The Town of Ossining includes the Villages of Ossining and Briarcliff Manor, and the unincorporated part of Ossining. Part of the 1685 land purchase by Frederick Philipse from the Sint Sinck Indains, Ossining was incorporated into the 52,000-acre Philipsburg Manor was settled by tenant farmers. After the Revolutionary War, the Philipse family lost their land and it was divided among those supporting the American cause. Around 1795, the settlement of Sparta started growing quickly (today, some of the old homes from that period are designated as historical district). Shortly after 1800, the newer community of Sing-Sing sprang up at Sparta. By 1813, Sing-Sing was a prosperous port where farm good were shipped to NYC. As a shipbuilding center, it also had the county's first newspaper, the Mount Pleasant Register, in 1791. Factories began to flourish in the late 1840's, including Brandreth's Pill & Porous Plaster, an iron foundry, a file works and a coton gin. Travelers found Ossining hospitable with its selection of  hotels and taverns. In 1813, Ossining became the first municipality to be incorporated in Westchester County. the building of Sing-Sing Prison was started in 1825; it remains in operation today. From 1891 until 1963, it was best known for its electric chair (614 inmates were put to death!). Perched above the Hudson River, Ossining's location affords some lovely views. Today Ossining provides a great variety of housing types and it's especially proud of its historic past (its slogan is "Old in history, new in spirit"). 
 

This is an excerpt taken from: "The Best of Westchester" by Marian Hamilton, Marken Publishing, Armonk, New York