Two British loyalists, Captain Ebenezer Hathaway and Thomas Smith, were captured from the privateer boat Adventure while it was anchored off Long Island in Huntington Bay on April 7, 1781. The men were brought ashore in Stamford, transferred to Hartford and sentenced to New-Gate.
Less than two months later, the Connecticut Courant reported a prison breakout that remains the largest in the state's history. A crowd of prisoners, including the Tories Hathaway and Smith, rushed the New-Gate guards on the night of May 18, killing one and wounding others, and took off with the guards' weapons and ammunition. Twenty prisoners escaped.
On May 29, 1781, The Courant reported that "Sixteen of the prisoners who made their escape from New-Gate last week are since taken and returned to their former lodgings."
Hathaway and Smith were among the four who were still on the loose. They reached British-held New York and published their escape story in the New York Royal Gazette.
When Old New-Gate closed in 1827, 81 prisoners were transferred to a new penitentiary in Wethersfield. The Connecticut State Prison was a maximum-security facility, but the escapes continued.