The 411: Ossining has roots that stretch back to 1685, when Dutch immigrant Frederick Philipse bought a large tract of land that included what would become modern Ossining. It was known as Sing Sing—a name derived from a local Native American word—from 1813 until 1901, when it was changed to differentiate the surrounding area from the maximum-security prison it had become synonymous with. The Town of Ossining comprises two villages: the Village of Ossining and part of Briarcliff Manor, the rest of which is part of the Town of Mount Pleasant.
One of the county’s Rivertowns, Ossining is perched on a strand of hills overlooking the Hudson, affording, on clear days,views of the Manhattan skyline. The town retains much of its original character and boasts a myriad of historic sites. Single-family homes comprise the majority of the town’s housing options. Outdoor enthusiasts revel in the town’s Cedar Lane Park, Teatown Reservation, and three boating clubs.