10 Best Things to Do in Woodstock, New York

By VacationIdea Staff on October 25, 2022 - Updated

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Located in the heart of the Catskill Forest Preserve, Woodstock, New York, has an active artist’s community and hosts local art festivals like the famous Woodstock Film Festival, which attracts artists and musicians from all over the world. This welcoming little village boasts a range of comfortable accommodations, excellent restaurants, museums, the Mower's Saturday Market, and a beautiful Buddhist monastery. Here are the best things to do in Woodstock, NY.

We recommend that you call the attractions and restaurants ahead of your visit to confirm current opening times.

1.Overlook Mountain

Taking center stage in the magnificent Overlook Mountain Wild Forest region of Catskill Park, Overlook Mountain is the southernmost peak of the Catskill Mountains and the site of one of the five remaining Catskill Mountain fire towers and the Overlook Mountain House hotel. Designed by Lewis B. Wagonen in 1871, the hotel gained fame for being built at a higher elevation than any of the nearby hotels. It later burned down, and the ruins can be visited from one of the main hiking trails in the park.

The Catskill Mountain fire towers were constructed to prevent and control forest fires in the region between 1908 and 1950. The twenty-three towers fell into disuse two decades later, but five of the towers have been restored and reopened for public observation. Visitors can explore the region on a 9-mile hiking trail that winds around the mountain from Fire Town to Echo Lake and includes the Ledges.

More weekend & day trip ideas: 15 Best Things to Do in New Paltz, New York.

2.Karma Triyana Dharmachakra Tibetan Buddhist Monastery

Founded in 1976 by the 16th Gyalwa Karmapa, Karma Triyana Dharmachakra is a Tibetan Buddhist Monastery located in the heart of the Catskills Mountains just above Woodstock. The monastery offers a range of Dharma teaching workshops and classes and several practice retreats in the tradition of Tibetan Buddhism. The monastery also provides two tours each week for visitors from around the world.

Weekend programs about the Buddha's teachings on wisdom and compassion are held every weekend and include workshops on Tibetan language and music and instruction in advanced Tibetan Buddhist (Vajrayana) practices.

335 Meads Mountain Rd, Woodstock, New York, Phone: 845-679-5906

3.Things to Do in Woodstock, New York: Shawangunk Mountains

The Shawangunk Mountains, also known as the Shawangunk Ridge or the Gunks, are comprised of a ridge of bedrock that spans from the northernmost point of New Jersey to the Catskill Mountains through Ulster, Sullivan, and Orange Counties. Once used for mining, logging, and huckleberry picking, the ridge is today a popular outdoor recreation venue for mountain climbers, hikers, mountain bikers, and wildlife enthusiasts.

Most of the northern Ridge is protected by the Minnewaska State Park Preserve and Sam’s Point Preserve and boasts more than 100 miles (160 km) of hiking trails, including the Long Path long-distance, several old carriage trails, and a number of climbing areas. Teeming with rich biodiversity and breath-taking scenery, the Ridge has been designated as a Nature Conservancy area and offers a range of conservation programs for the public.

4.Mower's Saturday Market, Woodstock, NY

Mower's Saturday Market is a traditional family-owned and operated market held every Saturday and Sunday in a grass-covered field down Maple Lane. Celebrating its 38th continuous season and serving as a vital part of Woodstock's tradition, Mower's Saturday Market is situated on two beautiful acres in the heart of Woodstock and features a variety of stalls. If you are wondering what to do in Woodstock, this is a great place to visit.

Vendors sell farm fresh products, fruits and vegetables, handmade goods and clothing, artworks, baked goods, furniture, antiques, collectibles, jewelry, and fresh flowers. Visitors can discover the town of Woodstock on a fun Woodstock Town Tour, which explores the lovely little town and all it has to offer.

Maple Lane, Woodstock, New York, Phone: 845-679-6744

5.Things to Do in Woodstock, New York: Cucina Woodstock

Tucked away in a beautifully restored rambling farmhouse in historic Woodstock, Cucina is a rustic Italian restaurant owned by Chef Gianni Scappin and Lois Freedman. Radiating a warm and welcoming ambiance in a country chic setting, Cucina presents a menu of contemporary Italian cuisine made with seasonal locally sourced ingredients that can be enjoyed at a large communal table with friends or in the private dining room.

A large wraparound porch is perfect for alfresco dining in the summer, while a crackling fireplace beckons on cold winter nights when diners can enjoy hearty dishes such as pork saltimbocca and prosciutto served with baked polenta and grilled lamb chops with olive tapenade. Adjacent to the restaurant is The Barn, a lovely restored 19th-century barn that can be rented for special events, weddings, and celebrations.

109 Mill Hill Rd., Woodstock, New York, Phone: 845-679-9800

6.Bearsville Theater, Woodstock, NY

Perched on the Sawkill Creek in a picturesque streamside setting, the Bearsville Theater is the brainchild of music industry visionary and magnate, Albert Grossman and presents an array of outstanding theater to the community of Woodstock. Opened in 1989 by Albert’s widow Sally Grossman, the theater’s stage has been graced by several famous celebrities, including Paul Newman, Jimmy Cliff, and The Pretenders, among others, as well as several talented local artists.

The theater property is also home to two restaurants – The Little Bear and the renowned Bear Café – and the offices of Radio Woodstock and WDST. The theater can be rented for special occasions and celebrations, providing a one-of-a-kind venue for an array of musical, theatrical, catering, and special events.

291 Tinker St, Woodstock, New York, Phone: 845-679-4406

7.Things to Do in Woodstock, New York: Sunfrost Farm

Sunfrost Farm is the Hudson Valley's leading retailer of local and organic farmers, supplying a range of organic produce such as free-range eggs, naturally reared meat and poultry, and locally produced non-GMO dairy. Visitors to Sunfrost Farm can enjoy a variety of delicious home cooked cuisine for breakfast and lunch, ranging from fresh sandwiches, soups, and salads to melts, wraps, and specials such as chicken fajitas, the Turkey Reuben, and a stacked BLT.

Desserts include freshly baked cakes, muffins, pastries, and baklava while thick ice cream shakes and blended fruit shakes make for a sweet end to the meal.

217 Tinker St, Woodstock, New York, Phone: 845-679-6690

8.Catskill Center Thorn Preserve

The Thorn Preserve protects and showcases around 60 acres of scenic natural landscape close to Woodstock. Home to outstanding views of Outlook Mountain, the preserve boasts sweeping grassland habitats, forested areas and ponds. The preserve forms an appealing outdoor recreational area for locals as well as serving several conservation purposes. Within the preserve there is an on-going Save the Hemlocks Project as well as a sanctuary for honey bees. The public are encouraged to use the mowed pathways to explore this very scenic and peaceful preserve on foot and to stop a while and enjoy some nature observation and bird-watching.

Catskill Center Thorn Preserve, 55 845 586 2611

9.Bread Alone, Woodstock, NY

Located in the center of Woodstock, Bread Alone is a family-owned bakery that has been serving organic bread, pastries, and café foods since 1983. Using only the best organic grains and wood-fired brick ovens, Bread Alone produces a variety of bread, including French sourdough, peasant bread, and nine mixed grain bread as well as European-inspired pastries such as croissants, scones, tarts, and Danishes.

Bread Alone also offers a casual café menu of seasonal dishes from the Hudson Valley, ranging from healthy and hot breakfasts of tacos caseros, sourdough French toast and oatmeal, and light lunches of fresh sandwiches, soups, salads, and the homemade quiche of the day. Hot and cold beverages range from coffee, tea, and hot chocolate to soda, seltzer, and lemonade.

22 Mill Road, Woodstock, New York, Phone: 845-679-2108

10.Levon Helm Studios

Continuing the decades-old rock ‘n roll traditions of Levon Helm, one of one of Americas most outstanding drummers, the Levon Helm Studios are housed in a beautiful barn in the heart of Woodstock. The barn was designed and acoustically engineered by the legend himself in 1975 and was built using local hemlock, pine and bluestone. Once the meeting and jamming place of countless rock ‘n roll legends, the Levon Helm Studios once again bring the music to Woodstock, staging regular intimate shows in the barn. Visitors who would like to attend one of the shows at the studio are requested to book online. Outside of show times the studio is closed to the public.

Levon Helm Studios, 160 Plochmann Lane, Woodstock, NY 12498, 845 679 2744

11.Maverick Concerts

Maverick Concerts has been producing summer chamber music festivals for more than 100 years, making it the longest running festival of its kind in America. The festival runs for about 4 months each year (June to September) treating locals and visitors to some excellent music by renowned ensembles and soloists every Sunday afternoon. In recent years, there has been a shift towards more contemporary music and many young artists are encouraged to join in. The concerts take place in a really magical setting in the heart of a forest. The all-wood “concert hall” dates back to 1916 and is recorded on the National Register of Historic Places.

Maverick Concerts, 120 Maverick Rd, Woodstock, NY 12498, 845 241 7721

12.Woodstock Playhouse

No visit to Woodstock would be complete without attending a show at the famous Woodstock Playhouse, which was established back in 1938. Many of today’s celebrated Broadway and off-Broadway performers cut their teeth at the Woodstock Playhouse and the theatre also features brilliant performers from all over the country. Performances include concerts by the Woodstock Symphony Orchestra, the Rock Academy students, and the core performers of the Summer Stock Season. The summer concert series runs from June through August and attracts many theatre-lovers from all over New York State and beyond. Check their website to see what’s on during your visit.

Woodstock Playhouse, 103 Mill Hill Rd, Woodstock, NY 12498, 845 679 6900