The first Essex County gaol (jail) was erected in Ipswich across from the Meeting House in 1652. The Court paid the keeper 5 shillings per prisoner and ordered that each prisoner should additionally pay the keeper before they be released for “their food and attendance.” Those who were unable to pay for their food were allowed only bread and water.

The second Ipswich jail, the “Old Gaol” was built in 1771 at Meeting House Green, and was moved to its current location on High Street in 1808

First Jail Break in the Country

On the morning of the 30th of March 1662 the worthy constable and jailer and the community generally were astonished to find that a prisoner had escaped by jail-breaking, which according to Thomas Franklin Waters was the first offence of this nature committed in the country. Upon being recaptured he complained that he was cold and pulled up the flooring for his escape. As there is no mention of a chimney in the contract, confinement in cold weather must have been particularly cheerless.

Severe Punishments

Puritan punishments were severe. For breaking prison, Ipswich Henry Spenser was sentenced to be severely whipped and branded in the forehead with a letter B and pay a fine of 5 shillings. Samuel Shattuck, Nicolas Phelps and Joshua Buffum had been absent from public worship in Salem and were all sentenced to be fined. For persisting in their course & opinion as Quakers they were led across the Green to the prison, whipped, fed on bread and water and compelled to work on hemp and flax, and no one was allowed to speak to them. Murderers were imprisoned there until the day of their doom delivered them. Those under suspicion of witchcraft were guarded there, including Giles Corey who was pressed to death in Salem because he refused to plead to the charge of witchcraft.

The Olde Gaol

Old Gaol in York, Maine. The old jail building in Ipswich, built in 1771 also had a gambrel roof and probably looked very similar before it was moved to High Street and rebuilt as a residence.

The old jail continued to serve its purpose until 1750 when it was reputed to be in such a ruinous condition and utterly insufficient that the Court ordered it should be used no longer. The town of Ipswich, naturally, decided to extensively repair it. Nonetheless, after prolonged repairs the sheriff reported in 1769 that the building was still very defective, and plans for a new jail commenced. The old jail was taken down and the new jail was completed in 1771, a two-story gambrel roof building in which the lower floor served as the jail and the rooms under the roof were used for the “House of Correction,” apparently two separate functions.

The County found the small attic rooms insufficient, and in 1806 a new jail of stone was was completed near what is now the Ipswich Town Hall. In 1808 the site of the old Gaol was sold to Rev David Tenney Kimball, who built his parsonage there, across from the church. The Old Gaol was moved up High Street to its present location today. The gambrel roof was removed and a second floor was added with a gable roof.

The Old Stone jail

The Old Stone Jail in Hanover ,MA was built early in the 19th Century. The Ipswich stone jail built in 1808 was probably similar. This was the third Ipswich jail and was used until 1828. British prisoners were kept in such horrid conditions in the Ipswich stone jail that the Massachusetts legislature ordered them to be released.

The new stone jail on Green Street, built in 1806, 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.

The Green Street Jail

A new large jail/insane asylum was built on the Green Street location in 1828. It was torn down in 1933 to make room for the former high school, now serving as the Town Hall. The prison workhouse still stands and was remodeled into a modern senior residence center known as Whipple Riverview Place .

The Green Street Jail was the fourth and final Ipswich jail, and was used from 1828 – 1933.
The Ipswich jail, demolished in 1937 to build the high school building which is now the Ipswich Town Hall.
The Ipswich jail, demolished in 1933 to build the high school building which is now the Ipswich Town Hall. Photo courtesy Bill George
The Ipswich jail master lived in front of the jail, on Green St.
The Ipswich jail master lived in front of the jail, on Green St. Photo courtesy Bill George
Inside the Ipswich jail, demolished in 1933. Photo courtesy Bill George
Inside the Ipswich jail, demolished in 1933. Photo courtesy Bill George
View of the Ipswich jail on the left, from Great Cove

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