When Henry Hudson sailed his eponymous river, its shores were dense with wilderness—and while progress has since pruned space for al fresco dining and picket-fenced Victorians, Croton retains its wild roots. This five-square-mile community in the Town of Cortlandt sits ringed by woodland wonders. An abundance of trails fills Old Croton Aqueduct State Historic Park, and at Graff Sanctuary, you might hear the hoots of horned owls. Swimming holes in the hills ice over into skating spots in winter, and there’s even sandy beaches at Croton Point Park, home to the Clearwater Festival and a miniature airport for remote-control planes. But as boundless as its nature may be, it’s an intimate, friendly community. The quaint Upper Village stands guarded by a single landmark traffic light, one of few freestanding “dummies” still around, surrounded on all sides by swoon-worthy boutiques and the kind of hometown eateries that become part of the family. Croton-Harmon Station, served by Metro-North and Amtrak, links Manhattan, Albany and beyond.