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Sing Sing in Ossining (8/31/26)

Bob and I had a unique 1.5 hour tour today about the American penal system and Sing Sing Correctional Facility in particular. A Sing Sing Prison Museum is being built, but in the meantime, they are offering theses tours in Louis Engel Park along the banks of the Hudson River and next to where the Sing Sing Correctional Facility is located.

While there is much to be improved with the American justice system and prison experience, and we were asked specific questions about our views on the purpose of prisons, etc. during the outside walking tour, I won’t go into that portion of the tour but just share the very few facts that we learned about Sing Sing.

First, Sing Sing is a maximum security facility with a capacity of 1,600 men. It is located in Ossining, NY, about 6 miles north of Tarrytown. It is the only prison that has a trainline running through it. It was built by convicts beginning in 1825 and completed in 1827 using marble (now called Sing Sing marble) quarried from the site. The new prison was needed as prisons in New York City were no longer adequate and it was too cost prohibitive to build in the city.

The name Sing Sing comes from the mishearing of the Native American term for the area, Sinck Sinck, meaning stone upon stone. Originally, the name for the prison was Mount Pleasant and the town that grew up around it was called Sing Sing, but eventually, people decided that Mount Pleasant was a poor name for a prison, so they renamed the prison Sing Sing as well. The town wasn’t happy being known by the same name as the prison and renamed the town Ossining in 1901 as another variation of the Native American term for the area, Sint Sinks.

Before the tour, we were able to take photos of the lovely park area that we walked around. We were only able to go near not on the prison grounds and could only take a couple of quick photos at that location.

The yellow sign for our tour which began
near the boat and canoe rental facility in Louis Engel Park.
A pretty restaurant and residences just north of the park area where we had our tour
“River Arch” by Peter Lundberg, 2016
More landscaping, art, and residences along the riverfront
The boat and canoe rental building
Looking south at all the ducks by the rental boats
A small band stage in the park
A colorful mural on the public restroom in the park
A memorial stone for 9/11
Looking across the prison field
to the new prison housing facilities on the hill
The buildings at the end of the field are no longer in use.
The white brick building is the shell (no longer has a roof)
of the original dormitory, and the red brick building beside it was a gym provided by the former head of Warner Brothers Studios.

Apparently there was an agreement with Warner Brothers that allowed them some use of the prison for films. The tour guides made a point of saying at the beginning of the tour that they would not be discussing any specific prisoners or media related to the prison, although one guide mentioned a Bugs Bunny episode about Sing Sing and they offered up this little tidbit about the Warner Brothers executive. Bob and I wouldn’t have minded hearing more specifics about the prison, including those kind of stories, but they were more focused on getting people to really think about the prison system and how it functions in our society.

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