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.