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, horrible 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 still bears the town's original name: Sing Sing.

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

The prison's 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 surely the best prison museum in a village community center anywhere in the US.

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 in flawless detail by Sing Sing's own Building Maintenance Vocational Class in 1991. The real chair, which fried 614 men and women over its long career, was on loan for awhile to the Newseum, Arlington, VA.

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 says 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 army barracks 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," the curator explains, 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!"

Aqueduct display.
Bonus: first aqueduct into New York City, one of the 19th century's greatest engineering feats.

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."

We feel bad for the prisoners of Sing Sing. Out of a sense of compassion and good clean fun, we challenge Ossining to confront its past. Get those clock-watching 7-to-10 inmates out of the jail and into the museum, where they belong, to serve out their sentences as tour guides and living photo props in Olde-Timey striped suits and leg irons.

Update - January 2005: Local officials are seeking state funding to convert part of the Sing Sing Correctional Facility 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, and link via tunnel to a retired cell block. Thousands of serious convicts continue to be incarcerated in other parts of the Sing Sing prison.

Sing Sing Prison Museum

Caputo Community Center

95 Broadway, Ossining, NY
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.
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:
Mosaic House of Boerum Hill, Brooklyn, NY - 34 mi.

More Quirky Attractions in New York

Stories, reports and tips on tourist attractions and odd sights in New York.

Explore Thousands of Unique Roadside Landmarks!

Strange and amusing destinations in the US and Canada are our specialty. Start here.
Use's Attraction Maps to plan your next road trip.

My Sights

My Sights on Roadside America

Map and Plan Your Own Roadside Adventure ...Try My Sights

Mobile Apps

Roadside America app: iPhone, iPad Roadside America app for iPhone, iPad. On-route maps, 1,000s of photos, special research targets! ...More

Roadside Presidents app: iPhone, iPad Roadside Presidents app for iPhone, iPad. POTUS landmarks, oddities. ...More

New York Latest Tips and Stories

Latest Visitor Tips

Sight of the Week

Sight of the Week

Nessie: the Yaquina Bay Monster, Newport, Oregon (Jan 17-23, 2022)

SotW Archive

USA and Canada Tips and Stories

More Sightings

Favorite Quirky City Sights