Prisoner weapons on display.
Visitors admire the cutting-edge craftsmanship of Sing Sing.

Sing Sing Prison Museum

Field review by the editors.

Ossining, New York

Ossining tries very hard to be a gentrified village of quaint shops, poorly timed traffic signals, and moss-stained marble buildings. But it can't escape its dark secret. The marble was quarried by convicts. Down by the river, screened from public view, is one of America's most infamous prisons. And Ossining calls itself that to avoid any association with the waterfront calaboose that bears the town's original name: Sing Sing.

Replica Electric Chair.
The exhibit includes a replica electric chair made by convicts.

The prison is still there, providing long-term housing for 2,200 tenants who don't look kindly on tourists. But continuing interest by visitors about the prison "up the river" from New York prompted the village to create a museum in the Caputo Community Center, just down the street from the high school. It's the best prison museum in a village community center anywhere in the U.S.

The Sing Sing Museum presents a blend of understated historical correctness and gruesome thrills. You see pictures of prisoners being flogged bloody, but they're tastefully mounted and the practice is sternly chastised. There's an electric chair on display, but it's a replica, hand-crafted by Sing Sing's own Building Maintenance Vocational Class in 1991 (A real electric chair, supposedly one of several that fried 614 men and women at Sing Sing, is at the Klairmont Kollections Museum in Chicago).

Sing Sing alumni occasionally visit the museum with their families to reminisce about life in the Big House. According to our guide that day, the place is also popular with tourists from Canada.

"Some people blow through in two minutes," he said with a disdainful arch of his eyebrow. "Others, an hour-and-a-half and they're still back there."

Classic postcard.
A classic postcard of the famous chair.

Two Sing Sing cells are on display, in all their gray-and-insane-asylum-green glory. Floor-to-ceiling mirrors on the walls turn this modest effort into an endless cellblock. One cell has an open door so that visitors can sit inside for novelty photos. There's no tin cup to rattle against the bars but, given the number of kids wandering through, we understand not wanting to make this too real.

Confiscated prison weapons adorn a wall plaque, some still in their evidence bags, offering proof that Sing Sing's current population is as handy and resourceful as their marble-quarrying predecessors. "Inmates are convicted criminals," reads the accompanying sign, "and some of them continue their criminal ways when in prison."

One "shank" is made from two plastic forks bonded together with their middle tines removed. "Eye gouger," our guide explained, jabbing his index and middle fingers toward his face.

The guide, like all good prison museum employees, is an open cellblock door of lurid facts. "A lot of cons who got only 7-10 years left on their sentences don't ever leave their cells," he reveals. "They don't want to get killed!"

To make his point, he calls our attention to a particularly nasty-looking shank fashioned from a razor-sharp piece of twisted steel. "Somebody walks past you in the exercise yard, then wooosh!" He makes a sweeping arc with his arm. "Rips your neck wide open."

Local officials have for years sought state funding to remodel part of the prison into a museum and tourist attraction, hoping for success on par with San Francisco's Alcatraz. The project would cost $5 million to convert Sing Sing's old power house into the museum, with a link via a tunnel to a retired cell block. That may happen, some day, but until then we challenge Ossining to confront its past. Get those calendar-watching 7-to-10 inmates out of the jail and into the current museum! They can serve out their sentences as tour guides and living photo props in Olde-Timey striped suits and leg irons.

Replica cells.
Replica cells.

Sing Sing Prison Museum

Caputo Community Center

Address:
95 Broadway, Ossining, NY
Directions:
From NYC, Sprain Brook Parkway north to Taconic Parkway, exit at Route 133, go west all the way to US 9, then straight across to the Caputo Community Center. Or follow NYC's Broadway north into Westchester County, where it takes on a variety of names but is always US 9. You'll go through Sleepy Hollow country and eventually into Ossining. Go past its Main Street on the left, then take the next left to the Caputo Community Center and its parking lot.
Phone:
914-941-3189
RA Rates:
Worth a Detour
Save to My Sights

Nearby Offbeat Places

Eye of SauronEye of Sauron, Ossining, NY - < 1 mi.
Headless Horseman SculptureHeadless Horseman Sculpture, Sleepy Hollow, NY - 5 mi.
Headless Horseman BridgeHeadless Horseman Bridge, Sleepy Hollow, NY - 5 mi.
In the region:
Friends Apartment Building, New York, NY - 31 mi.

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