65 Ricks Woodstock, NY 12498

In popular imagination, this Ulster County town seems inextricable from the 1969 concert sharing its name—which, truth be told, happened some 40 miles away. Woodstock: The place lies entirely within the boundaries of Catskill Park, surrounded by towering peaks and the Ashokan Reservoir, one of the largest and deepest serving the thirsty metropolis two hours south. This surreal landscape proved magnetic for musicians and artists alike, who founded the Byrdcliffe and Mavericks art colonies and helped root Woodstock as one of America's most storied (not to mention quirkiest) creative hubs. While peace, love, and drum circles are well at home here, you’d be best to shed your tie dye-tinged misconceptions. The downtown area is a modern tastemaker's mecca, brimming with specialty food shops, avant-garde galleries, and a Brooklyn-level restaurant and bar scene. Mountain trails, waterways, and the slopes of Hunter Mountain await with world-class wilderness recreation, making the region a popular escape for weekenders and full-time residents alike. The few everyday conveniences you won't be able to find are just down the road in nearby Kingston or Saugerties.