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Get to know Ossining

Steeped in pre-Revolution history and brimming with period buildings spanning the course of four centuries, the town once called “Sing Sing” is an anything-but-sleepy place. Scenic Ossining manages a unique balance between modern practicality, like the mid-rise apartments by the revitalized riverfront park, and the pastoral foundation on which the town emerged, characterized by its hopping downtown and storied neighborhoods like Crotonville. Metro-North can shuttle you to the city in 45-70 minutes, depending on train, or whisk you northward to a mountain hike. A handful of private boating clubs are matched by public canoe and kayak launches along the historic Hudson’s banks, where waterside dining pairs with perfect sunsets. The town also teeters on Teatown Lake Reservation, an enchanting thousand-acre’s wood of natural terrain that includes a lily pad-patterned lake and enchanting Wildflower Island, a conservation effort for native flora.

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Living in Westchester

Don’t call it upstate. This cosmopolitan county north of New York City is a collective of towns, hamlets and mid-sized cities that put virtually every lifestyle imaginable within an hour’s commute of Manhattan. It’s due north of the Bronx, next door to Connecticut, and the gateway to the Hudson Valley. Metro-North’s Harlem, Hudson and New Haven lines make for speedy service into Grand Central — an express ride from many down-county communities runs comparable to the F train from South Brooklyn, with a much sunnier view. Lower Westchester’s villages prioritize convenience, while the verdant horse country to the north is a favored destination for those looking to fade away in privacy. The Hudson and Long Island Sound form its two coasts, conspiring with an inland chain of lakes and reservoirs for unbeatable boating, fishing and other recreational endeavors. Chain stores are noticeably absent from many Main Streets, which run chockablock with character-filled indie shops.