5. Blackwell Island Prison

Photo from New York Public Library

The prison on Blackwell Island (now Roosevelt Island) continued the trend of putting undesirable populations away from civilization, but with the added advantage of being on an island, away from the onward march of development on Manhattan. Unlike earlier prisons in New York City, the prison on Blackwell Island was a truly fortified structure. The cornerstone was laid in 1828 and the main building completed in 1832. It was 600 feet long and 4 stories high. The inmates worked in the Blackwell Island quarries and performed construction work on Hart Island, Randall’s Island and Ward’s Island.

6. Ludlow Street Prison

The jail at Ludlow Street Prison, opened in 1862, was a New York Federal Prison located at Ludlow Street and Broome Street. It has had several notable detainees, including Boss Tweed (who died there) and Victoria Woodhull, the first female candidate for the United States Presidency. It was known as a prison for civil crimes rather than criminal ones, and the incarcerated could pay more for better accommodations. According to Ephemeral NY, the prison included “a reading room, grocery store, and cells with comfy beds and curtains. It looks more like a posh university club.” Today, the prison site is home to the Seward Park High School.