For many, the word Woodstock conjures up images of tie dye, hippies, and free love at the 3-day outdoor music festival… that did not actually take place here. (It actually took place in Bethel, which is about 1.5 hours southwest.) That didn’t stop Woodstock from becoming a bohemian destination though; for many years, the streets were lined in touristy gift stores and head shops.
Though it’s taken awhile for the forces of change to sweep through town, Woodstock’s ever-changing Main Street includes lots of new shops, restaurants, and lodging, making it a definite contender for the coolest destination in the Catskills. Plus, it’s home to one of the best outdoor attractions in the entire Catskills region!
Things to Do in Woodstock, NY: Shopping Main Street, Hike to an Old Mountaintop Hotel, and Hit the Spa
The ruins of what was once a grand hotel can be explored at Overlook Mountain. All photos by Erin Lindsey/Escape Brooklyn.
Once spattered with hippie head shops, Tinker Street (Woodstock’s main drag) has gotten a fresh batch of new boutiques that puts it on high on our list for shopping in the Catskills. Three Turtle Doves is one of such additions, and our favorite new shop in Woodstock. Owner Heather Nicosia has an incredible collection of womens vintage and bohemian-style clothing and accessories that feel at home here. The atmosphere and collection are more upscale than your average vintage shop, which features contemporary designers like Lauren Brinkers and Electric Feathers mixed in with the classics like Patricia Smith.
Other notable shops include Shop Little House, Anatolia Rugs, and The Golden Notebook. Also worth checking out is the town flea market, on weekends in the heart of town behind the public parking lot. Aside from these standouts, there are many other cool shops up and down Main Street–carve out a chunk of a day and discover them yourself.
For those seeking outdoor adventure, the hike at Overlook Mountain is not to be missed. The trailhead is about ten minutes from town, and its loop takes about three hours round-trip, which includes some time at the top for sight-seeing. At the top, there are multiple overlooks of the mountains, including a fire tower with 360º views—as well as hotel ruins from the early 1930’s. A gravel path makes the hike considerably easier to do year-round than others in the area, though be warned, it’s length, elevation gain and crowded trails are a turnoff for many. (Still, 100% #worthit) A less crowded trail nearby with similarly stunning views is Huckleberry Point Trail, located in Elka Park. To fuel up for your hike, stop into Circle W in nearby Palenville for soup or sandwich – or hit Mama’s Boy in Tannersville for a burger and a milkshake afterward.
Go see a show at Levon Helm Studios in Woodstock, NY. Photo: Erin Lindsey/Escape Brooklyn.
Last, it would be a crime to visit Woodstock and not experience the art and music culture here. An institution of Woodstock—and the Catskills, or for any music lover—is Levon Helms Studio. Here, tourists and locals gather to catch live music acts inside a large barn-turned-venue. It recently switched management, and its new owners are doing a great job at bringing in upstate/downstate-appropriate talent. Bob Dylan fans will want to visit Big Pink, where Bob Dylan and The Band recorded The Basement Tapes, and The Band wrote their album Music from Big Pink.
To enjoy the visual arts scene, the lovely outdoor landscape/sculpture park Opus 40 is just ten minutes outside of town. Artist Harvey Fite spent 40 years creating the park, whose stone paths twist and wind around the 6.5 acre property. Another stop is through Byrdcliffe Colony, one of earliest utopian arts colonies in America. Take the self-guided walking tour or simply drive through to appreciate the fantastic architecture throughout the area. Last, back on Main Street, stop into Center for Photography and check out their (free!) galleries. Besides being a non-profit exhibition space, it also serves as a facility housing a darkroom, a digital library, and offers an artist in residency program. Stop in, maybe donate a couple bucks, and spread some love.
Best Restaurants in Woodstock, NY: Our Go-To Spots, plus the Best Bars in Woodstock
A cozy corner at the lovely Silvia in Woodstock, NY. Photo: Erin Lindsey/Escape Brooklyn.
Woodstock has a multitude of great places to eat, with some new gems alongside its old ones. Beginning with breakfast, Mud Club is brilliant, serving up wood-fired bagels with delicious spreads; a variety of pastries and sandwiches round out the menu. For a more traditional grab-and-go bakery, Bread Alone (with numerous locations) is a local staple. Also noteworthy is the delicious Tinker Taco Lab, with option of al fresco or indoor dining at its cozy bar.
For a more upscale sit-down dinner, Silvia is an EB staple, where the beautiful interior design is perfectly matched with its wonderful Nordic-Asian-fusion menu. The restaurant offers three different dining areas: outdoors under a vine-wrapped pergola; its main dining room, lined in teak benches and marble tabletops; or its super-cozy leather & velvet-filled bar room. An open kitchen lets you watch the kitchen staff at work, where much of the food is cooked over an open fire. Just down the street, Good Night is a pan-Asian restaurant owned by the same family as Silvia. Just opened in 2023, highlights include shareable plates, outdoor seating, and a signature cocktail menu.
Last, another gem that’s long established in the Woodstock restaurant scene is Cucina, serving up contemporary Italian food in a historic, restored farmhouse. (Reservations are encouraged for either dinner option.)
Freshly opened Tinker Street Tavern in Woodstock, from the owners of Brooklyn gems like Skinny Dennis and Do or Dive. Photo: Erin Lindsey/Escape Brooklyn.
For such a small town, Woodstock has some great spots to grab a drink. For divey vibes, Tinker Street Tavern was opened by the owners of Brooklyn gems Skinny Dennis and Do or Dive, with an amazing indoor/outdoor space, fun cocktail & food list plus live music. For more a more elevated vibe, try Early Terrible for natural wines and finger foods – or newly opened Small Talk for crafted cocktails and wine, while enjoying the views of town from the large wall of windows. Cheers!
Where to Stay in Woodstock, NY: Our Go-To Rentals and Boutique Hotels
Spanning more than 16 acres, the expansive grounds at Glasco Woodstock offer ample room to roam — with outdoor spaces designed to accommodate up to 16 guests. Photo: Thomas John Agoglia
Once a haven for artists and idealists, Woodstock has evolved into a design-forward destination that still hums with the creative energy of its past. Today, the town pairs its bohemian roots with fresh perspective, thanks to a wave of thoughtful hospitality openings that match the rhythm of its surrounding mountains and Main Street culture.
A few favorites:
- Glasco Woodstock, a striking, black-clad retreat tucked just outside town, with curated interiors, outdoor showers, and floor-to-ceiling forest views;
- The Graham & Co., a laid-back, camp-inspired hotel in nearby Phoenicia with a seasonal pool and fire pits;
- Catskills Cloud House, a modern townhouse within walking distance from Phoenicia’s main strip, and less than 30 minutes from Woodstock.
