Ossining High School (Downtown Ossining Historic District)

Ossining High School is a c.1929 Gothic Style building that anchors the southern end of the Downtown Ossining Historic District. It is a brick, three-and-one-half story building originally designed by James Gamble Rogers. Ossining High School possesses a tower and central cupola as part of its original structure, along with a modern three-story addition. A surviving example of pre-Great Depression architecture, it is included in the Downtown Ossining Historic District, which was placed on the National Register of Historic Places in 1989.

Named after the Sint Sinck Native Americans who inhabited the land until 1685. In 1693, the 52,500 acres were “transferred” from the Sint Sinck by royal charter to Frederick Philipse and became Philipse Manor. The Philipse family, who remained “Loyal” to the British during the American Revolution, had their property seized after war’s end in 1779, and in 1788 Sing Sing became part of the Town of Mount Pleasant. On April 2, 1813, the Village of Sing Sing became its own incorporated village in Westchester County, NY, the first municipality in the county to receive this designation. Eighty-eight years later, in 1901, the Village of Sing Sing changed its name to the Village of Ossining.

The Village is known for the Sing Sing Prison (known until 1851 as Mount Pleasant State Prison) that was constructed upon an abandoned marble quarry on the east bank of the Hudson River in1818. The Village of Ossining evolved to include a concentrated downtown area that became a commercial and social hub with many banks, churches, and thriving storefronts.

Ossining High School was built c.1929 to accommodate the growing student population in the village. It is a monumental three-and-one-half story stone and brick Collegiate Gothic style building with slate gable roof, and a tower and central cupola designed by James Gamble Rogers. The school includes a modern three-story addition. Ossining High School is included in the Downtown Ossining Historic District, which was placed on the National Register of Historic Places in 1989.

1. “Ossining Downtown Historic District #88001827.” National Register of Historic Places. United States Department of the Interior/National Park Service. Aug 9, 1989. https://catalog.archives.gov/id/75323005.  
2. “Ossining Downtown Historic District (Boundary Increase) #12001133.” National Register of Historic Places. United States Department of the Interior/National Park Service. Jan. 2, 2013. https://catalog.archives.gov/id/75323007.  
3. Williams, Gray. Picturing Our Past: National Register Sites in Westchester County. Westchester County Historical Society. 2003.