Ossining may refer to:

• Ossining, New York, a town in Westchester County, New York state
• Ossining (village), New York, a village in the town of Ossining
• Ossining High School, a comprehensive public high school in Ossining village
• Ossining Electric Railway, a former streetcar transit line in Westchester County
• Ossining station, a commuter rail stop on the Metro-North Railroad's Hudson Line in Ossining village
• "Ossining", a 2003 song by Mike Doughty from Rockity Roll

• Sing Sing, a New York state prison located in Ossining