If there’s one town in the Hudson Valley whose reputation has long preceded it, it’s Woodstock. Lizzie Vann, owner of the Bearsville Theater, says that when she was growing up in England, she envisioned Woodstock as a magical place. “Today, there’s probably still one in ten people here with a strong connection to the arts. As a community, we accept the unusual, the passionate, and the curious.”
Woodstock has been famous for creativity and music for well over a century, ever since author Hervey White founded the Byrdcliffe and Maverick arts colonies in the early 1900s. Nestled at the base of the Catskills, the town of 6,000 continues to attract hippies—as well as individuals and families looking for a rural lifestyle with culture and activities.
Ryan Giuliani, a part-time resident since 2004 and owner of Woodstock Way hotel and Que lo Que restaurant, says, “An artistic lifestyle in the mountains is just spectacular. After living in the city, it’s nice to slow down a bit.”
But life in Woodstock is never too slow. “Almost any night you can find live music somewhere,” boasts town supervisor Bill McKenna. You can catch a show at The Colony, Levon Helm Studios, Maverick Concert Hall, or the historic Bearsville Theater—founded by prominent rock manager Albert Grossman, whose clients included The Band and Gordon Lightfoot. There’s also the Woodstock Playhouse which hosts the local Woodstock Symphony Orchestra and other performances; plus, the area is home to Radio Woodstock, which broadcasts a mix of rock, folk, and indie tunes out of a former church.
The spirit of community is strong here. Family of Woodstock, Inc. serves Ulster County residents by helping them find shelter and aiding victims of domestic violence; they always welcome new volunteers to help operate their crisis hotline. The annual Woodstock Film Festival puts out a call for help during their annual week of short film screenings and professional panels—their event this year begins on September 27. There are also opportunities to clean and maintain the nearby Sloane Gorge Preserve and Ashokan Rail Trails through the Woodstock Land Conservancy.
The town is a part of the Onteora Central School District, which has a B+ rating on niche.com. The elementary school is in downtown Woodstock, and the middle and high schools are in nearby Boiceville—a 15-minute commute.
The public library—part of the expansive Mid-Hudson Library System—is on Library Lane, but will be moving to Bearsville, a small hamlet of Woodstock, as soon as renovations on the new building are complete. It’s open Monday through Saturday, and offers classes and clubs for all ages—like yoga, Lego building, and children’s story time.
In addition to small food shops like Woodstock Meats and Cub Market, there are two larger grocery stores: Sunflower Market, specializing in organic and local items, and Hannaford supermarket in West Hurley.
The town comprises the intersection of Tinker Street, Rock City Road, and Mill Hill Road. In all three directions, you’ll find a variety of restaurants and shops. Moonrise Bagels specializes in stuffed bagels—think bacon, egg, and cheese or chicken parm. Que lo Que cooks up Caribbean-inspired dishes like empanadas and Dominican fried chicken. For an upscale meal, book a table at Silvia, which crafts contemporary American cuisine, or its Southeast Asian-inspired sister restaurant Good Night.
Locals can stock up at The Golden Notebook, a cozy bookstore that carries many local authors. Lovewild Design sells sustainable gifts and has a bath-and-body refill station. Candlestock—a beloved candle emporium established in 1970—offers a wide selection of scented candles, hand-dipped tapers, and recycled wax tealights.
A place once frequented by the likes of Bob Dylan and Janis Joplin, and world-famous for the festival that didn’t take place there, Woodstock remains deeply rooted in the arts. With pride, it continues to be a scenic haven for creatives and free thinkers—all are welcomed with open arms.