Inside the History of Ossining’s Sing Sing Prison

Adobe Stock/ josefkubes

Learn how Ossining’s Sing Sing Prison, one of America’s most iconic prisons, came into existence in Westchester County.

Westchester recommendations are objective, unbiased, and curated by the editorial team. If you buy something through our links, we may earn an affiliate commission at no cost to you.

Captain Elam Lynds, warden of Auburn State Prison in upstate New York, had searched hundreds of miles for an ideal new prison location. In May 1824, Captain Lynds found his spot in Mount Pleasant.

The New York State Legislature wanted a third state prison in addition to Newgate, built in Greenwich Village in 1797, and Auburn, erected in 1816. Lynds—a former Army captain, now prison warden, with thick arching eyebrows and a chin like a shovel—had hunted for possible locations in Staten Island, the Bronx, and Mount Pleasant.

- Advertisement -

The 130-acre site that he chose belonged to the small Westchester village of Sing Sing on the banks of the Hudson River. The town’s name came from the Native American phrase “Sint Sinks,” which roughly translates to “stone upon stone.” It was there that Captain Lynds would cull 100 inmates from Auburn to lay brick upon brick in order to build the era’s most modern, impressive maximum-security penitentiary.

The land sat on the Silver Mine Farm, an abandoned mining site, which offered abundant world-class marble that made prison-building on the Hudson easy and cheap. Large quarries already cut into the county’s shoreline. The New York State Legislature appropriated $20,100 to the project and, in October 1828, the Sing Sing Correctional Facility was officially opened. The fortress stretched four stories and measured 476 feet long by 44 feet wide. Each cell spanned just about 20 square feet.

Sing Sing immediately turned a rare profit and soon began accepting women in 1837. (That policy ended 40 years later.) Captain Lynds emerged as a Patton-esque figure in the correctional community. His “Auburn system,” which drove rehabilitation through hard work, community activity, and silent reflection, swept through American prisons. He demanded that inmates not “exchange a word with each other under any pretense whatever; not to communicate in writing. They must not sing, whistle, dance, run, jump, or do anything that has a tendency in the least degree to disturb the harmony.”

Convicts received a Bible, walked only in lockstep, and saw no visitors. Rations included two eggs per year and nearly no fresh produce. Any misstep was met with whippings and confinement, for the delinquent was an anonymous sinner. Only suicide and depression crept between the silences.

This puritanism, however, was wildly popular in the early 19th century. Temperance had become the great narrower of American life. Penal experts believed that Lynds’ “silent system” would restore piety and prevent re-offenses, one even recommending that the criminal “be literally buried from the world.” The jail’s physical form fortified function. Brick cellblocks and tall guard towers separated Sing Sing from greater Westchester. Prisoners worked 10-hour shifts isolated in the local quarries, mining marble that would eventually form City Hall in Albany, Grace Church in New York City, and Calvary Baptist Church in Ossining. Other convicts produced everything from boots to barrels.

- Partner Content -
A stereoscopic view of Sing Sing. Cross your eyes to view the prison in 3D. Robert N. Dennis / New York Public Library
A stereoscopic view of Sing Sing. Cross your eyes to view the prison in 3D. Robert N. Dennis / New York Public Library

By the 20th century, the tide of temperance began to turn. Merchants no longer wanted goods made from contract labor. New York Governor Daniel B. Hill legalized the electric chair to humanize execution. In total, 614 men and women were executed by the electric chair, called “Old Sparky,” until the abolition of the death penalty in 1972. The shackles of lockstep were unhinged, and inmates began exercising in the Sing Sing yard. Warden Thomas McCormack oversaw the first baseball game in 1914.

Still, Sing Sing was a grueling master. The facility saw 10 different wardens from 1900 to 1919. Rebellious inmates and crumbling infrastructure weighed heavily. The number of prisoners on record rarely matched the number in custody. Administrators abused prison funds and prisoners alike. To critics, the quickest way out of Sing Sing was as a warden.

But, it was Warden Lewis Lawes, appointed by Governor Alfred E. Smith in 1920, who ultimately transformed the aging Sing Sing back into a modern reformatory. Lawes used sports to teach discipline and embraced the outside world through famous performers. New York Mayor Jimmy Walker, Spencer Tracy, James Cagney, and Babe Ruth all stopped through.

Inmates landscaped the facility on their own and held a show each year for the Ossining community. By 1930, a new chapel, mess hall, laundry, bathhouse, and barbershop had been built. Bank robber Willie Sutton and Soviet spies Julius and Ethel Rosenberg spent time within the refurbished marble walls.

Today, Sing Sing holds about 1,700 inmates, has about 900 employees, and is considered a model correctional facility due to its innovative rehabilitation programs for inmates.

- Advertisement -

Movies including The Big House (1930), Angels with Dirty Faces (1938), and Analyze That (2002) were all set at Sing Sing. And Captain Lynds’ model still stands stone upon stone.

If you want to dive even deeper into the history of Sing Sing, check out these books:

Newjack: Journalist Ted Conover landed a job at Sing Sing Prison after his request to shadow a recruit was denied. He worked as a prison guard for a year, during which time he gathered notes of his experiences on his prison-issued notepad. The result is the in-depth work of eyewitness journalism, showcasing the brutal prison system and Conover’s struggles.

Sing Sing Prison: This book takes you back to the construction of Sing Sing and details the history of its inmates and visitors. You will learn about the first people found guilty of espionage and put to death at the prison in 1953. The book also includes rare photos from the prison’s archives, the Ossining Historical Society, and a private collection.

Sing Sing 614: In this book you’ll learn about the 614 inmates who were executed at Sing Sing. The man on the cover being tied to the electric chair, Joe Wood, was the first black man to be executed at the prison. And Gordon Hamby, who was known as the handsomest man on death row, had 800 women writing in to not to execute him.

Sing Sing: The Inside Story of a Notorious Prison: If you’re looking for a well-rounded book about the history of Sing Sing with original sources, this one is for you. Learn all about each period of the prison’s history and its notorious prisoners. There’s so much history behind the walls, from brutal punishments to famous visitors like Johnny Cash and Mother Teresa.

Related: A Look at Westchester County’s Prison System and the People Inside It

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

Our Best of Westchester Elimination Ballot is open through March 6!

Holiday flash sale ... subscribe and save 50%

Limited time offer. New subscribers only.