Nantucket built its first jail in 1696 on Vestal Street. In 1805 taxpayers decided to spend $2,090 (roughly the cost of building a whaleship at the time) to build a new, sturdier penal facility also on Vestal Street. Opened in 1805 and dubbed the “New Gaol,” the wooden structure represents colonial architecture with exceptional reinforcements.
The New Gaol was constructed using massive oak timbers with iron bolts running the length of the walls, iron rods across the windows and heavy wooden doors reinforced with iron.
The solidly-built jail forced prisoners to come up with creative escape plans. Archival material held at the NHA Research Library contain many accounts of successful and unsuccessful prison-breaks, including one of a 15-year-old boy who crawled out the chimney flue, and of a prisoner who had a key delivered to his second floor window by a woman using a block-and-tackle pulley system constructed for the purpose.
1933 saw the last prisoner housed in what is now known as the “Old Gaol.” The town closed the property and deeded it to the Nantucket Historical Association in 1946.