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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sing sing prison todayHard time: A modern-day view of the prison wall and watchtower

Rooms with no view

Today, Sing Sing houses about 2,000 inmates as a maximum-security prison. But it’s essentially hiding in plain sight. Its impact on the village has been minimal. “It has supplied jobs, but many of the workers don’t live locally anymore,” Cheli says. There have been only a handful of escapes. In 1980, prisoners held some guards hostage. “Most famously, in 1941, a village police officer and a corrections officer were shot and killed during a prison break,” Cheli says. The escapees were caught and executed.

The prison may come out of hiding, however, if plans for a museum and visitors center ever come to fruition. “In my opinion, that would be great,” Cheli enthuses. “The train from Times Square goes right past it. Imagine how many millions of people would go there — it could be like Alcatraz. It would be a boon for the village and the state.”

Cheli is biased, of course. “Sing Sing is my favorite subject that I ever covered,” he says. In fact, he has a personal collection of artifacts, including old books, photos, artwork, and letters from wardens and prisoners, some of it more than a century old. “I have a beaded necklace made by a prisoner in the late 1800s,” he says. “It looks like a Native American necklace.”

But his collection isn’t open for public viewing. As of now, only the Caputo Community Center in Ossining, which has a small exhibit, and the Ossining Historical Society — which is more library than museum — openly acknowledge the place where bad guys go when they are sent up the river.

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

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