Sing Sing Prison, Ossining, NY: A History of Hudson Valley’s Jail Up the River

One of America’s most infamous prisons, Sing Sing has been housing criminals for nearly 200 years



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The natives who lived there called themselves the Sint Sink, which meant “stone upon stone.” The 17th-century Dutch interlopers appropriated their land and altered the name to Sinck Sinck or Cinque Singte. In the mid-1800s it became known as Ossin-sing, from another Native American word, ossin, also meaning stone.

But criminals have always called it “up the river.”

Sing Sing, the prison, and Ossining, the town, are inextricably linked. Indeed, in 1902 the town changed its name only because the prison had become so notorious. And that’s just one of a multitude of facts, stories, and myths surrounding this nearly 200-year-old star of stage, screen, song — and grisly executions.

Its age was one of the things that inspired Guy Cheli, a writer who lives in Mahopac, to research and write Sing Sing Prison, a book in the “Images of America” series published by Arcadia Publishing in 2003. “It was built in 1825, and there aren’t many things still standing now from 1825,” says Cheli, 58, a member of the Ossining Historical Society. Like many who work or live in the region, Cheli was aware of the prison but not its history. “It’s right there in Westchester County,” he says, “but I never really knew the story behind it.”

(Continued on next page)

» Visit Sing Sing Prison Visitor Center in Ossining, NY
» Visit Ossining Historical Society in Ossining, NY

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