10 Best Things to Do in Woodstock, New York

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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.

© 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

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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.

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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. Read more

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

© 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

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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

© 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

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The River Rock Health Spa is a luxurious spa and wellness center in the heart of Woodstock that provides a tranquil escape from the hustle and bustle of the city. The resort features a broad range of spa services offered by New York State licensed professionals, including massages, skin care treatments, waxing, pedicure and manicure services, melt method classes, and alternative wellness options.

Alternative wellness treatments include aura photography, hand analysis, and intuitive kinesiology, while luxury treatment products include premier brands such as Aveda and Eminence Organic Skincare. A variety of spa packages are available, and they include a combination of aromatherapy, massages, treatments, catered lunch, and goodie bags, and the River Rock Health Spa Art Gallery features artworks from regional artists that are available for purchase.

62 Ricks Road, Woodstock, New York, Phone: 845-679-7800

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© Bread Alone

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