Was Sing Sing the name of a place? I was reading a Civil War documentary which mentioned Sing Sing as if it were a town. If so, did the prison take it’s name from the town? And, what is the origin of this odd name? - Jinx
Just to add to Fear Itself’s link, the joke is that the village changed its name from Sing Sing to Ossining in order to differentiate itself from the prison. The prison, of course, has since been renamed “Ossining Correctional Institution.” They just can’t win!
I guess you gotta Sing Sing for your supper in Ossining, NY! 
- Jinx
I’m not absolutely sure, but I think this is where the phrase “going up the river” for going to jail came from too. The remains of the dock are still there that delivered the hapless criminals from NYC up the Hudson to Ossining. The prison’s a jumble of old red brick buildings and modern squat grey ones, with lots of razor wire, but it’s smaller than you would think. And across the tracks is a playground on the river. Take the Hudson River Line out of Grand Central and you’re there in about an hour.
Literally. The Hudson line passes right through the prison.