coming back for decades. If this is your first trip, summer is the right introduction.

Tanglewood, Lenox

Tanglewood is the summer home of the Boston Symphony Orchestra, and the lawn at night is one of the great traditions of American summer. People bring picnic blankets, cheese boards, and wine, and the music drifts out across the field as the sun goes down. A lawn ticket runs around $30 to $40, one of the best cultural deals in the Northeast. Book early. Popular weekends sell out months ahead.

  • Rating: 4.8 stars (1,795 reviews)
  • Address: 297 West St, Lenox, MA 01240
  • Season: Late June through early September Bring: Blanket, low chairs, a proper picnic, layers for the evening

Learn more about Tanglewood

Jacob’s Pillow Dance Festival, Becket

The longest-running international dance festival in the United States. More than 50 companies pass through each summer, from major ballet troupes to experimental modern groups. The outdoor stage with the mountain backdrop is unforgettable, and free performances on the Inside/Out stage happen throughout the season. Check the calendar before you go.

  • Rating: 4.5 stars (112 reviews)
  • Address: 358 George Carter Rd, Becket, MA 01223
  • Season: Mid-June through late August Good to know: Free Fridays and pay-what-you-want shows run regularly.

Learn more about Jacob’s Pillow Dance Festival

MASS MoCA, North Adams

The summer crowds are thinner than you might expect inside the galleries, and the campus cafe makes a good lunch stop between the indoor and outdoor installations. Wall drawings by Sol LeWitt take up entire floors. James Turrell installations swallow you whole. Plan two to three hours and save energy for the upper galleries.

  • Rating: 4.7 stars (4,459 reviews)
  • Address: 1040 MASS MoCA Way, North Adams, MA 01247
  • Hours: Daily 10 AM to 5 PM, closed Tuesdays

Learn more about MASS MoCA

The Clark Art Institute, Williamstown

Over 30 Renoirs, plus Monet, Degas, and Pissarro, in what we consider the most beautifully placed museum in the Northeast. After the galleries, walk the trails behind the building. The reflecting pool at sunset is worth staying for.

  • Rating: 4.9 stars (621 reviews)
  • Address: 225 South St, Williamstown, MA 01267
  • Hours: 10 AM to 5 PM, closed Mondays

Learn more about The Clark Art Institute

Fall: September through October

Fall in the Berkshires is not subtle. The hills go gold and red from the second week of October, the air sharpens, and the summer crowds thin out almost immediately after Labor Day. This is when the region shows its best face to the people patient enough to wait for it.

Chesterwood, Stockbridge

Chesterwood was the summer studio of Daniel Chester French, the sculptor behind the seated Lincoln at the Lincoln Memorial. The woodland sculpture trails that wind through the property are at their most beautiful in October, when the canopy turns and the light filters through in a way that makes the outdoor works look completely different than they do in any other season.

  • Rating: 4.7 stars (224 reviews)
  • Address: 4 Williamsville Rd, Stockbridge, MA 01262
  • Season: Friday through Sunday, 11 AM to 4 PM in season Insider tip: Book a guided tour, the context makes a real difference

Learn more about Chesterwood

The Mount, Edith Wharton’s Home, Lenox

The formal gardens at The Mount are at their most atmospheric in early fall, and the allée of lime trees goes golden in October. The tour of the house connects Wharton’s life as a writer and a designer in a way that stays with you, and the grounds after the tour are worth an unhurried hour.

  • Rating: 4.8 stars (1,249 reviews)
  • Address: 2 Plunkett St, Lenox, MA 01240
  • Admission: Around $23 for adults Best time: September and October for the gardens

Learn more about The Mount

Hancock Shaker Village, Pittsfield

The round stone barn at Hancock Shaker Village is one of the most quietly astonishing pieces of American architecture you will find anywhere, and fall is a beautiful time to walk the 750-acre grounds. The village runs hands-on programs through the season and the harvest events in October draw locals as much as visitors.

  • Rating: 4.6 stars (1,272 reviews)
  • Address: 1843 W Housatonic St, Pittsfield, MA 01201
  • Hours: Daily 11 AM to 4 PM

Fall foliage note: Peak color in the Berkshires typically hits the second or third week of October. The southern Berkshires color up slightly later than the north, which gives you a bit more flexibility when booking.

Learn more about Hancock Shaker Village

Winter: November through March

Winter is the Berkshires that most people skip, which means it is also the Berkshires at its most available. The ski areas are running, a handful of restaurants and inns stay open and feel genuinely cozy, and Naumkeag transforms into something out of a fairy tale.

Naumkeag Winterlights, Stockbridge

From mid-November through early January, the gardens at Naumkeag fill with thousands of lights in a display that has become one of the most popular events in the region. The Blue Steps glow. The pathways wind through illuminated trees and sculptures. It is the kind of thing that sounds like a tourist trap and turns out to be quietly magical. Reserve tickets well ahead.

  • Rating: 4.7 stars (914 reviews)
  • Address: 5 Prospect Hill Rd, Stockbridge, MA 01262
  • Season: Mid-November through early January Note: Sells out on weekends, book as early as possible

Learn more about Naumkeag

Jiminy Peak Mountain Resort, Hancock

The largest ski area in the region, with 45 trails, night skiing, and terrain parks. The learn-to-ski program is strong and the instructors get consistent praise from guests with kids. In slower weather windows, the mountain is genuinely uncrowded in a way that larger resorts never are.

  • Rating: 4.4 stars (1,736 reviews)
  • Address: 37 Corey Rd, Hancock, MA 01237
  • Season: Early December through mid-March

Learn more about Jiminy Peak Mountain Resort

Catamount Mountain Resort, Hillsdale, NY

Catamount sits right on the Massachusetts and New York line, making it the closest ski area to the southern Berkshires. The terrain works for mixed-ability groups and the vibe is relaxed and unpretentious. A good choice if you are staying in Great Barrington or New Marlborough and want a ski day without a long drive.

  • Rating: 4.5 stars (1,414 reviews)
  • Address: 78 Catamount Rd, Hillsdale, NY 12529
  • Best for: Families, mixed-ability groups, a low-key day on the slopes

Learn more about Catamount Mountain Resort

Spring: April through May

Spring is the Berkshires’ best-kept secret. The trails are clear by April, the waterfalls are running at full force from snowmelt, the gardens are waking up, and almost no one is here. If you want the Berkshires without the crowds, this is your window.

Bash Bish Falls, Mount Washington

The tallest waterfall in Massachusetts drops 60 feet into a clear granite pool, and spring is when it is at its most powerful. The snowmelt pushes the volume to its peak through April and into May, and the surrounding forest is just green enough to feel alive without blocking the sky. The hike in is short and the payoff is immediate.

  • Rating: 4.6 stars (531 reviews)
  • Address: Falls Rd, Mount Washington, MA 01258
  • Best time: April and May for peak flow Difficulty: Short but rocky, sturdy shoes required

Learn more about Bash Bish Falls

Berkshire Botanical Garden, Stockbridge

One of the oldest public gardens in the country, the Berkshire Botanical Garden is at its most alive in spring when the first blooms push through and the 24 acres feel like they are waking up in real time. The herb garden, the children’s garden, and the rotating sculpture show are all worth the slow walk, and at around $18 admission it is one of the easiest and most relaxed stops in the southern Berkshires.

  • Rating: 4.5 stars (892 reviews)
  • Address: 5 W Stockbridge Rd, Stockbridge, MA 01262
  • Hours: Daily 9 AM to 5 PM in season Good for: A gentle morning, easy to pair with Chesterwood or the Norman Rockwell Museum nearby

Learn more about Berkshire Botanical Garden

Norman Rockwell Museum, Stockbridge

Rockwell lived in Stockbridge for the last 25 years of his life, and the museum on 36 acres along the Housatonic River holds the largest collection of his original work anywhere. Spring is a particularly good time to come: the grounds are green, the studio opens for the season in May, and the crowds that fill the place in summer have not yet arrived.

  • Rating: 4.8 stars (3,280 reviews)
  • Address: 9 Glendale Rd, Stockbridge, MA 01262
  • Hours: 10 AM to 4 PM, closed Wednesdays Good to know: Studio opens for the season in May, give yourself 90 minutes minimum

Learn more about Norman Rockwell Museum

Make It a Red Cottage Stay

The Berkshires rewards a certain kind of traveler. One who takes the back road, lingers over a second cup of coffee, and chooses a museum on a rainy afternoon without consulting a list. A Red Cottage home is designed for that pace: considered in every detail, generous in space, and rooted in a region we have known well for nearly two decades.

Browse our Berkshires vacation rentals and find the home that fits your season.

Frequently Asked Questions

What is the best season to visit the Berkshires?
It depends on what you are after. Summer has Tanglewood and the full performance season. Fall has foliage and the estate events. Winter is quiet with good skiing and Winterlights. Spring is uncrowded with waterfalls at their peak. There is no wrong answer, only the wrong expectations for the season you pick.

How many days do you need in the Berkshires?
Three nights is the sweet spot for a first visit. That gives you one main event, one outdoor day, and one slower day for a museum or estate without feeling rushed.

Is the Berkshires worth visiting in winter?
Yes, if you know what is open. The ski areas, Naumkeag Winterlights, and a handful of restaurants and inns make for a genuinely cozy long weekend. It is a different trip than summer but a good one.

Can you visit the Berkshires without a car?
Amtrak stops in Pittsfield and buses run from New York, but you will want a car once you are here. The towns are not walkable to each other and the best experiences, the waterfalls, the ski areas, the estates, all require driving.

The Quiet Magic of the Catskills in Spring

Written by Red Cottage on . Posted in Blog, Catskills, Local Activity Guide, Seasonal + Events, Upstate Field Guide.

Every April, the Catskills exhale. Kaaterskill Falls roars back to life, the spring peepers start calling, and Main Streets that felt sleepy in March suddenly hum with farmers markets and weekenders up from the city. It is, quietly, the best-kept secret of upstate New York travel.

From Red Cottage, you are perfectly placed to catch it at its best. The foliage crowds haven’t arrived yet, the trails feel like they belong to the locals again, and if you can visit between mid-April and Memorial Day, you’ll get the Catskills at their most alive and least packed.

Spring Hikes and Waterfalls

April is the single best month of the year for waterfall hikes in the Catskills. Snowmelt sends rivers and creeks rushing over ledges that look like a trickle by August. Two destinations top the list every year.

Kaaterskill Falls

At 260 feet across two tiers, Kaaterskill Falls is the tallest waterfall in New York State and the headliner of any spring trip to the northern Catskills. After a wet April, the upper plunge thunders. There’s a short, easy walk from the Laurel House Road parking lot to the viewing platform at the top, plus a steep stone staircase down to the gorge between the upper and lower falls if you want the full immersion.

  • Rating: 4.8 stars (1,470+ reviews)
  • Address: Hunter, NY 12436
  • Best time: Weekday mornings before 10 AM. The Laurel House lot fills fast on weekends, so be ready to use the Schutt Road overflow lot a half mile down.
  • What to bring: Waterproof hiking boots, microspikes if you’re going in March, and a camera. Trails are slick and muddy through mid-May.

View on Google Maps

Overlook Mountain Wild Forest

Overlook Mountain is the moderate-effort, big-reward hike just outside Woodstock. The roughly 5-mile out-and-back climbs steadily up an old carriage road, passes the eerie ruins of the abandoned Overlook Mountain House hotel, and ends at a fire tower with one of the most spectacular Hudson Valley views in the region. On a clear spring day, you can see the Ashokan Reservoir, the Hudson River, and the high peaks of the southern Catskills.

  • Rating: 4.8 stars (445+ reviews)
  • Trailhead: Bearsville, NY 12409 (Meads Mountain Road, opposite the Tibetan Buddhist monastery)
  • Best time: Mornings in late April or early May once the snow has fully melted off the upper ridge.
  • Heads-up: The parking lot is small and fills early. There’s no water on the trail, so carry your own.

View on Google Maps

Quick tip on mud season

Mid-March through late April is locally known as mud season. The Catskills 3500 Club and DEC ask hikers to avoid trails above 3,000 feet during this window because soft soil damages the tread. Stick to lower-elevation hikes like Kaaterskill, Overlook, or the carriage roads at Mohonk Preserve until things firm up.

Spring Events and Seasonal Traditions

Spring in the Catskills is event season for locals. A few traditions are worth planning a trip around.

Trout Season Opening Day, April 1

If there’s one date that defines spring in the western Catskills, it’s April 1. The opening of trout season turns Roscoe (officially “Trout Town USA”) into the center of the fly fishing universe. The town hosts the Trout About Town scavenger hunt in early April, and local guides line up on the Beaverkill, the Willowemoc, and the upper Delaware. Even if you don’t fish, the riverside towns are at their most charming in the first week of April.

Catskills Cider Fest at Seminary Hill, May

Seminary Hill Orchard & Cidery in Callicoon is a working orchard and the only Living Building Challenge certified cidery in the world, perched on a ridge with views straight down the Delaware Valley. Their spring cider festival pulls in cider makers from across the Northeast and pairs the pours with a seasonal menu from their kitchen.

  • Rating: 4.6 stars (310+ reviews)
  • Address: 43 Wagner Ln, Callicoon, NY 12723
  • Hours: Friday 12-9 PM, Saturday 11 AM-9 PM, Sunday 11 AM-8 PM
  • Phone: (845) 887-4056
  • Don’t miss: The wood-fired pizza, dry ice ciders on tap, and the panoramic deck at sunset.

View on Google Maps

Mohonk Mountain House Tulip Festival, late April through mid-May

Just over the Catskills line in New Paltz, the historic Mohonk Mountain House plants more than 30,000 tulips every spring across its mountaintop gardens. You don’t need to be an overnight guest to experience it, day passes get you onto the gardens, the tea terrace, and the surrounding 70 miles of carriage trails through the Mohonk Preserve.

  • Rating: 4.5 stars (4,280+ reviews)
  • Address: 1000 Mountain Rest Rd, New Paltz, NY 12561
  • Phone: (888) 976-2943
  • Tip: Day passes are limited and sell out on weekends. Book at least a week ahead through the Mohonk website.

View on Google Maps

Spring Towns, Restaurants, and Tasting Rooms

Half the joy of a Catskills weekend is small-town wandering. Here are the stops we send guests to first.

The Heron, Narrowsburg

The Heron sits on Main Street in Narrowsburg with a back deck overlooking the Delaware River, and it’s the kind of farm-to-table restaurant where the menu changes with what local growers can pick that week. The vegan Katsu tofu bowl, the catfish and broccolini, and the honey butter biscuit have all become guest favorites.

  • Rating: 4.6 stars (370+ reviews)
  • Address: 40 Main St, Narrowsburg, NY 12764
  • Hours: Thursday-Friday 5-8 PM, Saturday 12-3 PM, Sunday 11 AM-3 PM (closed Mon-Wed)
  • Phone: (845) 252-3333

View on Google Maps

Catskill Brewery, Livingston Manor

Catskill Brewery brews on a passive-house-certified site in Livingston Manor and pulls a fly-fishing-and-locals crowd that’s quintessentially western Catskills. They open the taproom for the official Fly Fishing Opening Day Ceremony on April 1 with casting lessons, fly-tying demos, and live music.

  • Rating: 4.7 stars (240+ reviews)
  • Address: 672 Old Rte 17, Livingston Manor, NY 12758
  • Hours: Mon, Wed 3-7 PM, Thurs 3-8 PM, Fri-Sat 12-8 PM, Sun 12-7 PM (closed Tue)
  • Phone: (845) 439-1232
  • Try: Their Ratface McDouglas, a guest favorite that consistently sells out.

View on Google Maps

Catskill Art Space, Livingston Manor

A stop on the way to or from the brewery, the Catskill Art Space (CAS) is a free two-story contemporary art museum that anchors Livingston Manor’s Main Street. The permanent installation by James Turrell alone is worth the drive, the rotating shows feature artists like Francis Cape and others working at a serious national level.

  • Rating: 4.8 stars (32+ reviews)
  • Address: 48 Main St, Livingston Manor, NY 12758
  • Hours: Friday-Saturday 11 AM-5 PM, Sunday 11 AM-3 PM (closed Mon-Thu)
  • Phone: (845) 436-4227

View on Google Maps

Beekman 1802 Kindness Shop, Sharon Springs

Just north of the Catskills proper in Sharon Springs, the Beekman 1802 store is a destination unto itself. Their goat-milk skincare line built a national following, and spring is when their Baby Goat Tours kick off, you can sign up for a working farm tour and meet newborn goats. Pair it with lunch in the village of Sharon Springs for a perfect day trip.

  • Rating: 4.6 stars (430+ reviews)
  • Address: 187 Main St, Sharon Springs, NY 13459
  • Hours: Daily 10 AM-6 PM (closed Tuesday)
  • Phone: (888) 801-1802

View on Google Maps

A Sample 3-Day Spring Itinerary

If you want a turnkey weekend, this is the rhythm we recommend to first-time spring visitors.

Friday afternoon: Drive up from the city, settle into your rental, and head to Livingston Manor for an early dinner at Catskill Brewery and a quick walk through Catskill Art Space.

Saturday: Sunrise hike to the Kaaterskill Falls viewing platform. Brunch in Tannersville. Afternoon at Catskill Animal Sanctuary or Meadowbrook Farm depending on the weather. Dinner at The Heron in Narrowsburg.

Sunday: A morning at Mohonk Mountain House for the tulip gardens and a carriage trail walk. Lunch in New Paltz. Wrap up with a stop at the Saugerties Lighthouse on the way home.

This loop covers all four Catskills counties (Greene, Ulster, Sullivan, Delaware) without ever feeling rushed.

Plan Your Catskills Spring Escape

Spring in the Catskills isn’t summer. It’s quieter, rougher around the edges, and a whole lot more rewarding if you come prepared. The waterfalls run hard, the towns feel local again, and the homes we manage are at their cozy best with the woodstove still earning its keep at night.

When you’re ready to book, browse our collection of Catskills vacation rentals or reach out to our team. We’ve been doing this since 2007, and we’d love to help you put together the perfect spring weekend.

Frequently Asked Questions

When is the best time to visit the Catskills in spring?
The sweet spot is mid-April through Memorial Day. Early April gives you the loudest waterfalls and trout opening day, late April through mid-May brings the wildflower bloom and Mohonk’s tulip festival, and the last week of May leans into summer with longer days and full menus at every restaurant.

What’s the weather like in the Catskills in spring?
Highly variable. Daytime highs swing from the upper 30s in March to the low 70s by late May, and overnight lows can still dip below freezing in early April. Pack layers, a waterproof shell, and waterproof shoes. Snow is possible at higher elevations through April.

Is mud season really a problem for hiking in the Catskills?
Yes, especially on high-elevation trails (above 3,000 feet). The DEC and Catskills 3500 Club ask hikers to stay off the high peaks during peak mud season because soft trail tread is easily damaged. Lower elevation hikes like Kaaterskill Falls, Overlook Mountain, the Mohonk Preserve carriage roads, and the Mongaup Pond loop are all good spring choices.

Do I need a car to visit the Catskills in spring?
Effectively yes. Trailways buses serve some towns from the Port Authority in Manhattan, but the trailheads, restaurants, and tasting rooms are spread across hundreds of square miles. A rental car (or your own) makes the trip dramatically easier.

Are restaurants and tasting rooms open in early April?
Most are, with limited hours. Many places run a Thursday-through-Sunday schedule until Memorial Day weekend, when they expand to six or seven days. Always check hours before you go, and reservations are wise on Saturdays even in April.

Is spring a good time to visit the Catskills with kids?
Absolutely. The Catskill Mountain Railroad, Catskill Animal Sanctuary, the easy walk to the Kaaterskill Falls viewing platform, and the boardwalk to Saugerties Lighthouse are all kid-friendly, and the spring shoulder season means smaller crowds at every one of them.

Farms Are Waking Up Around Roxbury

Farms Are Waking Up Around Roxbury: Fresh Finds You Don’t Want To Miss

Written by Rebecca on . Posted in Blog, Catskills, Local Activity Guide, Seasonal + Events, Shops, Upstate Field Guide.

As the seasons shift in the Catskills, the farms around Roxbury begin to come back to life, bringing fresh produce, local goods, and a renewed sense of rhythm to the area. From farm stands to scenic countryside stops, it is the perfect time to explore what makes this corner of the Catskills so special. Make the most of your visit by staying in a Red Cottage home, a comfortable and well designed base for soaking in the slower pace and natural beauty of Roxbury and beyond.

Sunken City Cider
Image courtesy of Bovina Farm & Fermentory

Bovina Farm & Fermentory

Bovina Farm & Fermentory is a working farm and brewery where ingredients are grown and fermented right on site. Expect creative farmhouse ales and a truly local experience, with each pour reflecting the land and seasons around you. It’s the kind of place where you can taste the full process from soil to glass.

Pakatakan Farmers Market

Pakatakan Farmers Market is a local staple that brings together farmers, makers, and fresh seasonal goods in one vibrant space. It’s the perfect spot to browse, snack, and stock up on local favorites while connecting with the community. Pakatakan Farmers Market captures the heart of the region’s agricultural scene in one lively setting.

East Branch Farms Kimchi Harvest

East Branch Farms Kimchi Harvest creates bold, handcrafted kimchi and fermented goods right in the Catskills. A must-try for anyone who loves big flavor and small-batch fermentation, each batch is packed with depth and character. East Branch Farms Kimchi Harvest blends tradition with creativity in every jar.

Farms Are Waking Up Around Roxbury: Fresh Finds You Don't Want To Miss
Image courtesy of Wayside Cider

Wayside Cider

Wayside Cider produces small-batch cider made with carefully grown apples and traditional methods. Their ciders are fresh, complex, and perfect for a slow afternoon spent taking in the orchard surroundings. At Wayside Cider, there’s a real focus on balance, craft, and letting the apples speak for themselves.

Sunken City Cider

Sunken City Cider is a cozy cidery pouring crisp, locally crafted ciders made from regional apples. Stop in for a tasting and enjoy the laid-back, farm-side atmosphere that makes it easy to linger. Sunken City Cider offers a relaxed experience where good cider and good company go hand in hand.

Dirty Girl Farm & Creamery

Dirty Girl Farm & Creamery is a beloved Catskills farm known for its beautiful produce and handmade cheeses. Everything here celebrates thoughtful farming and real flavor, with a strong connection to the land. At Dirty Girl Farm & Creamery, quality and care are evident in every bite.

As farms wake up around Roxbury, the area comes alive with fresh flavors, scenic landscapes, and a slower pace that defines the Catskills experience. From roadside farm stands to local markets, it is the perfect time to explore and reconnect with the season. To fully experience it all, book a Red Cottage stay and enjoy a comfortable, thoughtfully designed home base in Roxbury and the surrounding Catskills.

The Places Making Vermont Trend - What’s drawing eyes across the state

The Places Making Vermont Trend Right Now

Written by Rebecca on . Posted in Blog, Local Activity Guide, Seasonal + Events.

Vermont is trending for a reason, and it starts on the slopes. With legendary ski mountains, charming alpine towns, and some of the best snow in the Northeast, the Green Mountain State is drawing skiers and snowboarders from all over this season. From powder days at Stowe and Killington to après scenes that rival the West, these are the places making Vermont trend right now. And when you’re planning your winter escape, making a Red Cottage Stay your home base means you’re never far from first chair, fresh tracks, and a cozy place to unwind after a full day on the mountain.

The Places Making Vermont Trend - What’s drawing eyes across the state
Image courtesy of Brian Mohr

Mad River Glen

Mad River Glen is one of Vermont’s most iconic ski areas, known for its classic New England terrain and fiercely independent spirit. Located in the Mad River Valley, this skier-only mountain is famous for its challenging trails, legendary single-chair lift, and deep natural snow. For those seeking authentic Vermont skiing with serious character, Mad River Glen delivers a true throwback mountain experience.

Vermont Country Store

A beloved institution since 1946, the Vermont Country Store is a nostalgic destination packed with classic New England charm. With locations in Weston and Rockingham, this iconic shop is known for hard-to-find products, classic pantry staples, maple treats, cozy flannel, and old-fashioned candy. It’s a must-visit stop for anyone exploring Vermont’s small towns and looking for timeless gifts and local flavor.

Von Trapp Brewing

Located in Stowe, von Trapp Brewing brings Austrian-inspired lagers to the heart of Vermont. Founded by the von Trapp family of Sound of Music fame, the brewery pairs crisp pilsners, märzens, and dunkels with sweeping mountain views. With its lively bierhall and outdoor beer garden, von Trapp Brewing is a go-to après-ski destination and one of the top craft breweries in Vermont.

Killington Mountain

Killington Mountain, often called “The Beast of the East,” is the largest ski resort in Vermont and one of the premier ski destinations in the Northeast. With expansive terrain, high-speed lifts, terrain parks, and one of the longest ski seasons in the region, Killington attracts everyone from first-timers to expert riders. Its vibrant après-ski scene and year-round outdoor activities make it a cornerstone of Vermont travel.

Farmhouse Pottery

Based in Woodstock, Farmhouse Pottery is a Vermont ceramics studio celebrated for its handcrafted stoneware and timeless New England aesthetic. Each piece is made using traditional techniques, resulting in durable, minimalist pottery designed for everyday use. A visit to the studio offers a glimpse into Vermont’s thriving artisan culture and makes for a perfect stop while exploring Woodstock.

The Places Making Vermont Trend - What’s drawing eyes across the state
Image courtesy of Hen of the Wood

Hen of the Wood

Hen of the Wood is one of the most celebrated farm-to-table restaurants in Vermont, known for its seasonal menus and hyper-local sourcing. With locations in Waterbury and Burlington, the restaurant showcases the best of Vermont’s farms, forests, and fields. Think locally raised meats, fresh vegetables, and foraged ingredients. It’s a must for food lovers seeking elevated New England dining

Simon Pearce

Simon Pearce is synonymous with Vermont craftsmanship. Known for its hand-blown glass and handcrafted pottery, the brand’s flagship location in Quechee overlooks a scenic waterfall and includes a restaurant and retail space. Visitors can watch glassblowers at work while shopping for elegant home décor, making Simon Pearce one of Vermont’s most distinctive artisan destinations.

The Alchemist

The Alchemist in Stowe is home to Heady Topper, one of the most sought-after craft beers in the country. This award-winning Vermont brewery helped put New England IPAs on the map with its hazy, hop-forward style. With a modern visitor center and a lineup of bold, limited-release beers, The Alchemist is a must-visit for craft beer enthusiasts exploring Vermont.

From first tracks at Killington to craft brews in Stowe and fireside dinners after a day on the slopes, it’s easy to see why Vermont is trending right now. Whether you’re here for ski season, small-town charm, or the food and beer scene that rivals anywhere in New England, the Green Mountain State delivers. Make a Red Cottage Stay your home base to stay close to the action, unwind in comfort, and experience the very best of a Vermont winter getaway.

The Best of Hunter & Windham Mountain, According to Locals

Written by Rebecca on . Posted in Blog, Catskills, Local Activity Guide, Seasonal + Events, Shops, Upstate Field Guide.

Planning a trip to the Catskills? Hunter and Windham Mountain are two of the region’s most loved destinations, known for their ski slopes, scenic hikes, cozy towns, and year-round outdoor adventures. This local’s guide to Hunter & Windham Mountain covers where to eat, what to do, and the hidden gems most visitors miss. Whether you’re here for a winter weekend or a summer escape, making a Red Cottage stay your home base puts you perfectly positioned to explore both mountains while enjoying a relaxed, home-away-from-home experience in the heart of the Catskills.

The Best of Hunter & Windham Mountain, According to Locals
Image courtesy of Deer Mountain Inn

📍 Restaurant at Deer Mountain Inn
Refined seasonal dining led by a James Beard–nominated chef, offering thoughtful plates and an experience worth planning a trip around.

📍 Lucky Catskills
An Asian café serving baos, rice bowls, matcha, coffee, and playful provisions that balance comfort and creativity.

📍 Hotel Lilien
A favorite stop for cocktails and relaxed hangs, blending old-world charm with a welcoming, mountain lodge feel.

📍 Hunter Mountain
A mountain destination centered on skiing, hiking, scenic lifts, and full days spent outdoors.

📍 Windham Mountain
Tubing, skiing, and scenic trails paired with an easygoing village atmosphere that suits long weekends and slow afternoons.

📍 Fellow Mountain Cafe
Known for artisanal coffee, house-baked pastries, and elevated breakfast and lunch offerings in a laid-back setting.

The Best of Hunter & Windham Mountain, According to Locals
Image courtesy of Prospect Restaurant

📍 Prospect
Lodge-style dining with seasonal menus, cozy interiors, and a relaxed atmosphere suited for dinner and cocktails alike.

📍 Babblers
A lively restaurant and bakery at Wylder Windham, serving hearty fare in cozy interiors with an inviting après-ski atmosphere.

📍 Paracasa
A modern pantry and provisions shop offering coffee, pastries, and thoughtfully curated goods for picnics, mornings, and everyday stops.

📍 Shandaken Bake
A cult-favorite bakery drawing lines for naturally leavened breads, pastries, and weekend treats.

📍 Westkill Brewing Tap Room
A farmhouse brewery pouring small-batch beers made with local grains, enjoyed in a laid-back tap room setting.

📍 Bearpen Mountain
A quieter mountain area offering scenic trails, open views, and a slower-paced outdoor experience.

📍 Matilda
A design-forward restaurant serving seasonal dishes in a space that feels modern, thoughtful, and effortlessly inviting.

The Best of Hunter & Windham Mountain, According to Locals
Image courtesy of The Windham Local

📍 Windham Local
A casual neighborhood spot for burgers, fries, shakes, and unfussy meals locals return to again and again.

Looking for where to eat, drink, and explore around Hunter and Windham? This local guide highlights go-to spots for mountain days, great meals, and easy stops, all within reach of a stay at Red Cottage Stay.

Stowe, VT Weekend Must-Do's 3 Day Itinerary

Discovering Why Everyone Loves Stowe, Vermont: A Weekend Itinerary

Written by Rebecca on . Posted in Blog, Local Activity Guide, Seasonal + Events, Shops.

Located at the base of Mount Mansfield, Stowe, Vermont is an ideal destination for a weekend getaway, offering scenic mountain views, charming village streets, and easy access to outdoor adventures year-round. From covered bridges and local cafés to hiking trails and boutique shops, Stowe is best explored at a relaxed pace. Staying in a beautiful Red Cottage home provides a prime location for discovering the area with comfort and convenience. With a welcoming place to return to each evening, this weekend itinerary makes it easy to experience the best of Stowe while enjoying a peaceful retreat in the heart of the destination.

Friday: Arrival & Settling In

Stowe, VT Weekend Must-Do's 3 Day Itinerary
Image courtesy of Cork Restaurant

Settle into your Red Cottage stay in Stowe, Vermont and take a moment to breathe in the mountain air before the weekend begins. Once you have unpacked, head out for a quick provisions run so everything you need is ready back at the cottage and the rest of the weekend can feel easy.

Start with a stop at Commodities Natural Market to stock up on pantry staples and a few locally made treats for the weekend. Then head to Cold Hollow Cider Mill for a sweet pick me up, whether that means fresh cider and warm cider donuts, or a few bottles of hard cider to bring back and enjoy by the fire later on.

When it is time for dinner, make your way to Cork Restaurant for a cozy, elevated meal that feels just right after a day of travel. Wrap up the night back at the Red Cottage, shoes off, lights low, and nothing on the agenda except settling in.

Saturday: Skiing, Shopping, and Après

Stowe, VT Weekend Must-Do's 3 Day Itinerary
Image courtesy of Stowe Mountain Resort

Start the morning with coffee and pastries from Woodland Baking & Coffee Co, a local favorite in Stowe, Vermont for a relaxed start before a full day out. It is an easy first stop whether the day includes skiing or exploring town.

Before heading to the mountain, stop by Edelweiss Mountain Deli to grab sandwiches to bring along. Packing lunch makes it easy to spend more time outdoors while skiing in Stowe, Vermont without needing to head back into town midday.

If skiing is on the agenda, spend the day enjoying the slopes and mountain views that make Stowe one of Vermont’s most popular ski destinations at Stowe Mountain. If not, explore the village instead with stops at Stowe Living and Country Store on Main, two great places to shop for local goods and thoughtful finds.

After a day of skiing or exploring town, consider stopping by The Alchemist Brewery to enjoy one of Stowe’s most well known craft beer destinations. Later in the day, slow things down with a visit to Bear Pond Books to pick up something to read back at the cottage. It is a perfect way to unwind after a full day exploring Stowe.

For dinner, head to von Trapp Brewing & Bierhall for Austrian inspired dishes and house brewed lagers, or choose Idletyme Brewing Company for a lively atmosphere and comfort driven menu.

Sunday: A Slow Morning and One Last Taste of Stowe

Stowe, VT Weekend Must-Do's 3 Day Itinerary
Image courtesy of Lake Champlain Chocolates

Spend the final morning in Stowe, Vermont easing into the day with fresh pastries from Stowe Bee Bakery. It is the perfect stop for a relaxed start, whether enjoyed back at the cottage or with a quiet moment before heading out for the day.

Before leaving town, stop by Lake Champlain Chocolates to pick up a sweet treat to take on the road. Vermont made chocolates make an easy souvenir and a thoughtful way to bring a little piece of Stowe home.

For a final meal in town, head to American Flatbread for farm to table, wood fired flatbread pizza made with locally sourced ingredients. It is a fitting way to wrap up the weekend, offering a laid back lunch that still feels special. After lunch, make the drive home at an easy pace, leaving Stowe, Vermont with mountain views in the rearview mirror and plans already forming for a return trip.

A weekend in Stowe, Vermont offers the perfect balance of mountain adventure, small town charm, and time to slow down. From skiing and local shopping to thoughtful meals and quiet mornings, this itinerary highlights some of the best things to do in Stowe over a weekend. Making a Red Cottage stay your home base allows for easy access to town, nearby attractions, and the surrounding landscape, while still offering a peaceful place to return to at the end of each day. Whether visiting for a ski weekend or a scenic escape, Stowe, Vermont is a destination that invites return visits long after the weekend ends.

Your Guide to Winter in Narrowsburg

How to Spend a Perfect Winter Weekend in Narrowsburg, NY

Written by Rebecca on . Posted in Blog, Catskills, Local Activity Guide, Seasonal + Events, Shops, Upstate Field Guide.

Tucked along the Delaware River in the western Catskills, Narrowsburg, NY is the kind of small town that feels especially magical in winter. Snow covered streets, cozy cafés, and quiet river views make it an ideal destination for a winter weekend getaway, whether you are escaping the city or slowing down for a few restorative days upstate. From crisp morning walks to fireside evenings, Narrowsburg invites you to settle into a gentler pace. When it is time to rest, making a Red Cottage home your place to stay, offering a warm and welcoming retreat that feels as charming as it is comfortable.

Your Guide to Winter in Narrowsburg
Image courtesy of One Grand Books

Friday: Arrival & Settling In

Settle into your Red Cottage stay in Narrowsburg, NY and take a moment to breathe in the quiet of the Delaware River before the weekend begins. Once you have unpacked, head out for a quick provisions run so you can fully relax when you are back at the cottage.

Start with an easy stop at Proper to Go to stock up on pantry staples and a few cozy treats for the weekend. Then swing by Narrowsburg Proper or Narrowsburg Fine Wine to pick up drinks for back at your stay, whether you are in the mood for something bright and chillable or a cozy bottle for a winter night in. Before dinner, pop into One Grand Books to grab a book to curl up with later, because a quiet evening at the cottage always pairs well with a good read.

When it is time to head out and grab dinner, make your way to La Cigogne for a warm, French inspired meal that feels just right after a day of travel. Wrap up the night back at Red Cottage, shoes off, lights low, and nothing on the agenda except settling in.

Your Guide to Winter in Narrowsburg
Image courtesy of Ski Big Bear

Saturday: Hit The Slops + Après Ski

Start your morning early with coffee at Tusten Cup, a Narrowsburg favorite for strong brews and a relaxed local feel. It is the perfect first stop before a day outdoors, giving you time to wake up slowly and take in the winter quiet before heading out.

Before you leave town, pack a lunch to bring with you to the slopes so you can stay out longer without rushing back. From Narrowsburg, the two closest options for winter fun are Ski Big Bear at Masthope Mountain in Pennsylvania and Holiday Mountain in Monticello, both offering skiing and snow tubing that are easy to reach for a day trip. Whether you are carving a few runs, tubing with friends, or simply enjoying the fresh air, having lunch packed lets you make the most of the day and keep things simple.

After a full morning and afternoon in the snow, head back to Narrowsburg for après ski at The Laundrette. Settle in with a well earned drink and a wood fired pizza, letting the warmth and easy atmosphere ease you out of the cold. It is the kind of place that feels especially good after a winter day outside and sets the tone for another cozy evening back at your stay.

Your Guide to Winter in Narrowsburg
Image courtesy of Catskill Curated

Sunday: A Slow Morning and Last Minute Finds

Before you head home, enjoy one last unhurried breakfast at Two Queens Coffee. It is the perfect place to linger over a warm meal and one more cup of coffee, soaking in the easy Sunday morning rhythm before packing up and saying goodbye to Narrowsburg.

On your way out of town, make a stop at Catskill Curated to take a small piece of Narrowsburg home with you. The thoughtfully selected goods and locally inspired finds make for meaningful souvenirs or gifts that capture the spirit of the Catskills. If you came from the city make the drive part of the experience. On your way home, make a stop at Hawk’s Nest near Port Jervis for a quick stretch and a look at one of the most scenic overlooks in the region. The winding road and sweeping views of the Delaware River are especially striking in winter and make for a memorable final moment before heading back.

A winter weekend in Narrowsburg, NY is all about slowing down, embracing small town charm, and making space for simple pleasures. From cozy mornings and snowy adventures to relaxed meals and quiet evenings, it is the kind of getaway that feels both refreshing and restorative. Making a Red Cottage home your place to stay brings it all together, offering a warm and welcoming base to return to after each day out exploring. Whether you are planning a quick escape or a long weekend upstate, Narrowsburg proves that winter is the perfect time to settle in, unwind, and enjoy the Catskills at a gentler pace.

Find the best places to ski in the Northeast, from New York and the Poconos to Vermont, New Hampshire, Maine, Massachusetts, and Connecticut.

Where to Ski in the Northeast: A Regional Guide

Written by Rebecca on . Posted in Blog, Catskills, Hudson Valley, Local Activity Guide, Seasonal + Events, Upstate Field Guide.

Planning a winter getaway in the Northeast is all about location, and choosing the right homebase can make the entire trip better. When you make a Red Cottage stay your homebase, you get the comfort of a private retreat with easy access to some of the best places to ski in the Northeast. From ski areas near New York and the Poconos, beginner friendly trails in Western Mass and Connecticut to classic mountain towns in Vermont, New Hampshire, and Maine, the Northeast offers a wide range of skiing experiences for every skill level. Whether you’re planning a weekend ski trip, a family winter vacation, or a longer mountain escape, these are the top places to ski across the region.

Find the best places to ski in the Northeast, from New York and the Poconos to Vermont, New Hampshire, Maine, Massachusetts, and Connecticut.
Image courtesy of Hunter Mountain

New York & the Poconos (PA): Accessible and Beginner-Friendly

If you’re skiing from New York City, northern New Jersey, or eastern Pennsylvania, this is one of the easiest regions for a Northeast ski trip, especially for weekend getaways.

Why ski in NY & PA:
Close to major cities (ideal for short trips)
Reliable snowmaking for more consistent conditions
A strong mix of beginner and intermediate trails

Where to ski:
Hunter Mountain (NY): A top pick for skiing near NYC, with steeper runs and a lively after-ski scene
Windham Mountain (NY): A polished, family-friendly option with a comfortable, easygoing vibe
Belleayre Mountain (NY): A solid choice for Catskills skiing, offering well-groomed trails, dependable snowmaking, and a relaxed, less crowded atmosphere
Plattekill Mountain (NY): A favorite for locals, known for natural snow, and classic terrain
Catamount Mountain(NY): A unique place to ski on the New York and Massachusetts border, offering long runs, varied terrain, and a convenient option for skiers coming from both the Hudson Valley and western Massachusetts
Camelback Mountain (PA) & Blue Mountain (PA): Great choices for Poconos skiing, especially for first-timers and weekend trips
Ski Big Bear (PA): A convenient option for Poconos skiing, especially for beginners and families, with reliable snowmaking and easy-access terrain

Best for: Beginners, casual skiers, and quick getaways (day trips or weekends)

Find the best places to ski in the Northeast, from New York and the Poconos to Vermont, New Hampshire, Maine, Massachusetts, and Connecticut.
Image courtesy of Sugarbush Resort

Vermont: The Heart of Northeast Skiing

Vermont is often considered the best place to ski in the Northeast, thanks to its mix of big-mountain terrain, reliable winter conditions, and classic ski towns that make a trip feel like a true getaway.

Why ski in Vermont:
Some of the largest ski areas and trail networks in the Northeast
Consistent snowfall (plus strong snowmaking) for dependable winter conditions
Iconic Vermont mountain towns and a fun after-ski scene

Where to ski:
Stowe Mountain: One of the most scenic places to ski in all of Vermont, with a polished vibe and challenging terrain
Killington Peak: Famous for one of the longest ski seasons in the East and huge variety for all levels
Sugarbush(Mt Abraham): A classic Vermont ski experience with advanced trails and a laid-back New England feel
Jay Peak Mountain: Known for deep snowfall and standout glade skiing for confident skiers and riders

Best for: All skill levels but especially intermediate to advanced skiers

Find the best places to ski in the Northeast, from New York and the Poconos to Vermont, New Hampshire, Maine, Massachusetts, and Connecticut.
Image courtesy of Sugarloaf Resort

Maine: Quiet, Snowy, and Underrated

Maine is one of the most underrated places to ski in the Northeast, offering a true winter feel, fewer crowds, and a big-mountain experience that’s hard to beat if you’re willing to drive a bit farther north.

Why ski in Maine:
Reliable snow and colder temperatures that help keep conditions consistent
Less crowded slopes, even on many weekends
A big-mountain feel with long runs and plenty of terrain to explore

Where to ski:
Sunday River Mountain: One of the largest places to ski in the East, with a huge trail network that works well for mixed-skill groups
Sugarloaf Mountain: A top choice for advanced skiers, known for serious terrain and above-treeline skiing when conditions allow
Saddleback Mountain: A revived classic with a more local vibe, plus great terrain without the bustle

Best for: Experienced skiers and anyone looking for a quieter mountain escape
Heads-up: It’s typically a longer drive than other Northeast ski areas—but the snow, space, and scenery make it worth it

Find the best places to ski in the Northeast, from New York and the Poconos to Vermont, New Hampshire, Maine, Massachusetts, and Connecticut.
Image courtesy of Cannon Mt

New Hampshire: Small State, Big Terrain

New Hampshire delivers some of the best skiing in the Northeast within a compact area, especially in the White Mountains, making it a great choice for skiers who want strong terrain without long travel times.

Why ski in New Hampshire:
Steep, technical terrain that appeals to confident skiers
Shorter drive times compared to Vermont or Maine
A strong mix of modern ski areas and classic New England mountains

Where to ski in New Hampshire
Cannon Mountain: Known for challenging, no-frills skiing and classic White Mountain terrain
Loon Mountain: A popular option for accessible skiing with modern lifts and varied trails
Bretton Woods: Wide, groomed trails that are great for families and relaxed ski days
Waterville Valley: A well-balanced place to ski with lighter crowds and terrain for multiple skill levels

Best for: Intermediate to advanced skiers who want efficient travel and high-quality terrain

Find the best places to ski in the Northeast, from New York and the Poconos to Vermont, New Hampshire, Maine, Massachusetts, and Connecticut.
Image courtesy of Ski Butternut

Western Massachusetts and Connecticut: Easy Access Skiing

If you’re skiing in the western parts of Massachusetts and Connecticut, this region is a great option for easy day trips and low-key winter escapes, especially if you’re looking to avoid longer drives north.

Why ski in MA & CT:
Convenient access from the Hudson Valley, western New England, and nearby cities
A relaxed pace that’s ideal for learning and progressing
Smaller mountains that make for stress-free ski days

Where to ski (Western MA + Western CT)
Ski Butternut (MA): A beginner-friendly place to ski with wide trails and a welcoming atmosphere
Catamount Mountain (MA/NY): Known for longer runs and varied terrain, making it a solid step up for intermediate skiers
Mohawk Mountain (CT): One of the top places to ski in western Connecticut for families and first-timers

Best for: Beginners, families, and anyone looking for an easy, no-rush ski day close to home

Wrap up your Northeast ski trip with the right mix of great terrain and a comfortable place to come back to. From easy day trips near New York City and the Poconos, beginner friendly skiing in Western Mass and Connecticut, to classic skiing in Vermont, New Hampshire, and Maine, there are plenty of memorable places to ski for every level. Make a Red Cottage stay your homebase so you can spend more time on the mountain and more time relaxing after a full day in the snow.

Escape to the Western Catskills A Weekend Itinerary Around Margaretville, Andes, Delhi, and Roxbury

Escape to the Western Catskills: A Weekend Itinerary Around Margaretville, Andes, Delhi, and Roxbury

Written by Rebecca on . Posted in Blog, Catskills, Local Activity Guide, Seasonal + Events, Shops, Upstate Field Guide.

Tucked into Delaware County, the Western Catskills feel quieter and more spacious than their eastern neighbors. Expect winding roads, charming small towns, excellent food stops, and plenty of room to slow down. If you want the kind of weekend that feels both styled and simple, make a Red Cottage stay your home base, then spend your days looping through Margaretville, Andes, Delhi, Bloomville, and Roxbury for food, drinks, and small town exploring.

Friday: Arrival & Settling In

Escape to the Western Catskills A Weekend Itinerary Around Margaretville, Andes, Delhi, and Roxbury
Image courtesy of First Bloom Corner Store

Settle into your Red Cottage rental near Margaretville and take a moment to breathe in the mountain quiet before your weekend begins. Once you’ve unpacked, head out for a quick provisions run so you can fully relax when you’re back at the cottage.

If you’re arriving later in the day, start with an easy stop at First Bloom Corner Store to stock up on pantry gems and a few cozy treats for the weekend. Then stop by Wild Common Wine for a bottle to open back at the cottage, whether you’re in the mood for something bright and chillable, a cozy red for the fire, or a fun pick recommended by the shop.

When it’s time to head out an grab dinner, The Andes Hotel is perfect for a classic Catskills evening, or keep it casual at Wayside Cider with local pours and a laid-back vibe. Wrap up the night back at your stay, fire on, shoes off, and nothing on the agenda except settling in.

Saturday: Skiing and Cozy Meals

Escape to the Western Catskills A Weekend Itinerary Around Margaretville, Andes, Delhi, and Roxbury
Image courtesy of Belleayre Mountain

Start the day slow at your Red Cottage home base, then head into town for breakfast at Cafe Mornings. It’s a cozy, unfussy way to ease into the day before bundling up for winter adventures. From there, make your way to Belleayre Mountain for a few hours of skiing. Whether you’re carving turns or taking it easy, it’s a classic Catskills winter morning.

After skiing, head back toward Margaretville for a late lunch. Café Marguerite is a great option for something warm and relaxed, or stop by Folsom Point Provisions to pick up a few thoughtfully curated bites to enjoy back at the cottage. Spend the afternoon resting by the fire, reading, or taking a quiet winter walk if the weather cooperates.

Ease into the evening with a drink at Oda Wine Garden, then head to Rae’s for dinner. It’s the kind of spot that feels just right after a day outside, with a cozy atmosphere and a meal worth lingering over.

Sunday: A Slow Morning and One Last Stop

Escape to the Western Catskills A Weekend Itinerary Around Margaretville, Andes, Delhi, and Roxbury
Image courtesy of Hollow

Say goodbye to your Red Cottage stay, then head out for a final morning in the Western Catskills. Make your way toward Roxbury for a relaxed breakfast or early lunch at Watershed. It’s an easy, welcoming spot that’s perfect for lingering a little longer, especially if you’re not in a rush to get on the road. Spend some time wandering Roxbury’s main street, popping into shops, or taking a short scenic drive before heading on. If there’s time for a final stop, detour through Delhi and settle in at Hollow for a drink or light bite. It’s a simple, satisfying way to close out the weekend before heading home.

From quiet mornings and ski days to long meals and small town wandering, a weekend in the Western Catskills is all about slowing down and enjoying what’s right in front of you. Using a Red Cottage stay as your home base makes it easy to explore Margaretville and the surrounding towns while still feeling tucked away. Whether you’re here for winter skiing, cozy meals, or just a reset from the city, this corner of the Catskills delivers a weekend that feels both restorative and memorable.

Where to celebrate New Year’s Eve in the Northeast, Hudson Valley, Berkshires, Catskills, Hamptons, and North Fork

Best Places to Spend New Year’s Eve (For Every Kind of Celebration)

Written by Rebecca on . Posted in Blog, Catskills, Hudson Valley, Local Activity Guide, Seasonal + Events, Upstate Field Guide.

If you’re wondering where to celebrate New Year’s Eve, the Northeast is filled with cozy, charming escapes that feel like the perfect way to start the year. From the scenic wineries and historic towns of the Hudson Valley to the snow covered landscapes of the Berkshires, and from elegant seaside celebrations in the Hamptons to peaceful countryside retreats, these destinations offer something for every style of NYE. Whether you are planning a festive night out or a quiet reset, welcoming the new year with a cozy Red Cottage stay, complete with a warm fireplace and winter views, creates a calm and meaningful beginning to January.

Where to celebrate New Year’s Eve in the Northeast, Hudson Valley, Berkshires, Catskills, Hamptons, and North Fork

📍 Klocke Estate
Celebrate New Year’s Eve at Klocke Estate with a polished, countryside night out that feels equal parts festive and elevated. Their NYE programming is designed for a full evening experience, from cocktails and dinner vibes to a midnight moment worth dressing up for.

📍 Lasting Joy Brewery
A “reasonably-timed celebration” that’s still a seriously fun way to ring in the new year. Stop by for the 6pm ball drop, plus complimentary toasts (beer or sparkling cider) and seasonal food and drink specials throughout the day.

📍 Hunter Mountain Resort
If you want classic NYE winter magic, Hunter Mountain brings the spectacle. Expect live music and a DJ plus a torchlight parade and a fireworks finale.

📍 Bearsville Theater
For a music-forward New Year’s Eve in Woodstock, Bearsville Theater is the move. It’s a beloved Catskills venue with big atmosphere and a night-out feel that’s perfect for counting down with live music (check the event listing for the latest lineup and timing).

📍 Southampton Social Club
A high-energy Hamptons NYE with options depending on your vibe. Choose from packages like open bar + hors d’oeuvres, or level up to four-course dinner seating with party access into the early morning.

Where to celebrate New Year’s Eve in the Northeast, Hudson Valley, Berkshires, Catskills, Hamptons, and North Fork
Image courtesy of The Halyard

📍 The Halyard
Ring in the new year near the water with a full tasting menu, then stay for live music and an NYE party (with set dinner seating windows and music later in the night). It’s a North Fork pick that feels celebratory but still coastal-calm.

📍 Bousquet Mountain
Don’t miss Bousquet’s 3rd annual NYE party, a Berkshires favorite that sells out every year. Expect DJ Adam Oam, a full second-floor lodge takeover, dancing all night, and a complimentary champagne toast at midnight.

📍 Good Night
Start NYE with an incredible dinner at Good Night, where the vibe is warm, intimate, and very “special night out.” They list a New Year’s Eve 2025 menu with a prix fixe and a complimentary champagne toast, making it an easy win for food-first plans.

Whether you’re planning a glitzy night out or a cozy reset, these Northeast escapes make it easy to decide where to celebrate New Year’s Eve. From Hudson Valley wineries and live music nights to Berkshires mountain parties, Hamptons dinner celebrations, and waterfront toasts on the North Fork, there’s an NYE vibe for every kind of traveler. Book early since many events sell out, then make it a full getaway with a Red Cottage stay for a calm, cozy start to the new year.

Litchfield County, Connecticut winter travel guide with scenic snow-covered hills

How to Winter in Litchfield County: Your Guide to Cozy Charm and Snow-Dusted Adventures

Written by Rebecca on . Posted in Blog, Local Activity Guide, Seasonal + Events.

When the snow blankets western Connecticut, Litchfield County transforms into the quintessential New England escape. Forget the city rush and imagine crisp air, stunning snow-dusted hills, and the cozy glow of a tavern fireplace. This isn’t a season to hibernate, it’s the perfect time to explore the charm of the Litchfield Hills. To make your trip seamless and truly feel like home, stay at a Red Cottage property and enjoy the ultimate cozy and convenient basecamp for all your snow-day excursions.

Downhill Skiing and Snow Tubing

Litchfield County, Connecticut winter travel guide with scenic snow-covered hills
Image courtesy of Mohawk Mountain Ski Area

📍 Mohawk Mountain Ski Area
A true Connecticut classic for downhill skiing and snowboarding. Mohawk Mountain is the state’s oldest and largest ski area, offering trails for all levels and reliable snowmaking. It’s the perfect place to turn a chilly morning into a full-on snow day.

📍 Ski Sundown
If you want variety, this spot is known for its excellent conditions, two terrain parks, and great night skiing. It’s ideal for groups looking for reliable conditions and plenty of vertical fun.

Cross-country Skiing, Snowshoeing, + Easy Winter Walks

Litchfield County, Connecticut winter travel guide with scenic snow-covered hills
Image courtesy of Topsmead State Forest

📍 White Memorial Conservation Center
This 4,000-acre preserve offers over 40 miles of trails perfectly suited for cross-country skiing and snowshoeing. If you want a nature-first moment with frozen lake views, be sure to find the scenic vista near the Ice House ruins on the Lake Trail.

📍 Topsmead State Forest
The rolling, snow-covered grounds surrounding the English Tudor-style “cottage” here offer a majestic, quiet setting for a snowy stroll or sledding. It feels like stepping into a peaceful, historic countryside landscape.

📍 Appalachian Trail
Winding through pristine hardwood forest, offering hikers a peaceful escape. Whether for a short walk or longer trek, the scenery and serenity are unmatched on this portion of the Appalachian Trail.

Après-Ski & Cozy Sips

Litchfield County, Connecticut winter travel guide with scenic snow-covered hills
Image courtesy of Litchfield Distillery

📍 Litchfield Distillery
A fantastic destination for post-adventure relaxation. Take a complimentary tour and sample their award-winning small-batch spirits. It’s a great way to taste the local flavor and warm up from the inside out.

📍 Kent Falls Brewing Co.
A local favorite for craft beer lovers. The taproom is welcoming and spacious, perfect for sampling a few brews with friends. Their dedication to quality shines in every pour.

📍 Hopkins Vineyard
Sip on seasonal wines while enjoying stunning views over Lake Waramaug. This is a beautiful pick for a slower, relaxed afternoon that feels special in winter, especially if you can snag a spot near a fire.

📍 The Charming Downtowns (Litchfield, Kent, Washington Depot)
Browse the indie bookstores, antique shops, and local boutiques in these picturesque towns. Duck into a cozy cafe like Marty’s Cafe (Washington Depot) or 45 Main (Kent) to escape the cold and refuel.

Whether you’re here for fresh powder, quiet nature, or a cozy crawl of local shops and taverns, winter in Litchfield County is the kind of getaway that feels both easy and unforgettable. Pick a couple of outdoor adventures, save room for comfort food and local sips, and build a weekend that is equal parts active and laid-back. Then, bring it all back to your Red Cottage stay, your warm, tucked-away escape to unwind, reset, and do it all again tomorrow.

Sullivan County Catskills winter getaway

Winter in the Sullivan Catskills: The Cozy Roundup

Written by Rebecca on . Posted in Blog, Catskills, Local Activity Guide, Seasonal + Events, Upstate Field Guide.

Plan a cozy winter getaway in the Sullivan Catskills with this roundup of the season’s best things to do, from snowy hikes and small-town shopping to warm drinks by the fire and local eats worth the drive. Whether you are planning a romantic weekend or a friends’ escape, you will find cold-weather adventures and indoor favorites that make the region shine. For a stay that feels charming and tucked away, book a Red Cottage home that is well placed for exploring during the day and unwinding at night.

Downhill Skiing and Snow Tubing

Sullivan County Catskills winter getaway
Image courtesy of Holiday Mountain

📍 Holiday Mountain
A classic Sullivan County spot for downhill skiing, snowboarding, and winter tubing that makes it easy to turn a cold day into a full-on snow day. Come for the runs, stay for the family-friendly vibe, and warm up after with a quick bite before heading back out.

📍 Villa Roma’s Ski Hill & Chalet
A cozy, resort-style ski hill where you can do winter the easy way with skiing and snow play all in one place. It is a great pick if you want a low-stress day on the slopes followed by comfort-forward downtime.

📍 Bearpen Mountain Sports
A winter adventure hub for tubing, cross-country skiing, and snowshoeing with a fun, outdoorsy Catskills feel. Perfect for groups who want options, fresh air, and a full day of snow activities without overthinking the plan.

Cross-country Skiing, Snowshoeing, + Easy Winter Walks

Sullivan County Catskills winter getaway
Image courtesy of Bearpen Mountain Sports

📍 Sullivan O&W Rail Trail
A scenic, mostly gentle trail that is ideal for an easy winter walk, a snowy bike-style stroll, or a peaceful cross-country ski when conditions line up. It is a great way to soak up the Sullivan Catskills landscape without committing to a steep hike.

📍 East Mongaup River Park
A quiet, nature-first spot for winter hiking, snowshoeing, and cold-weather wandering along the Mongaup. If you want a calm trail moment with woods-and-river scenery, this is an easy add to your winter itinerary.

📍 Mongaup Pond Area
A go-to winter woods vibe with peaceful trails and that classic frozen-lake feel when the temps drop. It is especially dreamy after fresh snowfall and perfect for a slow, scenic snowshoe or walk.

📍 NYSDEC lands in the area
A choose-your-own-adventure option for winter exploring, since many DEC trails are open for snowshoeing and cross-country skiing. Ideal for travelers who want uncrowded nature, flexible trail picks, and a true Catskills winter reset.

Après-ski

Sullivan County Catskills winter getaway
Image courtesy of Catskill Brewery

📍 Upward Brewing Company
A Livingston Manor favorite for après-ski energy, with craft beer, comfort-forward bites, and a warm, laid-back atmosphere. It is the kind of place you will want to linger, especially after a cold hike or a day on the slopes.

📍 Callicoon Brewing Company
A relaxed riverside-style brewery stop that pairs well with winter weekends and small-town exploring. Swing by for a seasonal pour and an easy meal that feels cozy without trying too hard.

📍 Catskill Brewery
A lively local brewery hangout that is great for post-adventure drinks and casual food in a Catskills setting. Perfect when you want a low-key, group-friendly spot to toast the day and warm up.

📍 Seminary Hill Orchard & Cidery
A Callicoon-area destination for elevated cider, orchard charm, and a cozy bite that feels special in winter. It is a beautiful pick for a slower afternoon, a date-night vibe, or a warm drink with countryside views.

Whether you are here for fresh powder, snowy walks, or a cozy crawl of breweries and cider, winter in Sullivan County is the kind of getaway that feels both easy and unforgettable. Pick a couple outdoor adventures, save room for comfort food and après drinks, and build a weekend that is equal parts active and laid back. Then bring it all home to a Red Cottage home, your warm, tucked-away escape to unwind, reset, and do it all again tomorrow.

Drive-through Christmas light show in the Hudson Valley, New York with glowing tunnels and holiday displays

Must-See Holiday Light Shows in Upstate NY (Drive-Through + Walkable Trails)

Written by Rebecca on . Posted in Blog, Catskills, Hudson Valley, Local Activity Guide, Seasonal + Events, Upstate Field Guide.

Twinkling tunnels, drive-through displays, and walkable winter wonderlands make Upstate NY a favorite for holiday lights. If you are planning a quick night out or building a full itinerary, this guide rounds up the can’t-miss Christmas light shows in Upstate New York, including drive-through experiences and festive strolls with music, treats, and photo-worthy scenes.

Want to make it extra memorable? Turn it into an escape for the whole weekend and stay at a cozy Red Cottage home, so you can see the lights, unwind after, and wake up ready for more holiday fun the next day.

Drive-through Christmas light show in the Hudson Valley, New York with glowing tunnels and holiday displays
Image courtesy of A Frosty Fest

📍 A Frosty Fest (Ulster Park)
A holiday light experience with that extra bit of Hudson Valley flair, featuring a drive-through option and a fun atmosphere that feels like a full seasonal outing. Perfect if you want Christmas lights near Kingston or a winter event in Ulster County that feels more like an experience than a quick stop.

📍 The Wonderland of Lights (Rhinebeck)
A classic Hudson Valley drive-through Christmas light show with big, festive displays and an easy route that works for families, date nights, and group outings. If you are searching for Christmas lights in Rhinebeck or holiday light shows in Dutchess County, this one belongs at the top of your list.

📍 Winter Glow (Wappingers Falls)
A drive-through holiday light show at the ballpark that is simple, fun, and great for a low-stress weeknight plan. Ideal for anyone searching for Christmas lights near Poughkeepsie or holiday light shows in Wappingers Falls.

📍 Holiday Lights in Bloom (Montgomery)
A walk-through holiday light display that is perfect for a relaxed winter stroll with photo spots and a family-friendly vibe. If you want walk-through Christmas lights in the Hudson Valley, this is a great choice for an early evening plan.

Drive-through Christmas light show in the Hudson Valley, New York with glowing tunnels and holiday displays
Image courtesy of Peace Love & Lights

📍 Peace, Love & Lights (Bethel)
A scenic drive-through light show on the historic Bethel Woods grounds that feels festive, nostalgic, and totally road-trip worthy. If you are looking for Christmas lights near the Catskills or holiday lights in Sullivan County, this is an easy pick for a cozy winter night out.

📍 Minard’s Family Farm – Christmas Wonderland Spectacular Village of Lights (Clintondale)
A walk-through Christmas village with lights, seasonal activities, and that full holiday-festival energy. Great for families and anyone looking for a Christmas village in the Hudson Valley that turns one night out into a whole memory.

📍 ERDAJT’s Christmas Light Display (LaGrangeville)
A beloved local drive-by display with a community feel that is perfect when you want something festive without tickets or lines. A great option if you are hunting for free Christmas lights in Dutchess County or a quick holiday lights stop near LaGrangeville.

📍 Christmas on the Farm -Apple Ridge Orchard (Warwick)
A cozy, small-town style holiday stop that pairs perfectly with a weekend in the Hudson Valley, especially if you want lights plus seasonal orchard vibes. The orchard turns into a walking holiday lights display for December.

Whether you do one quick drive-through or turn it into a full weekend of strolls, treats, and twinkly photo stops, you really can’t go wrong. If you want to make it a true reset, escape for the whole weekend and stay at a cozy Red Cottage home so the nights feel festive and the downtime feels just as magical.

Bethel Woods Holiday Market Upstate NY Holiday Market Guide

Top Holiday Markets to Visit This Winter in Upstate NY

Written by Rebecca on . Posted in Blog, Catskills, Hudson Valley, Local Activity Guide, Seasonal + Events, Shops, Upstate Field Guide.

The Hudson Valley comes alive in winter with festive holiday markets packed with handcrafted gifts, small-batch treats, and one-of-a-kind finds you won’t get anywhere else. Whether you’re hunting for the perfect present or looking to support local artists, makers, and small businesses, these markets make winter shopping feel fun instead of stressful. From cozy indoor fairs to twinkling outdoor pop-ups, consider this your guide to the best holiday markets in the Hudson Valley this season. Don’t rush home and book a Red Cottage stay so you can savor the holiday cheer and market hop all weekend long!

📍Cannonball Factory Market
🗓️ November 28-30 December 5-7, 12-14, 19-21
Step into Hudson’s Cannonball Factory for a weekend of local artisans, handmade goods, and festive finds. From unique gifts to tasty treats, there’s something for everyone on your holiday list. Support small businesses while enjoying a cozy, creative atmosphere.

📍Twin Star Orchard Holiday Market
🗓️ Saturdays November 22– December 20
Stroll through Twin Star Orchard’s winter market, where fresh cider, baked goods, and handcrafted gifts await. It’s the perfect place to cross off your holiday shopping list while enjoying scenic orchard views. Don’t miss the chance to meet local makers in a festive setting.

📍Makers Central Holiday Makers Market
🗓️ December 20-21
Makers Central transforms its shared studio warehouse in Tarrytown into a festive holiday market full of handmade treasures and local talent. Expect a scavenger hunt for kids, a family‑friendly cocktail hour, live music, and brunch specials (mimosas for the first 100 guests). It’s a joyful, community‑driven shopping experience that puts local makers front and center.

📍The Farmhouse Project Holiday Makers Market
🗓️ December 13-14
The Farmhouse Project invites you to its beautifully curated holiday makers market in Callicoon, featuring a thoughtful selection of artisans, designers, and makers. Set in the Delaware Youth Center, it’s a spot to discover heirloom-quality gifts and slow‑made treasures. While shopping, you’re supporting local creatives who bring craftsmanship and care to every piece.

📍Basilica Farm & Flea
🗓️ November 28–30
Hudson’s Basilica Farm & Flea transforms into a holiday wonderland with artisanal gifts, vintage finds, and tasty treats. Discover one-of-a-kind treasures while supporting independent makers and local entrepreneurs. Perfect for a leisurely day of festive shopping.

📍Troutbeck Holiday Bazaar
🗓️ December 6-7
Troutbeck hosts a charming holiday bazaar in Amenia, featuring local artists, craft vendors, and seasonal specialties. Explore unique gifts for everyone on your list while enjoying the historic ambiance. This market is ideal for a relaxed, festive outing.

📍Make Your Mark[et]
🗓️ November 28-December 24
Irvington’s Make Your Mark[et] brings local makers together for a festive day of shopping and community. From handcrafted goods to seasonal treats, it’s a perfect spot for unique holiday gifts. Celebrate the season while supporting Hudson Valley artists.

📍HoliYAY! Market
🗓️ December 13-14
Peekskill’s Yay! Market HoliYAY! Market is full of holiday cheer, handmade gifts, and delicious local goodies. Browse artisan stalls, find one-of-a-kind presents, and enjoy a lively, festive atmosphere. Every purchase helps support small businesses in the Hudson Valley.

📍The Holiday Shoppe by The Floral Society
🗓️ December 14–15
Dobbs Ferry’s Holiday Shoppe is a floral-inspired market featuring handcrafted gifts, seasonal décor, and unique finds. Perfect for last-minute shopping or treating yourself, this market celebrates local creativity. Explore, shop, and support independent makers in a festive setting.

📍Wickers Creek Market, Holiday Edition at HudCo
🗓️ December 13
This vintage + antiques market is moving indoors for the holidays to HudCo at Hudson River Landing in Dobbs Ferry. Think rare collectibles, curated vintage finds, and a handful of makers all under one cozy roof. It’s a perfect stop to score thoughtful, timeless gifts while supporting local curators and artisans.

📍Craft Fest at Stissing House
🗓️ December 13-14
Stissing House hosts its third annual “Craft Feast,” where about 50 makers fill the historic tavern with ceramics, baskets, textiles, knives, and more. You’ll also find live caroling, seasonal broth, and a warm, community‑oriented vibe that feels both timeless and festive.

📍 Bethel Woods Holiday Market
🗓️ November 28–30
Bethel Woods brings back its beloved three-day Holiday Market over Thanksgiving Weekend with more than 75 local artisan and specialty food vendors. This is the perfect place to shop thoughtfully for gifts while supporting regional makers and small businesses.

After a day of exploring the Hudson Valley’s holiday markets, don’t head straight home, extend the festive fun with a cozy Red Cottage stay. Sip hot cocoa, unwrap a little downtime, and let the winter charm soak in while you plan your next market adventure. With so many makers, treats, and twinkling lights to explore, a weekend getaway is the perfect way to make the season feel extra special.

Thanksgiving Guide Hudson Valley

The Perfect Thanksgiving Weekend in the Hudson Valley

Written by Rebecca on . Posted in Blog, Catskills, Hudson Valley, Local Activity Guide, Seasonal + Events, Shops, Upstate Field Guide.

Nestled in the heart of the Hudson Valley, Red Cottage offers the perfect blend of cozy comfort and adventure: the ease of a home-style base, the charm of rural escape, and access to gorgeous scenery, local food, and seasonal events. Spend less time worrying about logistics and more time enjoying what matters: family, friends, gratitude and a little fun.

Wednesday: Arrival & Settling In

Bread Alone Thanksgiving Guide Hudson Valley
Image courtesy of Bread Alone Bakery

Settle into your Red Cottage rental and soak up the quiet before the holiday bustle begins. Once you’ve unpacked, head into town to stock up on local favorites for your feast.

Stop and pick up pies for the big day. We recommend Bread Alone Bakery in Woodstock for their classic apple pie, Montgomery Place Orchards in Red Hook for a crumb-topped fruit pie made with their own produce, or Rosie’s General in Kingston for a little bit of everything, pies, baguettes, bagels and any other last minute groceries. Most spots take preorders, so check ahead for hours.

After your pie run, enjoy a casual dinner in town. Grab wood-fired pizza and a local cider at Twin Star Orchard’s in New Paltz or tuck into comforting seasonal dishes at SILVIA in Woodstock. End the evening back at your cottage with a fire and a glass of wine or hot cider to toast the weekend ahead.

Thursday: Turkey Trot + Thanksgiving Feast

Turkey Trot Thanksgiving Guide Hudson Valley
Image courtesy of Ekaterina Novitskaya

Kick off Thanksgiving morning with the Woodstock Turkey Trot, a fun 5K run and walk that starts right in the village center. Afterward, refuel with breakfast at Pearl Moon or Moonrise Bagels, both local favorites for hearty morning plates, fun bagels and great coffee.

Spend the afternoon at the cottage cooking your feast or relaxing by the fire while the kitchen fills with all the best smells of the season. When it’s time for dessert, you’ll be glad you picked up those local pies.

If you’re looking to stretch your legs later in the day, take a drive through Overlook Mountain Trailhead or stroll the Ashokan Rail Trail, where the late-autumn light over the reservoir is picture-perfect. End the evening cozy inside, playing board games or watching a movie with leftover pie.

Friday: Farm Stands + Small-Town Shopping

Wallkill View Farmstand Thanksgiving Guide Hudson Valley
Image courtesy of Wallkill View Farm Market

Sleep in a bit, then head out for brunch at Cafe Mutton in Hudson or Gracie’s Luncheonette in Leeds, both known for locally sourced menus that highlight Hudson Valley farms.

After brunch, explore the area’s best farm stands. Wallkill View Farm Market in New Paltz has incredible local produce and baked goods, while DuBois Farms in Highland offers a market, hard cider tasting, and scenic views. Stop for some fresh-pressed cider, local cheese, and jams to bring back to your cottage.

Spend the afternoon wandering through charming downtowns like Rhinebeck, Hudson, or Phoenicia, browsing artisan shops and early holiday markets. For dinner, make a reservation at Miss Lucy’s Kitchen in Saugerties or enjoy a big dry aged steak at The Phoenician Steakhouse.

Saturday: Scenic Sips + Cozy Evenings

Shandaken Bake Thanksgiving Guide Hudson Valley
Image courtesy of Shandaken Bake

Start your day with a light breakfast at the cottage or pastries from Shandaken Bake, then head out for a short hike or scenic drive. Try Minnewaska State Park Preserve near New Paltz for breathtaking overlooks or Poets’ Walk Park in Red Hook for an easy trail with views of the Hudson River.

In the afternoon, it’s time for some local sipping. Stop by Klocke Estate in Hudson for brandy and sweet vermouth made on-site, or visit Westwind Orchard in Accord for wood-fired pizza and organic hard cider in a rustic-chic setting. If you’re more into beer, Arrowood Farms in Accord brews excellent farmhouse-style ales and often hosts live music on weekends.

Back at your cottage, cook a relaxed group dinner or enjoy leftovers by the fire. End the evening stargazing on the deck or playing cards indoors while the night settles around you.

Sunday: Slow Morning + Farewell

Village Coffee and Goods Thanksgiving Guide Hudson Valley
Image courtesy of Village Coffee and Goods

Take your time on Sunday morning with one last breakfast together. If you’re heading south, stop at Village Coffee and Goods in Kingston or Josie’s Coffee Shoppe in Saugerties for a cozy sendoff.

Before you hit the road, pop into a local farm stand like Greig Farm in Red Hook to pick up maple syrup, local honey, or jam as souvenirs from your Hudson Valley Thanksgiving weekend.

A Thanksgiving to Remember

Whether you’re running the Woodstock Turkey Trot, tasting cider at Westwind Orchard, or just relaxing fireside at your Red Cottage stay, Thanksgiving in the Hudson Valley is pure magic. With farm-fresh food, cozy small towns, and beautiful scenery at every turn, it’s the perfect mix of celebration and calm before the holiday season begins.

Hiking in the Berkshires

Berkshire Trails Worth the Trek: Best Fall Hikes

Written by Rebecca on . Posted in Blog, Local Activity Guide, Seasonal + Events, Upstate Field Guide.

Fall in the Berkshires is magical, with crisp air, vibrant foliage, and trails that wind through some of the region’s most breathtaking scenery. Take your time on these hikes, soak in the colors, and make it a full weekend getaway with a cozy stay at a Red Cottage home. From challenging peaks to peaceful forest paths, these trails showcase the season at its finest.

Bash Bish Falls

Hiking Trails list, Berkshires
Image courtesy of Samuel Quek

📍Falls Rd, Mt Washington, MA
A classic fall destination, Bash Bish Falls delivers a stunning waterfall surrounded by vibrant foliage. This 2.1-mile hike is moderate, with a few inclines that make the view at the bottom even more rewarding. Take your time and enjoy the sound of cascading water as the leaves blaze in autumn colors. Perfect for soaking in scenery without rushing.

The Cobbles Lookout via the Appalachian Trail

📍Furnace Hill Rd, Cheshire, MA
The Cobbles offers sweeping views of the Berkshires and Taconic Mountains. This 1.7-mile moderate hike is short but steep in sections, making it a satisfying climb for a morning adventure. Pause at the lookout to catch the colorful canopy stretching across the hills.

Alander Mountain

📍162 East St, Mt Washington, MA
Alander Mountain’s 5.8-mile moderate trail is ideal for a half-day adventure. The route winds through forests and rocky ridges, rewarding hikers with panoramic vistas at the summit. Enjoy the crisp fall air as you trek this scenic mountain trail.

Mount Race and Race Brook Falls

📍716-732 S Undermountain Rd, Sheffield, MA
Race Brook Falls is a 5.7-mile hike that combines a challenging climb with a stunning payoff. Steep inclines and rocky terrain make it a trail for more experienced hikers, but the cascading waterfalls framed by fall foliage are worth every step. A full morning or afternoon of adventure.

Mount Greylock via Bellows Pipe Trail

📍1200 Notch Rd, North Adams, MA
The highest peak in Massachusetts deserves a hike with a bit of challenge. At 5.9 miles and hard difficulty, this trail climbs steadily to Mount Greylock’s summit, offering sweeping autumn vistas. Take your time and savor a weekend escape with a Red Cottage stay nearby.

Appalachian Trail: Jug End Rd to Mount Bushnell

Hiking Trails list, Berkshires
Image courtesy of Janez Fabijan

📍256 Guilder Hollow Rd, Egremont, MA
This 3.6-mile moderate section of the Appalachian Trail is perfect for hikers seeking a manageable trek with rewarding views. Gentle inclines and forested paths make it ideal for a half-day hike in vibrant fall colors.

Monument Mountain via Hickey & Peeskawsa Peak Loop

📍546 Stockbridge Rd, Great Barrington, MA
A 2.4-mile moderate loop packs in striking rock formations and summit views over the Housatonic Valley. The trail has some steep spots but remains very accessible, making it a favorite for quick hikes with dramatic scenery.

Laura’s Tower Trail

📍2 Park St, Stockbridge, MA
Laura’s Tower Trail is a 1.8-mile moderate hike that climbs to a charming stone tower with panoramic views. The trail is perfect for a short morning outing, allowing plenty of time to linger and soak in autumn’s full spectacle.

Olivia’s Overlook and Charcoal Trail

📍Yokun Ridge South, Hiking Trails, West Stockbridge, MA
This 1.7-mile moderate loop is ideal for a leisurely fall hike with colorful forest views and peaceful overlooks. A short, manageable trek that gives a sense of adventure without requiring a full-day commitment.

Umpachene Falls

📍Umpachene Falls Rd, New Marlborough, MA
A tiny gem, Umpachene Falls is only 0.3 miles and easy for all skill levels. This short trail delivers big rewards with cascading water and brilliant fall leaves—a perfect quick stop on a weekend getaway.

Burbank Trail

Hiking Trails list, Berkshires
Image courtesy of Greg Garnhart

📍Richmond Mountain Rd, Richmond, MA
A 3-mile moderate hike through wooded terrain, the Burbank Trail offers a peaceful retreat into nature. Gentle inclines make it accessible while still providing satisfying autumn vistas along the route.

Explore the Berkshires this fall and take in stunning views, vibrant foliage, and trails for every skill level. After a day of adventure, rest your feet and make it a weekend getaway at a cozy Red Cottage home nearby.

apple picking in the hudson valley

Apple & Pumpkin Picking Spots in the Hudson Valley

Written by Rebecca on . Posted in Blog, Hudson Valley, Local Activity Guide, Seasonal + Events, Upstate Field Guide.

Fall is calling in the Hudson Valley, and there’s no better way to answer than with a basket full of freshly picked apples. From classic family-run orchards to spots with cider tastings and live music, the region is packed with farms ready to welcome you for crisp autumn afternoons. Grab your cozy sweater and get ready to explore the season’s best apple-picking adventures.

Fishkill Farms

Apple picking cider donuts apple cider hudson valley
Image courtesy of Fishkill Farms

📍9 Fishkill Farm Rd, Hopewell Junction, NY
This beloved farm offers more than just apple picking. Think hard cider tastings, hayrides, and a gorgeous hilltop orchard view. With over 100 years of history, Fishkill Farms is especially known for eco-certified apples and fall weekends packed with family-friendly activities.

Clarke’s Family Farm

📍2086 US-44, Modena, NY
A seventh-generation family farm nestled by the Shawangunk Mountains, Clarke’s offers organic and low-spray apples, pumpkins, and more. Open weekends from September 13–October 19, 2025, it’s a perfect spot for a fall outing.

Mead Orchards

📍15 Scism Rd, Tivoli, NY
A classic spot for fall fun, Mead Orchards has pumpkins of every size, a corn maze, and hayrides that make for a perfect family day. While apples are available in season, it’s the vibrant autumn fields that steal the show. Stop by for fresh cider and sweet treats while wandering the colorful farm paths.

Masker Orchards

📍45 Ball Rd, Warwick, NY
A Hudson Valley classic, Masker Orchards has been welcoming families for generations with its 200 acres of pick-your-own apples. Drive right up to the trees, load the car with your haul, and don’t skip the farm store for apple cider donuts and fresh pies. September through October, it’s bustling with fall energy.

Apple Dave’s Orchards

📍82 4 Corners Rd, Warwick, NY
Apple picking here comes with a little extra charm: stroll through the orchards, sip fresh cider, or enjoy live music in the autumn air. Apple Dave’s Orchards is set up for relaxed afternoons with plenty of food, drinks, and entertainment alongside the apple rows.

Greig Farm

Pick your own apples in the hudson valley
Image courtesy of Greig Farm

📍227 Pitcher Ln, Red Hook, NY
Since 1942, Greig Farm has been a go-to for seasonal pick-your-own, and apples shine brightest from September into October. The farm stand keeps things festive with cider, treats, and local goods, making it an easy stop for families and weekend travelers alike.

DuBois Farms

📍209 Perkinsville Rd, Highland, NY
DuBois Farms is a family-friendly destination offering pick-your-own apples, peaches, and more. Enjoy fresh cider donuts, homemade pies, and a variety of beverages at their on-site tavern.

Minard’s Family Farm

📍250 Hurds Rd, Clintondale, NY
Apple season at Minard’s is packed with activities, from corn mazes and wagon rides to a pumpkin patch and petting zoo. The orchard grows dozens of apple varieties, ensuring something is always ripe to pick from early September into October.

Harvest Moon Farm

📍130 Hardscrabble Road, North Salem, NY
Harvest Moon Farm is a fall favorite for pumpkins, corn mazes, and farm-fresh fun. While apples make a seasonal appearance, it’s the sprawling pumpkin fields and festive autumn activities that draw families from near and far. Grab a cider donut, hop on a hayride, and soak in the vibrant fall colors.

Hurds Family Farm

📍2187 NY-32, Modena, NY
A family favorite, Hurds offers apple picking alongside outdoor play zones, bounce pillows, and hayrides. It’s as much about the autumn experience as it is about the fruit, making it perfect if you’re heading up with kids.

Rose Hill Farm

📍19 Rose Hill, Red Hook, NY
Rose Hill Farm is a 100-acre family-run orchard blending old-fashioned pick-your-own charm with a modern cidery. Visitors can pick a wide variety of apples, then settle in for small-batch cider tastings while soaking up sweeping Hudson Valley views.

Twin Star Orchards

Pick your own apples, cider, woodfired pizza, tasting room hudson valley
Image courtesy of Twin Star Orchard

📍155 N Ohioville Rd, New Paltz
Apple picking meets serious foodie vibes at Twin Star. After filling your bag with crisp apples, stay for wood-fired pizza, burgers, and cider tastings. Live music and laid-back orchard views make it a perfect fall hangout.

Wright’s Farm

📍699 NY-208, Gardiner, NY
Wright’s Farm is a sixth-generation farm offering pick-your-own apples from September to early November. No reservations are required, and dogs are welcome.

Cedar Heights Orchards

📍8 Crosby Ln, Rhinebeck, NY
Cedar Heights Orchards mixes pumpkins, squash, and seasonal produce with a cozy farm vibe. Kids love the hayrides, petting areas, and photo-ready pumpkin patches. Stop by for baked goods and fresh apple cider.

Stone Ridge Orchard

📍3012 NY-213, Stone Ridge, NY
Stone Ridge Orchard has become a go-to for pumpkins, hayrides, and festive fall events. While they do have a few apple trees, most visitors come for the seasonal pumpkins and farm experiences. Grab a spiced cider and enjoy the autumn scenery.

Samascott Orchards

📍5 Sunset Ave, Kinderhook, NY
Samascott Orchards is a family-friendly farm where pumpkins, gourds, and seasonal fun take center stage. Apple picking is available, but the sprawling pumpkin fields and farm activities like hayrides make it a top fall destination. Don’t miss their fresh-pressed cider and bakery treats.

Kelder’s Farm

Kelder's Family Farm Map Upstate NY
Image courtesy of Kelder’s Family Farm

📍5755 US-209, Kerhonkson, NY
Kelder’s Farm is more than a pumpkin patch, it’s a full fall adventure. Pick your perfect pumpkin, navigate the corn maze, or grab a cider donut while taking in the stunning valley views. Seasonal apples are also available, but this farm shines brightest when the leaves turn.

Lean into fall and turn apple picking into a full weekend escape in the Hudson Valley. Stay in a Red Cottage home and make the most of crisp mornings, scenic drives, and charming farm towns. Pack your favorite sweater, plan a long autumn weekend, and soak up all the colors, flavors, and cozy vibes the season has to offer.

View of the printing room at Woodstock School of Art

The Can’t-Miss List for Upstate Art Weekend

Written by Rebecca on . Posted in Blog, Catskills, Hudson Valley, Local Activity Guide, Seasonal + Events, Upstate Field Guide.

Every summer, Upstate Art Weekend transforms the Hudson Valley and Catskills into one big open-air gallery. With exhibits tucked into barns, performances in meadows, and studios opening their doors, it’s the perfect excuse to hit the road and see what’s blooming beyond the city. Let this be your guide to the region’s most compelling creative moments.

Foreland Open Studios

Aerial view of Foreland
Image courtesy of Foreland

📍111 Water St, Catskill, NY
Foreland’s annual Open Studios is a highlight of the weekend, with three buildings full of working artists inviting you into their creative worlds. Meet painters, sculptors, and makers where the magic actually happens. Grab a coffee from Willow located in the building and spend a few hours wandering.

Harold Stevenson Art Omi

📍1405 County Route 22, Ghent, NY
Less Real Than My Routine Fantasy is a sweeping survey of works by Harold Stevenson, best known for his bold explorations of masculinity, beauty, and queer identity. Spanning decades of his practice, the show invites viewers into a deeply personal and often provocative world. Set within the striking architecture of Art Omi‘s gallery, it’s one of the weekend’s most compelling solo exhibitions.

Macedonia Institute x Ten Barn Farm

📍1142 County Route 22, Ghent, NY
Macedonia Institute brings its curatorial edge to Ten Barn Farm, pairing contemporary works with wide-open skies and rolling pastures. The space itself blurs the line between installation and landscape. It’s a thoughtfully layered show in a setting that begs you to slow down and take it all in.

The Campus

An art installation at The Campus
Image courtesy of The Campus

📍341 NY-217, Hudson, NY
Just across the bridge from Foreland, The Campus hosts a series of rotating exhibitions across several artist-run spaces. It’s experimental, engaging, and packed with emerging talent. Definitely worth a detour (or a deep dive).

Mary MacGill Sculptural Jewelry Exhibit

📍212 Main St, Germantown, NY
Jewelry becomes sculpture in this special exhibit at Mary MacGill’s sunlit studio. Known for her organic forms and delicate goldwork, MacGill presents new pieces that blur the line between adornment and art object. A must-see for design lovers.

Noisemakers Dance Party at Assembly

📍236 Wall St, Kingston, NY
Noisemakers Dance Party is the official kickoff event for Upstate Art Weekend, a celebratory evening that doubles as a fundraiser for abortion access. With beats from Andy Pry of Tiki Disco and Lovetempo (Mattie Safer of Poolside / The Rapture), the vibe is electric and inclusive. It’s the perfect way to dance into the weekend and show some love for a cause, 100 % of proceeds benefit reproductive justice.

Art21 Screening + Artist Talk at Catskill Art Space

Girl standing in front of art work
Image courtesy of Art21

📍48 Main St, Livingston Manor, NY
Settle in for a special screening by Art21, showcasing followed by short documentary films on the artistic practices of James Turrell and Arlene Shechet, both of whose work will be on view at CAS. After there will be artist talk and community conversation. The space is intimate and the programming always sharp. A great way to connect with the ideas behind the work and the people making it.

Art Fair at Woodstock School of Art

📍2470 NY-212, Woodstock, NY
This juried art fair brings together regional talent across mediums, all set against the historic backdrop of the Woodstock School of Art. Browse paintings, prints, sculpture, and more while mingling with artists on site. It’s casual, community-driven, and full of fresh finds.

Upstate Art Weekend offers something for every kind of art lover, from immersive installations and intimate screenings to lively dance parties and open studios. Whether you’re chasing inspiration or just looking to soak in the creative energy, these events invite you to experience the region in a fresh, vibrant way. Plan your route, gather your crew, and get ready to dive deep into a weekend where art is everywhere you turn. Book a Red Cottage getaway and turn your art-filled weekend into a true retreat.

Bethel Woods Center for the Arts

Summer Sounds: The Festivals Worth Traveling For

Written by Rebecca on . Posted in Blog, Catskills, Hudson Valley, Local Activity Guide, Seasonal + Events, Upstate Field Guide.

The Northeast brings a rhythm all its own. Live music echoing through valleys, stages tucked into forests and fields, and towns that come alive with energy and sound. These festivals offer more than just a great lineup; they’re a reason to explore, connect, and celebrate the season. Here are our top music festivals worth traveling for.

Grey Fox Bluegrass Festival

Aerial view of the bluegrass festival
Image courtesy of Grey Fox Bluegrass Festival

📍Location: 1 Poultney Rd, Oak Hill, NY
Grey Fox Bluegrass Festival has been a summertime staple for decades, drawing legends and newcomers alike to its scenic hillside stages. Camp under the stars, catch a sunrise jam session, and experience one of the most joyful weekends in the Catskills. It’s more than music, it’s tradition.

Meadowlark

📍Location: Stone Ridge Orchard, Stone Ridge, NY
Meadowlark is a newer festival, but it already feels essential. This thoughtfully curated gathering blends music, poetry, and nature into a day of gentle magic. With scenic views and a slow-paced schedule, it’s perfect for those who like their festivals soulful and serene.

Woodsist Festival

festival poster
Image courtesy of Woodstist Festival

📍Location: Arrowood Farms, Accord, NY
Woodsist Festival brings indie rock’s warmest hearts and coolest bands to a laid-back Catskills farm. Hosted by the folks behind Woodsist Records, it’s a low-key, high-vibe weekend of live sets, local beer, and open fields. Think of it as your dream backyard show with better sound and scenery.

Hello Inclusion

📍Location: 200 Hurd Rd Bethel, NY
Hello Inclusion is all about celebrating neurodiversity, creativity, and connection. This inclusive festival offers live music, art experiences, and sensory-friendly zones in a setting that feels open-hearted and welcoming. It’s as much about community as it is about the lineup.

Summer Hoot

Festival goers spread out on the lawn watching
Image courtesy of Summer Hoot

📍Location: Ashokan Center, Olivebridge, NY
The Summer Hoot is a family-friendly folk festival set in the woods, where nature and music go hand in hand. There’s something for everyone, from kids’ activities and local food to singalongs and intimate performances from beloved folk musicians. It’s the kind of weekend that fills your cup.

Rosendale Street Festival

📍Location: Main Street, Rosendale, NY
The Rosendale Street Festival turns this small river town into one giant block party. With over 70 bands on multiple stages, local food vendors, artists, and parades, it’s a joyful explosion of creativity. Come for the music, stay for the community spirit.

From bluegrass hillsides to orchard stages and downtown street parties, the Hudson Valley and Catskills know how to throw a festival. Each event offers a unique mix of music, art, and local flavor, with something to discover around every corner. Find your rhythm, grab your crew, and plan a getaway that hits all the right notes.

7 Best Places to Go Skiing Near NYC

Written by Red Cottage LLC on . Posted in Blog, Seasonal + Events.

From the Catskills, the Berkshires, and beyond, residents of New York City will be pleased to know that just outside of our flat city rises a plethora of mountains, many of which are ideal for a winter ski trip. Exchange the sludge of the city streets with small towns, picturesque mountains, and of course, fantastic slopes.

Winter transforms Upstate New York and neighboring Massachusetts and Connecticut into a snow-laden wonderland. Its hills and forests, tranquil and stunning, become magical under fresh snow. Apart from skiing and snowboarding down beginner-friendly up to black diamond runs, many of the best ski resorts in the Northeast offer cross-country skiing, snow tubing, ice skating, snowmobile rentals, and snowshoeing to round out the winter activities.

Although you could visit any of these resorts as a day trip, we highly recommend you stay the weekend. Here at Red Cottage, we’re more than just a vacation rental provider (though our rentals are sublime). We’re your gateway to all of New York State’s wonders, and the best part? Those wonders shine ever so brightly in the winter season. Known for exceptional rentals and deep local insights, we ensure every stay is comfortable and an authentic experience. 

To highlight the area’s appeal to skiers, we’ve rounded up the seven best places to go skiing near NYC so you can plan your perfect winter escape.

1. Hunter Mountain

Photo Credit: James Kirkikis
  • Address: 64 Klein Ave, Hunter, NY 12442
  • Best for: Advanced skiers and snowboarders who value a challenge.
  • Distance from NYC: 2 hours

Hunter Mountain, known as “NY’s Big Mountain,” is a top choice for skiing aficionados. Reaching an elevation of 3,200 feet and boasting a 1,600 feet vertical drop, it presents an exhilarating experience across its 320 acres. The resort’s 67 trails cater to all abilities, offering 25% beginner, 30% intermediate, and 45% advanced terrain, complemented by four terrain parks.

Its diverse landscape ensures a thrill for novices and experts alike. In addition to its impressive trails, Hunter Mountain is renowned for its high-speed lifts and state-of-the-art snowmaking, ensuring top conditions throughout the season.

The resort also hosts various events and activities, making it a vibrant destination for more than just skiing. Whether enjoying the lively après-ski scene or participating in winter festivals, Hunter Mountain provides a comprehensive winter experience.

Hunter Mountain is going digital this year with a new app, My Epic, that allows you to access the mountain hands-free. This means once you get your lift ticket, you just need to turn on Bluetooth and you’ll automatically be scanned at the lift so you don’t have to bother taking out your pass at each run. Plus, the app shows lift lines, trail maps, and real-time mountain alerts.

2. Catamount Mountain

Photo Credit: Nick Sweeting
  • Address: 78 Catamount Road, Hillsdale, NY 12529, United States
  • Best for: Families; diverse-leveled skiers
  • Distance from NYC: 2.5 hours

Catamount Mountain Resort is a scenic ski destination just 2.5 hour drive from NYC, situated in the Berkshire Mountains on the New York-Massachusetts border. The resort caters to all levels with its diverse terrain, featuring 36 trails (32 with snowmaking) and four chairlifts, including a summit quad.

Known for value, it offers well-maintained slopes suitable for beginners and advanced skiers. It’s also a family-friendly choice thanks to comprehensive learning programs like Mountain Cats. With its 2,000-foot summit elevation and 1,000-foot vertical drop, Catamount is a hidden gem for diverse skiing experiences. It’s also an excellent choice for those seeking a value-for-money skiing experience with various terrains.

For those looking to level up their children’s skiing adventures, Catamount Mountain Resort’s Alpine Race Team is a program designed to get your kiddos confident in their skills, technique, and racing abilities.

Apart from skiing and snowboarding, Catamount also has a brand new Snow Tubing Park open day and night.

3. Ski Butternut 

Photo Credit: Matthew Martinez
  • Address: 380 State Road, Great Barrington, MA 01230
  • Best for: Those seeking a traditional skiing experience without the frills of a modern resort
  • Distance from NYC: 2.5 hours

Ski Butternut is a favorite among ski enthusiasts for its friendly atmosphere and top-notch snowmaking. The resort features well-groomed trails suitable for all skill levels, particularly excelling in beginner to intermediate terrains. 

Ideal for weekend and off-peak visits, Butternut offers a family-friendly environment with quality ski instruction. It boasts over 900 feet of vertical drop, fitting for its southern Massachusetts location, although its layout may be slightly challenging for newcomers.

Butternut offers two terrain parks: Twisted Park and Cruiser Progression Park. If you’re new to terrain parks, start with the Cruiser Progression Park and work your way up.

4. Windham Mountain Club

Photo Credit: Makmorg
  • Address: 19 Resort Drive, Windham, NY 12496
  • Best for: Skiers with a refined palate for Mediterranean cuisine from the resort’s culinary program
  • Distance from NYC: 2.5 hours

Located just a short drive from New York City in the scenic Catskills, Windham Mountain is a winter sports destination offering a rich variety of experiences. Its 285 skiable acres encompass 54 trails, served by 11 lifts, providing a range of skiing experiences from serene beginner slopes to challenging terrains for the advanced.  

On Friday and Saturday, Windham is open for night skiing on 8 of its trails so you can truly get in a full day on the slopes.

Windham Mountain Club does have a 2-day minimum on peak days. While this might hinder you wanting to go for a day trip, it is good news for wait times and uncrowded slopes since those that just want to hit a few runs 1 day will have to go to another nearby mountain to do so.

The resort is especially known for its six terrain parks, catering to all skill levels with features for novices and experts. Windham also houses a notable Ski and Ride School, perfect for beginners, and offers additional attractions like a Tubing Park and on-mountain dining for a well-rounded mountain experience.

5. Plattekill Mountain

Photo Credit: Kyle Tunis
  • Address: 469 Plattekill Road, Roxbury, NY 12474
  • Best for: Families looking for a welcoming, community-focused experience
  • Distance from NYC: 2 hours 45 minutes

Plattekill Mountain, nestled in the Northeastern Catskill Mountains, offers a skiing experience steeped in authenticity and adventure. With its “if you can see it, you can ski it” approach, the mountain invites skiers to explore its varied and often challenging terrain. Known for exceptional glade trails, Plattekill exudes an old-school, local ski atmosphere that resonates with enthusiasts. Despite its modest size, the terrain at Plattekill is deceptively challenging, providing thrills for seasoned skiers.

This mountain is not just about challenging runs; it’s about the community and the simple joys of skiing. Privately owned and operated, Plattekill often hosts local events and races, fostering a sense of camaraderie and family-friendly fun. Its remote location adds charm, offering a quieter, more intimate skiing experience away from the crowds. It’s a place where you can genuinely connect with the spirit of winter sports.

Although this “fiercely independent” attitude might make you feel this mountain is small, Plattekill offers 40 trails, running from a 2 mile-long cruiser run for beginners up to steep double black diamonds. They also have an on-site terrain park for the extra adventurous.

6. Belleayre Mountain

Photo Credit: Colin D. Young
  • Address: Shandaken, NY 12480
  • Best for: Skiing traditionalists and aesthetics who love a gondola experience
  • Distance from NYC: 2.5 hours

Belleayre Mountain offers a blend of modern amenities and traditional skiing experiences. It is the only Catskills resort with a gondola, enhancing accessibility and appeal. Known for excellent snowmaking and grooming, Belleayre ensures consistent snow coverage even in less favorable conditions.

Belleayre’s terrain caters to all skill levels, with challenging steeps and groomed runs, particularly beginner-friendly lower slopes. It’s an excellent choice for families and skiers of all levels who appreciate a mix of easy and challenging runs in a beautiful mountain setting.

For those that plan to hit the mountain often this winter, Belleayre offers a frequent skier card and season passes that can also be used at Gore Mountain and Whiteface Mountain (which hosted the Winter Olympics in 1980).

7. Mohawk Mountain

Photo Credit: joelip via Flickr CC2.0
  • Address: 46 Great Hollow Rd., Conwall, CT 06753
  • Best for: Ideal for beginners who want to ski day and night
  • Distance from NYC: 2.5 hours

Located in the Tri-State Area, Mohawk Mountain is a popular destination for skiers and snowboarders alike. Dubbed the “home of snowmaking,” Mohawk is the oldest and largest ski area in Connecticut. Back in 1947, the founder of Mohawk, Walt Schoenknecht became the pioneer of man-made snowmaking, helping to establish the technology still used on slopes today. Today the mountain is still family-owned.

Nestled in the Southern Berkshires, Mohawk Mountain has an elevation of 1,600 ft with 25 trails to choose from. 12 of these trails are open for night skiing. The runs on Mohawk are a combination of easy, intermediate, and black diamonds but in general, this mountain is geared towards beginner and intermediate riders.

Mohawk Mountain also offers snow tubing to add to the family-friendly winter fun!

Start Your Ski Adventure with Red Cottage

From Catamount’s scenic trails to Belleayre’s unique gondola rides, skiing just outside of Manhattan offers a distinct skiing experience. The rugged charm of Plattekill and the diverse offerings of Windham and Mohawk Mountain enrich this tapestry, creating an idyllic winter haven for all skiers and boarders.

Red Cottage offers the perfect accompaniment to this winter adventure. Our cozy rentals provide a warm, inviting retreat after your snowy escapades, embodying the true spirit of the Catskills. Choosing Red Cottage for your ski getaway means immersing yourself in comfort and the thrill of the region’s enchanting landscapes.

Photo by shutterstock.com/Corri Seizinger

Hudson Valley & the Catskills 4th of July Festivals (2023)

Written by Red Cottage LLC on . Posted in Blog, Seasonal + Events.

Fireworks, hot dogs, family fun, and even baseball games await you in Upstate New York this 4th of July. We might be biased but this is one of our favorite holidays to spend in Hudson Valley and the Catskills. 

While there are plenty of 4th of July activities happening throughout the region, we have our favorites. If you’ll be in Hudson Valley or the Catskills this 4th of July, you won’t want to miss out on enjoying one of these events. 

Fireworks at the Walkway Over the Hudson

Poughkeepsie, NY

Get as close to the fireworks as you can when you watch them from the world’s longest elevated pedestrian bridge. From here, you’ll be able to watch the sky light up over the city of Poughkeepsie as you ooh and ahh at the lights bursting above your head.

This event has limited space and sells out every year so be sure to purchase a ticket in advance if you want to join in on the fun at the Walkway Over the Hudson. Tickets are $25 per adult. Children under 12 enter free but still must reserve their spot.

The walkway will be open to ticket holders starting at 6 p.m. and the show starts at 9 p.m. There will ll be concessions to purchase food and drinks but attendees are also welcome to bring their own small cooler.

July 4th Fireworks & Parade

Saugerties, NY

Spend all day enjoying the 4th of July fun in Saugerties. This quaint town on the edge of the Catskills has all the small town charm you might be craving in a celebration of America’s independence. 

Saugerties will start off its celebration with a parade through downtown at 11 a.m. It’s free for anyone and everyone to join in. Later that day, the Saugerties Stallions, the local collegiate baseball team, will face off against local rivals, the Mohawk Valley Hawks at 6:15 p.m. After the game, the town will kick off their free fireworks show around 10 p.m. 

You’ll be hard pressed to have a better 4th of July in the heart of America than the all day festivities in Saugerties. 

Fourth of July Celebrations

Narrowsburgh, NY

Narrowsburgh kicks off their 4th of July celebrations early this year, with fireworks on Main Street going off Sunday, July 2 at dusk. The fireworks show is open to the public so all who are there for the long weekend are invited to enjoy.

The celebrations continue on July 4th kicking off at 3 p.m. with the Fireman’s Parade through downtown. After the parade, head over to Fireman’s Field from 3:30 p.m. to 8:30 p.m. for a family-friendly celebration. You can expect to enjoy live music, carnival activities & games, food & drink, inflatable slides, and a lot of different vendors. 

If you’re in Narrowsburgh for the 4th of July, this is certain to be a big day of fun for kiddos and adults alike. 

Fire Department Field Days

Margaretville, NY

If a long weekend in Narrowsburgh isn’t enough patriotism for you, the Annual Field Days in Margaretville are just what you need. Starting Thursday, June 29 and ending on Tuesday, July 4, you can pay homage to the good ol’ US of A again and again. 

Fireworks aren’t just one night either but 2, bursting in the sky on Saturday, July 1 and the 4th of July at 9:30 p.m. 

Hosted by the local fire department, this event is free to anyone who wants to join but you will need to pay to play or ride the carnival rides. You can expect rides, food, beer, games, live music, and of course, spectacular firework shows.

Good Old Fashioned Celebration

Windham, NY

The town of Windham is ready for a Good Old Fashioned Celebration rain or shine. They’ll kick off their celebration in the evening at 7 p.m. with a parade. At the end of the parade, you’ll be rewarded with a fireworks show visible from even Windham Mountain if you don’t want to make the trip into town.

The parade will start at Route 296 and run through Main Street. 

Don’t Have Plans Yet?

Don’t have plans in Hudson Valley or the Catskills yet? No worries, there’s still time to book at Red Cottage getaway. Book your stay today!

The Best Summer Music Festivals in Upstate NY (2023)

Written by Red Cottage LLC on . Posted in Blog, Seasonal + Events.

Upstate New York in the summer is deliciously warm and sunny. Everywhere you look, the landscape delights your eyesight with rolling shades of green. With mountains, lakes, rivers, and soft patches of grass around every corner, Upstate NY brings the quintessential joys of summer.

The best part? All the fun summer music festivals. Folk, pop, rock and roll, electronica — you’ll find all sorts of genres at one-day or camping fests around the state. After all, Upstate New York is the home of the infamous 1969 Woodstock Music and Arts Festival. 

The soft drum of a guitar and soulful vocals echo through a forest as you sip on a local brew. The sun is shining and you’re basking in its rays during the day, but flock to a campfire to warm up on the cooler nights. 

Tons of our clients enjoy the area’s music festivals during the day before returning to our gorgeous summer rentals. Historic stone houses, on-site pools, and mountain views are just a few characteristics. 

But you’re here for the music, right? We’ll walk you through this year’s best summer music festivals to plan your trip. And once you’re all worn out and can’t sing along any longer? You’ll retreat back to a Red Cottage property to unwind and indulge on your summer vacay. 

Let’s dive into our list of the best summer music festivals in Upstate NY.

Follow the Arrow Festival 

Photo Credit: tixr

Looking for a family-friendly event where the adults can still enjoy a few cold ones? Accord’s Arrowood Farms, a local brewing company, hosts the annual Follow the Arrow Festival for all ages. Just buy a pair of noise-canceling headphones for the little ones. 

You’ll enjoy electronic-fusion beats with indie rock from names like Rubblebucket, or soulful guitar from Scott Metzger. The festival was originally started by Marco Benevento, a musician based out of Woodstock, NY. His style feels experimental and new-aged, as seen by his fusion of rock, jazz, funk, and other experimental styles — plus, he’s also a talented pianist.

  • Location: Arrowood Farms, 236 Lower Whitfield Rd, Accord NY 12404
  • Notable Feature: Kid-friendly
  • Dates: June 17, 2023

2023 Lineup

  • Marco Benevento 
  • Rubblebucket
  • The Barr Brothers 
  • Scott Metzger
  • The Benevento Family Band 
  • More to be announced!

Soulshine Festival 

Photo Credit: tixr

Arrowood Farms hosts yet another infamous summer festival in upstate New York: the Soulshine Festival. The themes? Sustainability, freedom, and love —- with a side of human connection. The latter is what inspires the festival’s host, Michael Franti and Spearhead, philanthropic and positive tunes. Say hey, anyone?

Ring in the summer with this one-day family-friendly music festival. You can expect to listen to great music with wholesome energy while taking part in the festival’s artisan tastes and crafts. No pets allowed, though. 

  • Location: Arrowood Farms, 236 Lower Whitfield Rd, Accord, NY 12404
  • Notable Feature: Food, crafts, and annual host Michael Franti and Spearhead
  • Dates: July 1, 2023

2023 Lineup

  • Michael Franti and Spearhead
  • Tank and the Bangas 
  • Son Little 
  • The Big Takeover

Outlaw Music Festival 

While Outlaw Music Festival sets up all around the country at various locations, they’ll be stopping along the way in Bethel, New York. Venture to the Bethel Woods Center for the Arts — a 16,000-seat amphitheater world famous for hosting the 1969 Woodstock festival. 

Not only is Bethel Woods Center for the Arts a stunning venue, but it’s also the site of the iconic 1969 Woodstock Festival. Listen to your favorite Americana, country, folk, and roots music while visiting this legendary site. We also appreciate the wide range of affordability. Since not all seats are as good as others, travelers on a budget can enjoy higher seats at a better price. 

  • Location: Bethel Woods Center for the Arts, 200 Hurd Rd, Bethel, NY 12720
  • Notable Feature: 1969 Woodstock nostalgia
  • Dates: July 29, 2023

2023 Lineup

  • Willie Nelson 
  • Nathaniel Rateliff and the Night Sweats
  • Gov’t Mule
  • Kathleen Edwards
  • Particle Kid

Catskill Mountain Jubilee

Photo Credit: catskillmountainjubilee

Blue and purple lights, rustling creeks, and rock and roll are some common themes for the Catskill Mountain Jubilee. This year marks this festival’s third run, featuring a wide variety of genres like hip-hop, rock, and even some electronic music. You’ll see some glow-in-the-dark hula hoops here, for sure! 

This festival takes place on magnificent grounds — Blackthorne Resort, a gorgeous property nestled within the Catskill Mountains. Headliners for this fest include the American jam bands, The Disco Biscuits and Legion of Melvin ft. Karl Denson. 

  • Location: Blackthorne Resort, 348 Sunside Road, East Durham, NY 
  • Notable Feature: RV-friendly, camping festival under the stars
  • Dates: August 10-12, 2023

2023 Lineup

  • The Disco Biscuits 
  • Legion of Melvin ft. Karl Denson 
  • Dogs in a Pile 
  • Desert Dwellers 
  • Space Bacon 
  • Beg, Steal, or Borrow 
  • Rose Ganache 
  • Eugene Tyler Band 
  • The Laura Lee Band 
  • Hilltop 
  • Neupy Hundo 
  • Leila 
  • SM Ink 
  • And more! 

Catbird Music Festival 

Photo Credit: relix

Dreamy orchestra tunes from Band of Horses and happy-feeling Lumineers are a couple of award-winning highlights for this year’s Catbird Music Festival. If you’re into Americana, rock, and soul food, this is the festival for you. 

As the sun goes down, you’ll relish natures hugs from the sweeping forest’s soft hums that echo in between performances. Award-winning names in music like Tyler Childers, The War on Drugs, and Dispatch are also in attendance. It isn’t Woodstock, but the hippie aesthetics and Volkswagen painted vans will surely bring some nostalgia! 

  • Location: Bethel Woods Center for the Arts, 200 Hurd Rd, Bethel, NY 12720
  • Notable Feature: Nature-centric location; one-day and two-day tickets
  • Dates: August 19-20, 2023

2023 Lineup

  • The Lumineers
  • Tyler Childers
  • Trey Anastasio Band
  • The War on Drugs
  • Band of Horses
  • Dispatch
  • Trampled by Turtles
  • Charley Crockett
  • Margo Price
  • Amos Lee
  • James Bay
  • Morgan Wade
  • Johnnyswim
  • Celisse
  • Adia Victoria
  • Allison Russel
  • 49 Winchester
  • The Soul Rebels
  • Briscoe
  • Eggy
  • John R. Miller
  • Madeline Edwards

Cave Mountain Catskills Music Festival 

Photo Credit: cavemountainmusicfest

Looking to jam to indie rock, alternative, and even Grateful Dead covers? Cave Mountain Catskills Music Festival is sure to bring you back to the glory days. New in 2023, it’s being held at the Windham Mountain Resort and offers general admission (GA) tickets, VIP experiences, and contests to meet artists and get awesome merch. 

This music festival takes place in mid-September in the heart of the majestic Catskill Mountains. While you listen to some of your favorite bands, all you have to do is look behind you for an otherworldly view of the mountain landscapes. 

On the main stage, you’ll find a 90’s favorite: Weezer. Other popular names include Sheer Mag, Elijah Wood, and the warm-voiced Courtney Marie Andrews. 

  • Location: 19 Resort Dr, Windham, NY 12496
  • Notable Feature: Island on the sun — need we say more?
  • Dates: September 15 – 16, 2023 

2023 Lineup

  • Weezer
  • Joe Russo’s Almost Dead 
  • Preservation Hall Jazz Band
  • Dinosaur Jr. 
  • Lee Fields
  • Albert Hammond Jr 
  • Courtney Marie Andrews 
  • Sheer Mag 
  • Charlotte Rose Benjamin 
  • Channing Wilson 
  • Matt Sucich 
  • Elijah Wolf 
  • Thunderstorm Artis
  • The Bones of JR Jones 

Woodsist Festival

Photo Credit: woodsistfestival

Woodsist Festival is an indie music festival that featured harpist Mary Lattimore and New Jersey rock band The Feelies, among others. The festival doesn’t have any scheduled dates for the 2023 season, but keep tabs on the website for updates. Usually, this festival takes place in late September. 

  • Location: Arrowood Farms, Accord NY 
  • Notable Feature: Dates are TBA

2023 Lineup

To be announced!

Looking for More Summer Festivals? 

Photo Credit: commons.wikimedia.org

Still haven’t found the right music festival for you? We have a few more here that you may want to look into: 

Rochester International Jazz Festival

  • Location: Rochester, NY
  • Dates: June 21-29, 2023

Great Blue Heron Music Festival 

  • Location: Sherman, NY 
  • Dates: July 5-7, 2023

Grey Fox Bluegrass Festival 

  • Location: Oak Hill, NY 
  • Dates: July 18-21, 2023

Great South Bay Music Festival 

  • Location: Patchogue, NY 
  • Dates: July 20-23, 2023

Borderland Festival 

  • Location: East Aurora, NY
  • Dates: September 21-22, 2023

Featured Image Credit: rawpixel