1. Woodstock, NY
Though the name conjures a crowd splashed in tie-dye and the faint scent of marijuana, Woodstock isn’t actually where the 1969 festival was held. (That was in Bethel, about two hours away.) Even so, the town is a mix of retired hippies—a street there is named after the late great Band member Levon Helm—artists and city dwellers who feel the need to flee the metropolis on weekends.
What to do: A hiking trail on Overlook Mountain leads to the Instagram-worthy remnants of an unfinished luxury hotel and views of Echo Lake. The General Store of Catskill (356 Main St, Catskill; 518-653-9188, catskillmtncountrystore.com) is another draw, located on the town’s historic Main Street and offering an array of locally-made bath, body and wellness products. Besides all the camping? If you’ve grown tired of that smoky campfire smell and yearn for a real table and chairs, pop into Oriole 9 (17 Tinker St; 845-OR9-5763, oriole9.com) in town. This local favorite is a café-cum-art-gallery that serves fantastic all-day breakfast and lunch. (Go for the curried coconut tofu hash.)
Where to stay: Stay at Woodstock Way, a comfortable and contemporary retreat near the center of town right next to the Tannery Brook Waterfall. Or, trade in four walls and a ceiling for something a little more portable. Tentrr.com is a campsite service available in Woodstock and elsewhere upstate. The idea is simple: Book a tent and arrive to a set-up campsite stocked with food and drink. It’s basically Airbnb for campers, touting fully-equipped campsites on private properties all across the Catskills. And don’t worry: Tentrr provides queen-size cots, because you’re too pretty to actually sleep on the ground.