Enjoy this content as part of Julia B. Fee Sotheby’s Inside The Community series.
Woodstock, New York, carries a deep-rooted legacy as a haven for creatives and innovators since the early 1900s. Its unique blend of artistic exploration and cultural breakthroughs has made it a cornerstone for those redefining art and music. Now, the town balances this rich heritage with a polished and thoughtful atmosphere, creating an inviting and distinctive escape.
Here’s what’s happening these days in Woodstock:
Dining
42 Mill Hill Road, Woodstock
Silvia reimagined the historic Joyous Lake music club as a modern New American restaurant, founded by a team of NYC transplants: Chef Doris Choi, her sister Betty Choi, Betty’s husband Niall Grant, and their partner Craig Leonard. At the heart of their kitchen is a commitment to clean and conscious cooking, with every dish made from scratch using non-GMO ingredients and a focus on sustainability and zero waste. Among the most talked-about dishes is the chicken schnitzel, served with silky mashed potatoes and tangy mustard jus. Another standout is the mushroom lentil pâté, a rich and earthy starter paired with pickled vegetables and charred sourdough that keeps guests coming back.
109 Mill Hill Road, Woodstock
Cucina is set in a lovingly restored 19th-century farmhouse just outside Woodstock’s village center, blending rustic charm with a modern Italian sensibility. The restaurant was created by seasoned restaurateurs Gianni Scappin and Lois Freedman, who envisioned a gathering place rooted in simple, seasonal cooking and warm hospitality. Signature dishes include the Caprina flatbread, layered with fig rosemary jam, goat cheese, mozzarella, pear, arugula, and a drizzle of truffle oil. The fusilli Bolognese with house-made ricotta is another favorite, offering a rich, comforting take on a classic.
Outdoor Recreation
Parking available at 335 Mead Mountains Road, Woodstock
Overlook Mountain Trail, just north of Woodstock, climbs about 1,400 feet over 2.3 miles along a marked historic carriage road. The path leads to the ruins of the 19th-century Overlook Mountain House and continues to a fire tower with sweeping views of the Catskills and Hudson Valley. The trail is moderately challenging but straightforward, suitable for families and dogs. From the top, the restored 60-foot fire tower offers stunning 360-degree views that make the climb worthwhile.
356 George Sickle Rd, Saugerties
Opus 40 is a stunning environmental sculpture created by Harvey Fite, set within a former bluestone quarry at the foot of Overlook Mountain in Saugerties, New York. Spanning 6.5 acres, it features thousands of tons of expertly crafted dry stone walls and is recognized as a pioneering work of Land Art. The site also includes 63 acres of meadows, trails, and historic buildings, preserved by Opus 40 Inc., founded by Fite’s wife. During the open season, Opus 40 presents a distinctive lineup of intimate concerts, immersive nature strolls, and skillful workshops, creating an inspiring space where art, history, and the landscape intertwine.
Local Favorites & Culture
22 Rock Street Road, Woodstock
Originally established in 1929 as the Colony Hotel, the venue was thoughtfully revitalized in 2017 by Neil and Alexia Howard, emerging as The Colony, a dynamic space dedicated to live performances and a warm, inviting atmosphere. Today, The Colony draws audiences with its intimate setting and an eclectic mix of local talent and acclaimed artists, offering something for every musical taste. Its rich history combined with a strong commitment to community and live entertainment has made The Colony a treasured gathering spot for both Woodstock residents and visitors seeking unforgettable experiences.
Tinker Street, Woodstock
Tinker Street serves as the sophisticated heart of Woodstock, where rich artistic heritage blends seamlessly with exclusive boutique shopping. Visitors can discover renowned establishments such as Three Turtle Doves, celebrated for its exquisite vintage pieces with Art Deco flair, Woodstock Trading Post, a longtime favorite for premium denim, and The Healing Shop, known for its detailed selection of spiritual and wellness goods. The street also features the esteemed Woodstock Artists Association & Museum, which presents a distinguished collection of regional art.