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
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
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
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.
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
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
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
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
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.
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
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
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
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.
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
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
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
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.
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.
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.
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.
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).
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.
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!
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.
