A museum whose mission extends beyond the history of the Sing Sing Correctional Facility to exploring incarceration in America today is expected to open this October in the village where the prison was founded 200 years ago.
A ceremony in what will be the first-floor exhibition gallery of the Sing Sing Prison Museum took place in the Olive Opera House building in the Village of Ossining on Feb, 10.
The timing coincides with the bicentennial of the prison’s founding, when men from Auburn state prison came by barge down the Erie Canal and then down the Hudson River to begin building a prison that would incarcerate them.
“Almost every chapter in America’s criminal justice system has a few pages written at Sing Sing,” the museum’s executive director, Brent Glass, told several dozen guests during the ceremony.
The museum, Glass said, would not only display objects from its collection, but would spark deeper conversations about criminal justice.
“We are sharing stories of incarceration and reform, past and present, and bringing people together to imagine and create a more just society,” he said. “We’re using this amazing, extraordinary history of Sing Sing as a resource to help us understand not only the history of this place but also to shed light on contemporary issues concerning criminal justice.”

The museum’s 1,000-square-foot first-floor gallery will host the first exhibit on Sing Sing history and will include participation by local organizations involved in prison reform today including Hudson Link For Higher Education in Prison and Rehabilitation Through The Arts.
The museum will eventually occupy storage and gallery space upstairs in the 13,000-square-foot building, which is currently the home of Hudson Valley Books for Humanity.
The museum’s investment in the Opera House is $1.5 million and may increase in the future, Glass said, with funding coming from the National Endowment for the Humanities, New York State Environmental Protection Fund, Tow Foundation and private contributions.
Walking tours around the outside perimeter of the prison are scheduled to resume weekends starting in April, said Amy Hufnagel, the museum’s assistant director.
Tours of the ruins of Sing Sing’s original 1825 cellblock, built to hold 800 cells and nicknamed “The Big House,” are in the planning stages.
An exhibition on religion, reform and rehabilitation for which the museum received a $2.5 million grant is still in the planning stages, Glass said, with a projected open in either 2027 or 2028.
The idea for creating a museum dedicated to one of America’s most infamous prisons dates back to the late 1980s, with a series of stops along the way before landing in the former opera house on Central Avenue.
The facility was originally to be housed in a building outside the prison property known as the “powerhouse,” which was once home to the turbines which powered the prison, as well as including the original cellblock.
The Olive Opera House, which dates from 1865, is owned by the Fan family, who received a $1.5 million state Downtown Revitalization Initiative grant to redevelop the property for mixed uses.
Twisne and Madeline Fan, whose father George Fan bought the building 45 years ago, were at the Feb. 10 “wall-breaking” ceremony. The Fans, who grew up in Ossining, said their mother used the space for painting and a Feldenkrais studio.
Besides the bookstore and museum, the building’s top floor can be rented out to host performances and arts programming.
“We’re so interested in keeping community access to it, ” Twisne Fan said of the former theater. “We feel like there’s a really nice mesh of ideas and goals, so we’re ready to start.”