The second jail in the Colony was erected in Ipswich in 1656. Sixteen British prisoners were kept hostage in the cold and cruel stone jail during the War of 1812. A large brick House of Corrections was constructed in 1828 at the site of the present Town Hall on Green Street.
As the people of the Hamlet were financially stable, the burden of taxation for the support of the poor in the old town of Ipswich was considered to be an unjust imposition. The leaders of the parish petitioned Ipswich to be allowed to incorporate as the new town of Hamilton. 25 years later, the men of Chebacco petitioned the Legislature for incorporation as a separate town, and to not be held for any part of the new establishment for the relief of the poor in Ipswich. The following year, Chebacco Parish became the Town of Essex
On the morning of the 30th of March, 1662, the Ipswich jailer found that a prisoner had escaped, the first offense of this nature committed in the country.
After Dorothy demanded that the State conduct an investigation, the “Report on Insanity and Idiocy in Massachusetts” found that 68 insane or demented persons were being housed in the Ipswich jail.