Best Things to Do in Woodstock, NY
If you’re searching for things to do in Woodstock, NY, you’ve come to the right place.
The town of Woodstock is best known for its creative arts, rich music history, and deep association with 1960s counterculture. Today, this Catskills retreat honors its bohemian and artistic roots, while evolving into one of the Northeast’s most appealing weekend getaways.
I recently spent three nights in Woodstock celebrating my husband’s birthday. Here’s everything you need to make your trip to Woodstock totally groovy!
Where to Stay in Woodstock, NY
Unless you’re doing a day trip from NYC, you’ll likely be looking for hotels in Woodstock, NY.
Without hesitation, I recommend the Woodstock Way Hotel.
Nestled in the woods alongside Tannery Brook, just steps from Tinker Street, the Woodstock Way Hotel is cozy, rustic yet elevated.
It completely won me over.
It’s like a stylish cabin retreat rather than a conventional hotel.
The in-room record players with vintage vinyl and outdoor firepits with complimentary s’mores packs were a lovely touch.
Above all, what really set it apart were the inclusions: a complimentary coffee bar, in-room beverages, snacks and more.
As someone who works with hotels all the time, it’s these small touches that can made a real difference to your stay.
For a more budget-friendly option, check out the Twin Gables Guest House on Tinker Street.
This bed and breakfast welcomes guests with warm hospitality and a great vibe. And it’s in a great spot, right in the heart of town.
The reviews are consistently wonderful.
Check prices and book your stay at the Twin Gables Guest House on Booking.com →
Things to Do in Woodstock NY
Small but mighty, Woodstock offers plenty to keep you busy for a 2-night trip.
Here are my top recommendations for things to do in Woodstock, NY.
1. Explore Tinker Street
First up on this list of things to do in Woodstock is Tinker Street, Woodstock’s main street.
It’s completely walkable and lined with independent boutiques, art galleries, antique stores, and bookshops.
I love that there are no chains here! Just one-of-a-kind finds.
The Liverpool girl in me really enjoyed checking out Strawberry Fields Woodstock, packed with a curated selection of clothing, home goods and vintage guitars.
I also enjoyed The Golden Notebook, a cute little bookstore that’s been around since 1978.
Don’t miss exploring the Woodstock Waterfall Park, just off Tinker Street.
It’s a hidden gem waterfall where the Tannery Brook cascades over a rock face.
To find it, follow the signs for the Woodstock Way Hotel and walk between the two quirky arts and crafts stores. Petting the resident cats is optional, but highly recommended.
2. Woodstock Artists Association & Museum (WAAM)
Next on this list of things to do in Woodstock is a visit to WAAM.
WAAM has been celebrating Woodstock’s arts community since 1919.
The permanent collection features notable works alongside fresh rotating exhibitions.
It’s free to enter and right on Tinker Street.
The gift shop sells art, prints and ceramics crafted by local artists.
3. Eat and Drink Your Way Around Woodstock, NY
Of course, no visit to Woodstock would be complete without exploring the food and drink scene.
Woodstock punches well above its weight when it comes to dining.
Every restaurant, cafe, and bar we tried was independent…not a chain in sight!
Highlights from our trip included Nirvana Indian Cuisine and Small Talk, a fantastic little bar on Tinker Street.
We ate and drank our way through three nights and barely scratched the surface of what Woodstock dining has to offer.
4. Mower’s Saturday Sunday Flea Market
Also worth your time is the Mower’s Saturday Sunday Flea Market.
It’s a beloved Woodstock institution running every weekend from April through October.
Sadly we missed the opening by a week! But some locals told us it’s well worth a wander.
You can expect an eclectic mix of antiques, collectibles, vintage clothing, and local produce.
Pick up a delicious coffee and pastry from Bread Alone on Tinker Street, and enjoy browsing.
5. Immerse Yourself in Nature
Pull on your hiking boots because the Catskills are right on your doorstep!
Here are my recommendations for places to enjoy some nature.
Kaaterskill Falls
At 260 feet, Kaaterskill Falls (pictured above) is the tallest two-tiered waterfall in New York State.
It’s about 30 minutes from Woodstock. You drive along winding roads that take you deeper into the Catskills.
Park in the designated lot off Route 23A and follow the well-marked trail to the main viewing platform.
It’s an easy, manageable walk suitable for most fitness levels.
We visited in early March and sheets of ice still clung to the rock face, making the falls look spectacular.
🥾 Difficulty: Easy
Ashokan Reservoir
This is a super easy stroll along a 2.7-mile paved walkway.
The reservoir supplies 40% of New York City’s drinking water.
It’s flat, scenic, and suitable for all fitness levels.
🥾 Difficulty: Easy
Overlook Mountain
This is a more challenging hike at just over 2.5 miles, all uphill.
Along the trail, you pass the rather eerie skeletal remains of a 19th century resort hotel with a fascinating history.
At the top you’ll be rewarded with stunning views of the Hudson Valley and the Catskills.
🥾 Difficulty: Moderate
Devil’s Path Trail
I’m not in good enough shape to attempt this trail but everyone we spoke to says it’s spectacular.
It’s one of the most challenging trails in the entire Catskills, with serious elevation changes.
🥾 Difficulty: Challenging
6. Sunfrost Farm
Another Woodstock institution on Tinker Street is Sunfrost Farm. It’s part farm stand, juice bar and café.
Stop in for fresh smoothies, homemade pies and locally sourced produce. They’re open 9 AM to 6 PM daily.
7. Karma Triyana Dharmachakra Monastery
For something completely different, the Karma Triyana Dharmachakra Monastery was an unexpected highlight, located just outside the town of Woodstock NY.
This Tibetan Buddhist monastery serves as the North American seat of the 17th Gyalwa Karmapa.
You can join a free public tour taking you through all the buildings, including the Shrine Room.
Tours run on Saturday and Sunday at around 1pm.
After the tour ends, you are welcome to join a free introduction to meditation class.
The drive up Meads Mountain Road is worth doing, whether or not you visit. Buddhist prayer flags line the route and the mountain views are stunning.
📍 Insider tip: Combine the monastery visit with the Overlook Mountain hike, the trailhead is right next door.
8. Levon Helm Studios
Music lovers should not miss Levon Helm Studios.
The Barn began as the home recording studio of Levon Helm, the drummer of legendary rock group The Band, which performed at the original Woodstock Festival (actually held in Bethel, not Woodstock despite the name)
The only way to visit Levon Helm Studios is by attending one of their upcoming shows.
Outside of show hours, the studio remains closed to the public as it doubles as a private residence.
9. Opus 40
Head 10 minutes from Woodstock to the village of Saugerties and you’ll find another unexpected attraction to check out.
Opus 40 is a 6.5-acre sculpture park, built in an abandoned quarry at the foot of Overlook Mountain.
We visited in late March, just a week or so before the season opens in early April.
You need tickets to visit.
📍 Insider tip: Combine Opus 40 with a visit to Saugerties village. It’s a charming, slightly less touristy alternative to Woodstock with great cafes and independent shops.
10. The World’s Largest Kaleidoscope
Last but not least, while you’re out exploring, make a detour to the World’s Largest Kaleidoscope, about 20 minutes from Woodstock at the Emerson Resort and Spa.
Psychedelic artist Isaac Abrams and his son Raphael designed it, completing the project in 1996. It stands 60 feet tall and 38 feet in diameter.
Admission is $5 per person, free for children 11 and under. If you’re a hotel guest, it’s free.
You can visit Thursday – Monday, 10 AM – 5 PM. Closed Tuesday & Wednesday.
Best Time to Visit Woodstock, NY
Woodstock, NY enjoys four distinct seasons, each with its own appeal.
🌸 Spring is when the town starts to come alive again. Crowds are manageable, prices are lower, and the landscape is genuinely beautiful. Our late March visit exceeded expectations, so don’t discount the off season for a visit.
🌞 Summer is peak season. The town is busy. The hiking trails are at their most accessible and there are watering holes to cool off in. Book accommodation well in advance.
🍂 Fall is Woodstock’s most spectacular season. The Catskills foliage is stunning and the cooler temps make it an ideal time for hiking. Book accommodation early.
❄️ Winter is quiet and uncrowded. Some businesses operate on reduced hours so it’s worth checking ahead. If there’s been recent snowfall, the surrounding landscape is breathtaking. You may need snow chains. Check out the Belleayre Mountain Ski Center.
Where is Woodstock NY?
Woodstock sits in the Catskill Mountains, just under two hours north of New York City. Close enough for an easy weekend getaway, but far enough away to feel like you’ve escaped the city.
Getting to Woodstock, NY
Woodstock is best reached by car.
From New York City, it’s just under two hours via the New York State Thruway (I-87) North. Take Exit 20 at Saugerties, then follow Route 212 west into Woodstock.
Getting Around Woodstock
Once you arrive, you can leave the car keys in your room.
Woodstock is walkable. Tinker Street and everything around it is easily covered on foot.
That said, you will need to jump in the car to visit places like Kaaterskill Falls, Opus 40, and the Karma Triyana Dharmachakra Monastery.
Final Thoughts on Woodstock, NY
Woodstock exceeded every expectation.
It’s the perfect place for a weekend getaway.
The town is small, but there’s more than enough to fill a weekend. I recommend a two nights stay.
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