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.