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Known as Sing Sing throughout the 19th century—a phrase that originates from a local Native American word—this town was renamed in 1901 in order to differentiate the actual town from the maximum-security prison that had been given the same name. Dating back to as early as 1685, the Town of Ossining includes two separate villages: the Village of Ossining and a part of Briarcliff Manor. Located on a long stretch of hills, the town overlooks the Hudson River and residents are, on clear days, able to spot the Manhattan skyline on the horizon.

Beyond being home to the infamous Sing Sing maximum-security prison, the downtown area of Ossining is home to a multitude of historical buildings, including several banks, a village hall and a former post office. Furthermore, Ossining features several sites that are dear to outdoor enthusiasts, including Cedar Lane Park, Teatown Reservation and three boating clubs.