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Hudson Valley

Rhinebeck

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. 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.
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Hudson Valley

Red Hook/Tivoli

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