Get to know Sleepy Hollow

If any legends are true here, it’s how the past of this charming commuter-friendly community blends so effortlessly with its present. Immortalized in Washington Irving’s classic tale, this Westchester river town—a village of Mount Pleasant, to be technical—was called North Tarrytown through 1996, when residents voted to reclaim its historic place name. While you won’t cross paths with a headless horseman stalking its foggy, lantern-lit streets, you’ll certainly stumble upon welcoming neighborhood haunts pouring local craft beer, along with miles of trails, an 17th-century Dutch church, and a stout coffee pot-looking lighthouse. The revitalized riverfront boasts a slew of sleek modern apartments, contrasting classic Colonials and mansard-roofed Second Empires on leafy lanes. Metro-North’s Hudson Line stops right at Philipse Manor, which surrounds the stately neighborhood of the same name.

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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.