• Nyack Boat Charter

Sing Sing Prison: Up the River

Updated: Mar 9

Barely a charter goes by where we don't discuss Sing Sing, located on the shore in Ossining, and its imposing set of structures are visible, 5 miles up the river, even as we start out in Nyack. It would be easy to take up an entire two hour charter talking about the maximum security prison.


Sing Sing from the Hudson River

An exciting addition this year is that a new museum is in the works to open, which will include a structure outside the walls, and one inside in the powerhouse built in 1936. Eventually they will connect the powerhouse with the original 1925 cellblock.


The name Sing Sing comes from the Sinstink native American tribe, and the words "sinck sinck," meaning Stone on Stone. The village of Ossining was actually called Sing Sing, but in 1901 residents changed the name to Ossining, to disassociate the village from the notorious prison.


In fact, the residents of Ossining felt the need to change the name from Sing Sing due to a boycott on prison-made goods, and it hurt local businesses in the confusion.


Prison Yard circa 1855

The prison is old, the fifth in New York State. Construction started almost 200 years ago, in 1824. The first few cell blocks were made by the inmates themselves using marble excavated from a nearby quarry. The prison was considered a model because it turned a profit, using the labor of the inmates to continue quarrying the marble, that was used for many other projects, including the notable Lyndhurst (just down the river in Tarrytown) and Grace Church in Manhattan.


View from Westerly Restaurant 200 yards north of Sing Sing (Al Vento anchored)

The contract labor model was controversial on many levels, including from businesses and labor unions that felt the prison had an unfair advantage of free labor to compete with them. Sing Sing then diversified their production from just quarried stone to shoes, saddles, locks, hats, and other items.


This profit venture was supposed to tie in with the philosophy behind the "Auburn System", which worked the inmates under harsh conditions which was supposed to embrace the idea of moral reformation. But the profit motive eclipsed the purpose of labor as part of reforming the inmates. Sing Sing's history shows that in clash between ideals and profit, money was the clear winner, as is often does.


There are three well known sayings coined at Sing sing: "Up the River"; "The Big House","The Last Mile". The term "up the river" started in the 1890s when serious offenders would be taken from the downtown "tombs" in lower Manhattan 30 miles north, up the Hudson River, to Sing Sing, in Ossining. The term originally referred to Sing Sing specifically, but then became a general term about going to prison.


Sing Sing became notorious for its "death house", where 614 people were executed by electric chair ("Old Sparky") between 1891 and 1963. The most famous execution was probably Julius and Ethel Rosenberg, who were executed for espionage for the Soviet Union. "The Last Mile" was a saying started from the walk inmates had to make to their execution.


Inmates played both football and baseball in the big leagues. In 1929, the Yankees came to Sing Sing to play an exhibition game. The Yankees beat the Ossining Orioles 17-3, and Babe Ruth hit 3 home runs, one that is said to be his longest hit ever, at 620 feet, arguably the longest home run ever hit.


Birdseye View

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