Good for hippies at heart
2 hrs, 11mins by car
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. Woodstock the chance to connect with nature thanks to Overlook Mountain and its various trails as well as a healthy shopping scene with quaint local shops like Candlestock and the Golden Notebook and its weekend flea market, delicious food that can be found at places like Silvia and The Mud Cub and drinks at Station Bar & Curio.