Location: Ossining, NY
Notable Residents: Charles "Lucky" Luciano
Amenities: Rehabilitation programs to allow prisoners the chance to earn degrees

Sing Sing got its name from the Native American tribe "Sinck Sinck" (or "Sint Sinck"), who the land was bought from in 1685. The maximum security prison is located 30 miles north of New York City on the Hudson's east bank—hence the phrase "up the river." The prison was opened in 1826, two years before it was truly completed, the third prison built by the state of New York. Sing Sing was viewed as a "model" prison because it generated revenue for the state. As the Auburn System was in place, complete silence was expected from prisoners. Brutal beatings awaited those who disobeyed.

The electric chair was used at Sing Sing until the Supreme Court decided in 1972 that its use was unconstitutional. Six-hundred-and-fourteen men and women were executed at Sing Sing. After '72, the chair was transported to Greenhaven Prison, but never used again. The prison was accredited in 1989 by the American Correctional Association, creating a new set of standards that every correctional facility would be forced to adhere to.

Educational programs such as Rehabilitation Through the Arts (RTA) were established, and Hudson Link for Higher Education in Prison was created to keep college education at Sing Sing in place via private funding.

These days, Sing Sing holds over 2,000 prisoners, and there plans to turn the original cell block into a museum. Last year, it was rumored that the real estate boom would lead to the prison being closed for good. No word on that.