Nestled In New York's Catskill Mountains Is A Quirky, Artsy Town Full Of Farm-Fresh Food And Cozy Charm

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.

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.

If music isn't your thing, there is no need to worry; Woodstock has plenty else on offer. From delicious food and shops filled with quirky goods to a charming main street and scenic views, your stay will be filled to the brim. Start your day by heading to the Village Green park on Tinker Street, and you might stumble upon an extravaganza. Various outdoor events take place there throughout the year, including a community drum circle and dancing. 

From there, wander down streets filled with stores housing unique jewelry, charming clothing, and contemporary art. When you're tired from all of the walking and shopping, stop into one of the restaurants lining the village streets for some grub, like Tinker Taco for tacos made with fresh tortillas and local ingredients or Silvia for New American cuisine made with locally sourced goods and organic vegetables.

If you visit Woodstock in the late spring through early fall, pick up some locally-grown and locally-made items at the Mower's Saturday Sunday Flea Market, held every weekend just a couple of blocks away from Village Green. Vendors sell antiques, produce, vintage clothing, jewelry, ready-to-eat food, and more. Once you've gotten your fill of shopping and eating, take a moment to take in the full beauty of being in the Catskill Mountains, known for their unique waterfalls and gorgeous views. Head to hike Overlook Mountain, less than a 10-minute drive from Woodstock's Village Green, and hike the 5-mile roundtrip trail for a stunning view from the top.