Woodstock, NY
A historic walking village and the heart of the area's music and arts scene. Dylan lived right in town (in what's now the Espresso Cafe), and it's full of galleries, shops, hikes, and summer outdoor music.
Things to Do
Overlook Mountain
A steep but rewarding hike right over town, with hotel ruins and a fire tower and huge views up top. website ↗
Comeau Property
An easy in-town trail across from town hall, doable with younger kids.
Mower’s Flea Market
A big, beloved weekend flea market in the warmer months. website ↗
Dining
Tinker Taco Lab
Surprisingly great tacos.
Lodging
Woodstock Way
High-end, full-service cabins right in the middle of town. website ↗
Hotel Dylan
Funky and fun, with a pool, a five-minute drive from the center and across from the reservoir. website ↗
Live Music
Colony
A 1929 landmark on Rock City Road, restored into Woodstock's rowdiest little music hall — indoor stage, a back Garden, and the Patio for early sets.
Bearsville Theater
Built as part of Albert Grossman's Bearsville complex, this 16-acre spread on Tinker Street has hosted the Hudson Valley's favorite touring acts for decades.
Levon Helm Studios
'The Barn' on Plochmann Lane — Levon Helm's home studio and the birthplace of the Midnight Ramble, still one of the most intimate rooms in America.
Maverick Concerts
America's oldest continuous summer chamber-music festival, in a hand-built wooden hall in the woods since 1916. Jazz, family Saturdays, and Friday nights too.
Pearl Moon
A family-run restaurant, bar, and music room on Mill Hill Road serving dinner shows, brunch sets, and late-night grooves.
Woodstock Playhouse
A summer-theatre landmark at the gateway to Woodstock since 1938 — Broadway-style musicals, concerts, and the Woodstock Fingerstyle Guitar Festival.