Lower Hudson Valley
Ossining, New York
Village and town in Westchester County
A Hudson River village below Sing Sing's walls
Ossining is a village and town on the Hudson's east bank, known for the Sing Sing Correctional Facility, a historic downtown and a riverfront park. Its Metro-North station and relatively moderate prices make it a common entry point to the river villages.
History & Local Character
Ossining was settled in the 17th century and grew around Sing Sing prison, opened in 1826, and the railroad. The village incorporated in 1813 and retains a stock of 19th-century buildings.
Housing & Real Estate
The village mixes older houses, two-family homes, apartment buildings and some riverfront condominiums, with more affordable options than villages to the south.
Restaurants & Shopping
Main Street and Highland Avenue carry Italian, Latin American, Indian and American restaurants, with cafes and bakeries serving the downtown.
Schools & Education
Ossining Union Free School District serves the village and town, with a high school and several elementary schools.
Parks & Recreation
Nelson Sitting Park, Louis Engel Waterfront Park and the Old Croton Aqueduct Trail provide riverfront and trail access.
Transportation & Accessibility
Metro-North's Hudson Line stops in Ossining, with Route 9 and the Croton-Harmon yard to the north.
Local Businesses
Restaurants, shops, contractors, medical offices and the prison's workforce support the local economy, with a downtown revitalization effort underway.
No businesses are listed in Ossining yet. Add your business to be the first.
Nearby Attractions
- Louis Engel Waterfront Park
- Sing Sing Historic Prison Museum
- Old Croton Aqueduct Trail
- Croton Gorge Park
Advantages & Considerations
Advantages
- Relatively affordable river villages
- Hudson Line rail access
- Waterfront park and trail connections
Considerations
- Industrial and prison land uses along the river
- Older housing stock
- Limited upscale retail
Frequently Asked Questions
Is Ossining a village or a town?
Both: the Town of Ossining contains the Village of Ossining and the unincorporated area of Briarcliff Manor-adjacent neighborhoods.
Is Sing Sing in Ossining?
Yes. The Sing Sing Correctional Facility is in the Village of Ossining.