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Author: Red Cottage

The Berkshires, Season by Season

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 Hamptons Experiences of the Moment

Stretching along the South Fork of Long Island, the Hamptons have earned their reputation not just for the scene but for what surrounds it: miles of open Atlantic beach, a serious art history, working farms that supply the restaurants, and a string of villages each with its own character.

Whether you are drawn by the ocean, the culture, or simply the quality of a summer afternoon, there is always more here than a single trip allows.

And when you are ready to plan your stay, a Red Cottage home puts you at the center of it all, with the space and ease to make every day feel intentional.

Start at the Beach

Cooper’s Beach, Southampton

Cooper’s Beach is one of the most celebrated stretches of Atlantic shoreline in the country, a 500-foot ribbon of pale sand backed by historic shingled estates that carries the energy of a private beach club without any of the membership. The water is clear, the dunes are protected, and arriving with no particular schedule is the right approach.

Ditch Plains Beach, Montauk

Ditch Plains is Montauk’s surfers’ beach, known for a consistent Atlantic break and a sunbleached atmosphere that feels nothing like the more polished stretches to the west. Longboarders, families, and first-timers share the sand comfortably, and for anyone new to surfing, it is one of the most welcoming places on the East End to take a first lesson.

The Cultural Life of the South Fork

Parrish Art Museum, Water Mill

The Parrish Art Museum holds one of the strongest collections of American art focused on Long Island’s East End, housed in a long, low Herzog and de Meuron building that mirrors the surrounding farmland. Works by Fairfield Porter and William Merritt Chase fill its well-lit galleries, and the on-site cafe makes a slow afternoon here easy to justify.

Pollock-Krasner House and Study Center, East Hampton

The Pollock-Krasner House is the preserved home and studio where Jackson Pollock and Lee Krasner lived and worked from 1945, including the paint-splattered floor where Pollock’s drip paintings were made. Open by appointment from May through October, it is one of the quieter and more genuinely moving stops on the East End.

Sag Harbor Whaling and Historical Museum

The Sag Harbor Whaling and Historical Museum is housed in a Greek Revival mansion, filled with harpoons, scrimshaw, ship logs, and a beautifully preserved sperm whale jaw at the entrance. Dense with history and easy to move through, it is the kind of small museum that stays with you, and children tend to love it more than expected.

Where to Eat and Drink

Clam Bar at Napeague, Amagansett

The Clam Bar at Napeague is an outdoor seafood shack across the highway from the dunes, with picnic tables, bright umbrellas, and a lobster salad sandwich on brioche that stays with you long after the summer ends. Best on a sunny afternoon with a cold beer and no particular hurry.

Carissa’s The Bakery, Amagansett

Carissa’s is East Hampton’s most beloved bakery, known for crusty country breads, exceptional croissants, and a morning bun worth rearranging your plans for. Saturday mornings here have the warm, unhurried energy of a neighborhood that knows what it has. Go at opening, or plan to wait.

Wölffer Estate Vineyard, Sagaponack

Wölffer Estate is the Hamptons’ most recognized winery, set among long rows of vines in Sagaponack with a rosé popular enough to ship nationwide. The Friday and Saturday Twilight Jazz sessions, picnic blankets welcome, are among the most pleasurable ways to end a day on the South Fork.

Parks, Gardens, and a Few Good Nights Out

Montauk Point State Park

Montauk Point State Park wraps around the lighthouse and gives you the wildest stretch of the South Fork: rocky beaches, coastal scrub, and trails that wind down to the Atlantic cliffs. In winter, harbor seals gather on the offshore rocks from December through April, and the quiet feels nothing like summer.

The Madoo Conservancy, Sagaponack

The Madoo Conservancy is a two-acre garden in Sagaponack created by the late artist Robert Dash, where painted bridges, architectural topiary, and carefully considered plantings shift through the season. Small but deeply intentional, it is one of the more personal and memorable stops on the East End. Open limited hours from May through September.

Guild Hall, East Hampton

Guild Hall has been the cultural anchor of East Hampton since 1931, with a serious exhibition program and a theater that hosts author readings, summer concerts, and the occasional comedy night. It holds the community together without calling attention to itself. Walk in, see what is showing, and check the calendar.

Make It a Red Cottage Stay

The Hamptons remain one of New York’s most enduring destinations, known for their ocean beaches, serious cultural life, and a summer rhythm that rewards those who know where to look.
Whether you are planning a long weekend or a longer escape, there is always more to discover than a single trip allows.

To make the most of your visit, book a Red Cottage home in The Hamptons and settle into a thoughtfully designed home at the heart of the South Fork.

Frequently Asked Questions

What is the best thing to do in the Hamptons for first-time visitors?
Start with a beach. Cooper’s Beach in Southampton and Main Beach in East Hampton are the easiest introductions to what makes the South Fork special. Pair it with a meal at the Lobster Roll and a tasting at Wölffer Estate, and you have already seen the soul of the place.

How many days do you need in the Hamptons?
Two nights is enough for a relaxed weekend that covers one or two villages. Three to four nights is the sweet spot if you want to also explore Montauk, hit a museum, and have a slow morning at a farmers market.

Are the Hamptons worth visiting outside of summer?
Yes. Spring and fall are arguably the best times to go. The light is gentle, the beaches are open and uncrowded, and most of the wineries, museums, and shops still run normal hours. Winter is quiet but the lighthouse, state park, and a handful of restaurants stay open all year.

Can you visit the Hamptons without a car?
Technically yes (the Long Island Rail Road and the Hampton Jitney both go out from New York City), but you will want a car or a hired driver to move between villages, get to the beaches, and reach Montauk. The towns are not walkable to each other.

The Quiet Magic of the Catskills in Spring

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.