These historical images are from the personal collection of a
Sing Sing Prison Museum board member.
There are many stories to be told - hover or tap on the photograph to reveal them.
The 1,200 cells in the 1825 cellblock were a mere 3'x 3'7'. Each cell came with a cot, a bible and a bucket, as there was no plumbing. Electric lights were added in early 20th century. The old cellblock was taken out of service in 1943 and its iron doors used as scrap for the war effort.
Lewis Lawes served as warden from 1920 to 1941, the longest tenure in Sing Sing history. A former prison guard turned penologist, he was a celebrity in his own right, producing books, plays, radio shows and other media based on his experiences as warden.
In the 19th century, medieval-style punishments were applied frequently and without mercy. the "shower Bath" was akin to waterboarding, and made the prisoner feel as if he was drowning. sometimes he did. all such tortures were banned in the early 20th century.
in January 1983, when the prison was called Ossining correctional facility, a group of inmates took 16 guards hostage in cellblock A for three days. Worried friends and relatives waited for word on their fate.
Thomas Burke escaped in 1921. Like most of Sing Sing's inmates, he was from New York City.
Of the 614 people put to death in Sing Sing's electric chair, Julius and Ethel Rosenberg were the most controversial. Their Cold War executions brought international attention to Ossining in the early 1950s.
"20,000 Years in Sing Sing" was based on warden Lewis Lawes' 1931 memoir of the same name. Starring Spencer Tracy and Bette Davis and filmed in the prison, it was one of many movies set in Sing Sing in the 1930s.
People from all walks of life passed through Sing Sing's gates. Richard Whitney, the former president of the New York Stock Exchange, served three years and four months for embezzling from brokerage clients. Released in 1941, he went on to run a dairy farm upstate.
Frank (The Dasher) Abbandanno and Harry (Happy) Maione, convicted of murder, leave Grand Central Terminal for Sing Sing in 1940. They died in the electric chair on
Feb. 19, 1942.
Escapes were commonplace. The deadliest was on April 14, 1941, when three inmates shot a guard and escaped prison grounds. They engaged in a shootout near the train station, in which a convict and a village police officer died. The surviving two inmates forced a fisherman to row them across the Hudson River. They were captured in Rockland County.
The prison has employed many Ossining residents. Jesse Collyer, Jr., ran the vocational program for 27 years, along with serving as village mayor in the 1950s, followed by town supervisor. He was descended from a famous 19th century shipbuilding family.
Invented in the late 19th century, the electric chair made use of a new technology--electric current--as a form of capital punishment. Executions in "Old Sparky" were considered more modern and less public than hanging. The electric chair spread to prisons around the U.S. and is still in use today.
Inmates walk uphill to their cellblocks in 1940. The prison complex, once hunkered on the waterfront, was rebuilt on the west side of the train tracks in the 1920s and 1930s during the tenure of warden Lawes.
A young man studies within the walls of the prison in the late 1960s. Pell grants were once available for inmate education; today, private nonprofits like Hudson Link for Higher Education run college degree programs in prisons throughout New York state.
The 19th century prison on the waterfront did not have a wall around it until 1877, 50 years after it opened. Today, an imposing and inpenetrable wall rings the entire prison. the Guard towers date to the 1930s.
Thomas Mott Osborne was Warden for only a short time, from 1914-1916, but his influence was immense. He created the mutual welfare league, which encouraged education and reformation, and posed the question: "shall our prisons be scrap heaps or human repair shops?"
The death house at Sing Sing housed men and women sentenced to death. The walk from the cells to the electric chair was dubbed "the last mile." the last execution was in 1963. This building still sits on the waterfront but is used as classrooms and a gym.
This illustrated view of the prison from the Hudson River in the 1860s shows the long cellblock, the workshops and the (disproportionately large) greek- revival "Female prison" on the hill. the only structure left standing today is the ruin of the old cellblock.