Woodstock has retained the funky vibe that made it famous in the 1960s. Spend an afternoon on the main drag, Tinker Street, browsing the boutiques and galleries—one of our favorite stops is the Woodstock Artists Association & Museum, where you’ll find exhibits dedicated to work by area artists. Check into the recently opened Hotel Dylan, a hip 11-room boutique with fun in-room extras like Crosley record players and an assortment of vinyl, beach reads and games like Trivial Pursuit. For dinner, head just up the road to Italian restaurant Cucina, a lively local favorite housed in a former farmhouse. After dark, cozy up in an Adirondack chair around one of the Dylan’s fire pits. The next day, get an early start and drive up Route 28 to Phoenicia for a breakfast of biscuits and gravy at the town’s well-loved diner. Work off your meal with a hike to Kaaterskill Falls, a picture perfect two-drop waterfall, then meander your way south, saving time to pop into some of the 14 wineries along the Shawangunk Wine Trail.