20 Things To Do In Woodstock, New York

1. See exhibits at Woodstock Artists Association and Museum

While in town, make sure to visit or check out the exhibits at Woodstock Artists Association and Museum. The association dates back to 1919, and the museum serves as a repository of artworks produced by artists in the Hudson Valley Region. Most of these artists are based in Woodstock.

See the best works of art in the museum’s permanent collection. Aside from exhibits, one can also attend art classes organized by the association. Have fun with family members as you learn how to sketch and draw under the guidance of seasoned artists.

Woodstock Artists Association and Museum

Address: 28 Tinker St., Woodstock, NY 12498, United States

Website: Woodstock Artists Association and Museum

Opening hours: Thu - Mon: 12pm - 5pm (closed on Tue & Wed)

2. Climb the Shawangunk Mountains

Shawangunk Mountains, also known as the Gunks, is located near Woodstock. Mountain and rock climbers, bikers, and hikers love to go up this ridge and see the panoramic views below. There are parts that are easy to climb for anyone. Other parts are quite difficult and require guides.

There is a road that leads up the mountain, and if you decide to go this way, you will pass by lush vineyards and more views. If you want to stay the night, you can camp near Shawangunk Ridge State Forest.

Shawangunk Mountains

Address: New York, United States

3. Catch a show at Bearsville Theater

Editor's Note: Photo taken from the establishment's official social account

Listen to live concerts of legendary singers and bands in Bearsville Theater. Aside from music icons, this venue is home to dance and theater productions as well. You will find yourself moving with the rhythm of the music. The performances are excellent. The theater has a bar where you can enjoy a cool bottle of beer or a glass of wine during intermission or after a performance. A cafe is also available for light snacks and coffee.

Newly renovated in 2021, the space is intimate and boasts wonderful acoustics. It is a place where the audience can drown themselves in the sound of their favorite music. The theater has two performance areas that can seat 400 people and a small lounge that can accommodate 75 persons.

Bearsville Theater

Address: 291 Tinker St Woodstock, NY 12409, United States

Website: Bearsville Theater

4. View contemporary art at Elena Zang Gallery

Editor's Note: Photo taken from the establishment's official social account

For art enthusiasts, a visit to Elena Zang Gallery is a must. Located amid a lovely garden, the gallery displays contemporary art, photography, works on paper, and paintings. You can view framed pieces with rich splashes of colors inside, while sculptures and ceramics adorn the garden.

These works of art are done by regional and international artists. Some of the ceramics are made by the gallery owners. They also have a studio in the gallery, and visitors can watch artists skillfully make unique ceramic pieces.

Elena Zang Gallery

Address: 3671 NY-212, Bearsville, NY 12409, United States

Website: Elena Zang Gallery

Opening hours: 11am - 5pm (daily)

5. Visit the bustling Mower's Saturday Market

Editor's Note: Photo taken from the establishment's official social account

Mower’s Saturday Market in Woodstock has been part of this small town’s history. This family-owned and operated market has been running for over 40 years. On weekdays, the grass-covered field in Maple Lane is unused. On Saturdays and Sundays, the vacant space is full of stands laden with in-season fruits and vegetables, fresh eggs from the surrounding farms, housewares, accessories, and even live chickens and ducks for sale.

The sound of sellers urging people to buy their products and buyers haggling with the vendors turns the quiet space into a cacophony of sounds. The scene is exciting to watch. You can also apply to be a vendor for a minimum fee. Mower’s Saturday Market is open every weekend from May to November.

Mower's Saturday Marrket

Address: 11 Maple Ln, Woodstock, NY 12498, United States

Website: Mower’s Saturday Market

6. Visit the historic Karma Triyana Dharmachakra Tibetan Buddhist Monastery

Editor's Note: Photo taken from the establishment's official social account

This Buddhist monastery in the charming town of Woodstock is always worth a visit. The atmosphere exudes a spiritual vibe, allowing you to reflect and meditate. Visitors are welcome to explore the place and enjoy the serenity and solitude that bring total relaxation.

There is a gift shop where one can buy some souvenirs and other items. For visitors who love hiking, there are two trailheads for a short hike. You can also join retreats to learn more about Buddist teachings, and free weekly classes are available too.

Karma Triyana Dharmachakra Tibetan Buddhist Monastery

Address:335 Meads Mountain Rd, Woodstock, NY 12498, United States

Website: Karma Triyana Dharmachakra Tibetan Buddhis Monastery

Opening hours: 9am - 5pm (daily)

7. Shop at Tinker Street

Tinker Street is the main street of Woodstock. This area used to have head shops that drew hippies. Today, it is one of the best shopping areas in the Catskills. It also features budding musicians who play instruments during warmer months.

Shops selling various items line the street, displaying clothes, accessories, cosmetics, wines, paintings, and a lot more. People flock to this street to window shop, and if their budget allows, buy something at a great bargain.

Tinker Street

Address: Tinker St, Woodstock, NY 12498, United States

8. Hike the Overlook Mountain

Overlook Mountain is part of the Catskill Mountains. The hike is easy and short, featuring a few steep parts. Climbing Overlook Mountain is an interesting experience because it features old structures that have been part of history.

You will pass by the ruins of what used to be a resort called Overlook Mountain House. Close to the summit is an old tower where fire watchers used to stay during summer. The overlook is a ledge where you can stand and see the view of the Catskills and the Hudson River. Marvel at the stunning panorama and enjoy the refreshing mountain breeze. The hike is quite tiring, but it is definitely worth your time and effort.

Overlook Mountain

Address: Catskill Mountains, New York, United States

9. Eat organic sourdough at Bread Alone

Editor's Note: Photo taken from the establishment's official social account

Bread Alone has been serving Woodstock for 20 years already. Its most popular product is the selection of sourdough bread made of organic stone-ground flour, organic grains, water, and sea salt. It is also known for its Nordic bread. Made of nuts, seeds, grains, and eggs, these loaves are very delicious and nutritious. The bakery also sells different kinds of rolls, bagels, and other pastries.

Today, Bread Alone has dine-in services for breakfast, lunch, and dinner. Customers can opt for takeout or dine in, too. A few tables and chairs have been added to accommodate its fast-growing number of patrons.

Bread Alone

Address: 22 Mill Hill Rd, Woodstock, NY 12498, United States

Website: Bread Alone

Opening hours: 7am - 5pm (daily)

10. Enjoy live music at the historical Colony Woodstock

Editor's Note: Photo taken from the establishment's official social account

Enjoy live music at Colony Woodstock, a historical hotel-turned-theater that dates to 1929. Today, it welcomes musicians and performers in the great room. Meals and drinks are served during the show.

If one wants to get fresh air, they have Beer Garden—an open space with picnic tables and a separate stage. Guests who wish to practice their singing prowess can do so every Monday during open mike sessions.

Woodstock Colony

Address: 22 Rock City Rd, Woodstock, NY 12498, United States

Website: Woodstock Colony

Opening hours: Mon & Wed - Fri: 6pm - 11pm; Sat - Sun: 11am - 11pm (closed on Tue)

11. Watch a movie at Woodstock Film Festival

Editor's Note: Photo taken from the establishment's official social account

Every fall, people from near and far come to town to watch movies at the Woodstock Film Festival. This annual event showcases independent and high-quality films. The participants come from almost all corners of the world — from as far as Siberia to the Hudson Valley itself.

There are animations, short videos, music videos, movies, and more. Big names in the movie industry also attend the event. Rub shoulders with famous actors, actresses, and other celebrities if you see them. Between festivals, the organizers also open workshops and other events for filmmakers.

Woodstock Film Festival

Address: 13 Rock City Rd Woodstock, NY 12498, United States

Website: Woodstock Film Festival

12. Relish Italian cuisine at Cucina Woodstock

Editor's Note: Photo taken from the establishment's official social account

Cucina Woodstock is one of the most popular restaurants in town, known for its contemporary Italian cuisine. Opened by Chef Gianni Scappin and Lois Freedman in 2006, this stylish restaurant in a renovated farmhouse offers dishes made from seasonal and fresh ingredients. Gluten-free pasta and pizza are also available.

Enjoy a candlelight dinner at the wraparound porch, where you can enjoy the cool night breeze. Families can reserve the 24-seater communal table or have a private dinner in the dining room. The ambiance is great, and so is the food. Take-out is available.

Cucina Woodstock

Address: 109 Mill Hill Rd, Woodstock, NY 12498, United States

Website: Cucina Woodstock

Opening hours: Sun - Thu: 5pm - 9:30pm; Fri - Sat: 4pm - 10pm

13. Savor Middle Eastern appetizers at Joshua's Cafe

Editor's Note: Photo taken from the establishment's official social account

Dine at Joshua’s Cafe and savor Middle-Eastern-inspired dishes lovingly prepared by the owner and chef Stefanie Schachter. The restaurant serves dishes to suit all kinds of lifestyles - vegan, vegetarian, gluten-free, and paleo.

Established in 1972, Joshua’s Cafe is a favorite among locals. They source fresh and seasonal ingredients as close as possible, and they also offer craft beers from the New York state. Reservations are welcome, too.

Joshua's Cafe

Address: 51 Tinker St, Woodstock, NY 12498, United States

Website: Joshua’s Cafe

Opening hours: Thu & Sun: 12pm - 8pm; Fri - Sat: 12pm- 9pm (closed Mon - Wed)

14. Watch a play at Woodstock Playhouse

Editor's Note: Photo taken from the establishment's official social account

Woodstock Playhouse is not only a landmark but also part of American Theater History. Built in the late 1930s, this theater is part of the Hudson River Valley National Heritage Area. It has been the venue for different types of productions and international performances. It is owned and directed by the Pan American Dance Foundation and the New York Conservatory for the Arts of Hurley, New York.

Today, visitors can watch a wide array of performances at the theater that include international festivals and events. Catch shows from the Woodstock Symphony Orchestra, Woodstock Playhouse Productions, and more.

Woodstock Playhouse

Address: 103 Mill Hill Road, Woodstock, NY 12498, United States

Website: Woodstock Playhouse

15. Catch a live performance at Harmony Music Woodstock

Editor's Note: Photo taken from the establishment's official social account

Catch a live show at Harmony Music Woodstock, where you can watch energetic performances and listen to all types of music by famous bands and musicians. Harmony is the place for music lovers and people who love to dance to the rhythm.

Watch out for weekly show updates to make sure you do not miss your favorite performers and their exciting numbers. You can also have a refreshing bottle of beer or a glass of wine while enjoying the performance.

Harmony Music Woodstock

Address: 52 Mill Hill Rd, Woodstock, NY 12498, United States

16. Relish homemade ice cream at Taco Juan's

Taco Juan’s is a Mexican restaurant that has been serving Woodstock for over 35 years. They serve burritos, tacos, salads, and appetizers. All ingredients are fresh, and the dishes are lovingly prepared.

Cap your delicious meal with Taco Juan’s homemade ice cream and sorbet, a favorite of residents and visitors of Woodstock.

Taco Juan's

Address: 31 Tinker St Woodstock, NY 12498, United States

Opening hours: 11am - 5:30pm (daily)

17. Tour the sculpture garden of Woodstock School of Art

Editor's Note: Photo taken from the establishment's official social account

Woodstock School of Art offers year-round classes in drawing, painting, and sculpture making, and they welcome artists of all skill levels and experiences. Studio rentals are also possible.

The sculpture garden of Woodstock School of Art has been the product of the artistic skills and toils of several members of the school’s residents. Using blue stones abundant in the area, they stacked these objects to form several outstanding works of art. Standing among green vegetation, these sculptures seem to guard the garden against invaders.

Sculpture Garden of Woodstock School of Art

Address: 2470 Route 212, Woodstock, NY 12498, United States

Website: Woodstock School of Art

Opening hours: Mon - Fri: 9am - 3pm; Sat: 9am - 1pm (closed on Sun)

18. Take a stroll around Thorn Preserve

Editor's Note: Photo taken from the establishment's official social account

Stroll around the Thorn Preserve and enjoy the best views of Overlook Mountain. This nature preserve boasts 60 acres (24.3 hectares) of sweeping grasslands, ponds, wetlands, and forests along the riverbank. It serves as the perfect habitat for birds, butterflies, bees, and other pollinators.

This area is maintained by Catskill Center. There are walking paths available, but most of the preserve is kept undeveloped for educational and agricultural purposes. The views also serve as an inspiration to artists.

Thorn Preserve

Address: 55 John Joy Rd, Woodstock, NY 12498, United States

Website: Thorn Preserve

Opening hours: 8am - 8pm (daily)

19. Have a taste of organic meals at Sunfrost Farms

Editor's Note: There's no photo available at the time of writing

Enjoy yummy chicken fajitas and other vegan and organic dishes at Sunfrost Farm in Tinker Street. This restaurant is a haven for vegetarians and vegans. Savor the fresh vegetables and skinless chicken breast wrapped in a thin corn tortilla. Feel refreshed after drinking smoothies and juices, which are made from the freshest fruits on the farm.

Ask for Today’s Specials for a treat and order your lunch online. You can also buy fresh produce in retail and wholesale.

Sunfrost Farm

Address: 217 Tinker St, Woodstock, NY 12498, United States

Website: Sunfrost Farms

Opening hours: 9am - 5pm (daily)

20. Have fun at Village Green

Editor's Note: There's no photo available at the time of writing

Village Green is a park and a gathering place for artists that made Woodstock their home. You can sit on a bench and watch people paint, make crafts, play musical instruments, and even hear popular singers ender a song.

Today, Village Green also serves as a venue for concerts and other events, such as the annual Woodstock Concerts on the Green every summer. When there are no events, one can just sit, enjoy the peaceful ambiance, and watch people go by.

Village Green

Address: 6 Tinker St, Woodstock, NY 12498, United States

Opening hours: 6am - 8pm (daily)

Discover art, music, and nature in Woodstock

Woodstock is a haven for art and music lovers, as well as those who like to commune with nature. Watch movies and live performances, go hiking, or relish the various cuisines that this town offers. No matter the season, you will find endless things to do in Woodstock, New York.