Location: Ossining, N.Y.
Year opened: 1825
Inmate population: 1,533
Facts: The phrase "up the river" refers to prisoners being sent up the Hudson River from New York to Sing Sing prison. The prison is closely associated with the electric chair, and between 1890 and 1963, 613 men and women were executed by this method. In 1953, Julius and Ethel Rosenberg were put to death at Sing Sing for espionage during the Cold War.