For those looking for a cozy escape in New York, there are plenty of charming towns scattered throughout the Empire State, and Woodstock goes above and beyond by leaving anyone who visits feeling full of inspiration and creativity. Settled in the Catskill Mountains, the beloved town is known for its lively art community and vibrant music scene, as well as for inspiring the name of the iconic Woodstock Music and Art Fair. The festival is internationally famous, but the town remains a hidden gem.
Fans of the festival’s musical legacy will still find plenty to appreciate about the music scene in the town in the 21st century, and the cozy vibes of the area and the farm-fresh food available don’t hurt either. Getting to town is a quick two-hour drive from New York City, and Trailways offers a bus service for those without a car and who don’t want to rent one. Once there, the heart of Woodstock is walkable and provides a lovely setting to get those steps in.
Fun for music lovers in Woodstock, New York
Housing one of the country’s oldest arts colonies, the town of Woodstock has long been recognized as a premiere creative destination. The 300-acre Byrdcliffe Arts Colony began fully operating in 1903 and still holds year-round events over a century later. Over the years, a slew of well-respected artists have visited and lived in the area. Author Thomas Mann, painter George Bellows, poet Wallace Stevens, and actor Chevy Chase are among the beloved names on that list.
Bob Dylan — who lived in an apartment on the popular Tinker Street — is also part of that distinguished group. The iconic singer-songwriter spent his days there crafting songs in a small apartment, as well as in the since-shuttered Café Espresso below the residence. Despite being a staple in town, Dylan didn’t take part in the famous August 1969 festival of the same name, which was actually held about 60 miles outside Woodstock on a massive dairy farm in Bethel, New York. Supposedly, the Bard didn’t even attend the event, missing out on a long list of performers like The Grateful Dead, Santana, The Who, and Jimi Hendrix.
After celebrating the town’s musical past at Dylan’s old stomping grounds of Tinker Street or attending a Byrdcliffe exhibit, embrace a new generation of Woodstock artists by taking in some live music. You don’t have to travel south to New York City for live music, as venues like Bearsville Theater, Colony, and Maverick Concert Hall offer something for everyone, no matter what genre of music you prefer.
Where to eat and shop in Woodstock
