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 aerial viewThe prison sits on the banks of the Hudson, making escape more difficult

Photograph courtesy of Library of Congress Prints and Photographs Division

You dirty rat...

The name Sing Sing almost immediately conjures images of the gangster era of the 1920s and ’30s, of Jimmy Cagney movies and cops-and-robbers radio serials. During that time the prison housed the infamous Willie Sutton, Lucky Luciano, members of Murder Incorporated, and other well-known ne’er-do-wells. But by then, bad guys had been sent “up the river” from New York City courthouses for 100 years.

When New York State’s first two prisons — one in Greenwich Village dating from 1797 and the other in Auburn built in 1816 — became overcrowded, the Legislature commissioned Auburn Prison warden Elam Lynds to build a new and more modern prison. He decided to locate it in Mount Pleasant, near a small village called Sing Sing, because the stones implied by its name were still being quarried nearby.

In 1825, Lynds transferred 100 Auburn inmates by barge along the Erie Canal to freighters that took them down the Hudson to Sing Sing, where he forced them, at gunpoint, to build the new prison. It opened in 1826, and was fully built in 1828. The completed cell block was four tiers high. Each cell was seven feet deep, 39 inches wide, and about six-and-a-half feet high. But with crime a growth industry, it continued to expand for the rest of the 1800s. By the turn of the century, it housed more than 1,200 prisoners.

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

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