The Old Gaol, 83 High Street was built in 1771 at the location of the David Kimball house on Meetinghouse Green but was moved here in 1808. The new stone jail on Green Street was a notoriously cruel and controversial place. Sixteen British prisoners were kept hostage there during the War of 1812 and treated so cruelly that they were removed by the District marshal.
In 1814 the Federalist-controlled state legislature ordered that all British prisoners of war be released in direct opposition to the mandate by President Madison that they be so imprisoned. A new large jail / insane asylum was built on the Green Street location in 1828 and was torn down in 1933.