3 Clay Ct. Rhinebeck, NY 12572

We don’t know where Bob Dylan was headed when he wrote the song “Girl from the North Country,” but we’ve got a hunch that north country fair he sang of traveling to was Rhinebeck’s — it’s the state’s second-largest. The quintessential artsy upstate town, this storied community has long carried cachet in city circles. You might hear the gentle strum of a street musician’s guitar as you stroll its single-intersection shopping district, jam-packed with innovative eateries, avant-garde galleries, an art-house cinema, and purveyors of just about everything else from kitchen gadgets to cheeky letterpress cards. There’s no time more magical than the holidays when the streets are closed to welcome Sinterklaas in the old Dutch tradition, a spectacle witnessed from windows and rooftops. Tight-knit neighborhoods of cozy farmhouses and mansard-roofed Second Empires skirt the village, fading to farmsteads and old-money estates further out. Rhinecliff, the riverfront hamlet, hosts high-bluff views, marina slips, and the town’s Amtrak station.