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!

Woodstock, NY Places to Stay: Our Favorite Boutique Hotels

We most recently stayed at the Herwood Inn, a boutique inn located right in town. Each of its four rooms pay homage to women artists — namely: Arethta Franklin, Carole King, Joni Mitchell, and Stevie Nicks — who have created positive change and continue to inspire generations with their music. Inside the “King Suite” (named after Carole King, one of my forever-lady-idols), there’s a kitchenette; king bed; a clawfoot tub in the bathroom; living room stocked with witty games and puzzles, books, TV, and a curated selection of vinyl (and record player)—plus a private balcony. If some bad weather dictates an indoor day, you won’t get bored here!

Each room has access to the shared outside area, featuring a cedar hot tub, lots of seating, and a wood burning fireplace. There’s also a common indoor space (the “Commune”) with a curated gift shop (think CBD products, cute tees and perfumes), alongside a selection of snacks and beverages.

Woodstock Way is another music-themed hotel, with a variety of lodging options that include both cozy cabins and super-modern suites. Shared areas include a patio overlooking the Woodstock Way waterfall, complete with a fire pit. The lobby is also great for a casual hangout, and where guests can pick up breakfast in the morning. When checking in, don’t miss the events board for a curated list of the best events happening around town! Check out our full feature on Woodstock Way.

It’s also worth noting that both hotels are super convenient for New Yorkers; there’s no car needed. Both options are walking distance from the Trailways Bus stop, which leaves many times from Port Authority daily.

Places to Stay in Woodstock, NY: The Best Airbnbs

There’s no shortage of Airbnbs in the area; in fact, Woodstock’s citizens recently voted to cap them. Don’t worry, we’ve weeded out some favorites for you.

For large groups, you can’t do better than Glasco Woodstock, located on 16 acres and sleeping up to 16 friends and family in six bedrooms. It’s quite a treat to wake up in the house’s main suite, which overlooks a koi pond and beyond that, Overlook Mountain. Two bedrooms upstairs have their own ensuites, while downstairs two additional bedrooms share an additional bathroom. A separate studio is just steps from the main house for even more guests.

All can gather in the enormous living room on cozy couches surrounding the most epic, two-story brick fireplace. Other perks include a big beautiful kitchen with an adjoining screened-in porch, hot tub, multiple firepits, and a hot tub. (All photos in the above gallery are from Glasco Woodstock.)

For smaller groups, check out the Bearsville Cabin, a perfect 1970’s log cabin sleeping up to six. Those willing to glamp (or looking to get in some pool time) will love the comfy accommodations at Cooper Lake Outpost.

Things to Do in Woodstock, NY: Shopping Main Street, Hike to an Old Mountaintop Hotel, and Hit the Spa

The stone structure of a hotel is surrounded by trees and overgrown forest. Overlook Hotel near Woodstock, NY.

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. Just across the street, Pacama Handmade is a showroom and retail space for the work of Cedric Martin and other like-minded artisans working in wood, ceramics and textiles.

Other notable shops include Shop Little House, Anatolia Rugs, Fruition Chocolate, 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. Go for lunch rather than betting on it for dinner–it’s so popular that they often sell out!

For a more upscale sit-down dinner, Silvia is the best new option; its stunning interior design is perfectly matched with its wonderful food. 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. 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 bars, there’s plenty to choose from, especially if you’re a craft beer lover. Just outside of town, Woodstock Brewing has a beautiful taproom serving up great beer and snacks with a side… of board games. It’s a great spot to spend a relaxing, beer-fueled afternoon.

Woodstock has some great spots to grab a drink right in town too; our favorites are the newly-opened Tinker Street Tavern, 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; or Early Terrible for date night vibe, whose selection of natural wines and finger foods will leave you swooning. Cheers!