How a simple family visit became Connecticut’s bloodiest prison break of the Revolutionary War

Loyalist Prison Break at Newgate Prison in 1781

Deep beneath the ground in East Granby, Connecticut, sits Old Newgate Prison, America’s first state prison and the site of one of the most daring prison breaks in Revolutionary War history.

Visitors today can explore the underground copper mine shafts where prisoners were held in horrific conditions during the 1700s.

But few know about the violent escape that happened here on May 18, 1781, when twenty prisoners stormed out of their underground hell, killed a guard, and made a desperate run for freedom.

Most were British Loyalists who refused to accept American authority, and their breakout became the largest mass escape in Newgate’s history.

Here’s how a simple family visit turned into a bloody fight that shook Connecticut’s Patriot government.

Connecticut Went After Loyalists With Death Threats

Connecticut passed a law against treason in February 1781, targeting anyone loyal to the British. The law hit British supporters hard, with death sentences or lockup in Newgate Prison.

Patriots didn’t treat these Loyalists as war prisoners, which kept them from being swapped back to British lines.

As the Revolutionary War heated up, American officials cracked down on anyone they thought might help the enemy.

Raiders Caught During Night Attack

Ebenezer Hathaway and Thomas Smith sailed their boat “Adventure” attacking American ships until April 7, 1781. Rebels in whaleboats surprised them during a night raid near Long Island.

Americans quickly took their captives to Connecticut and charged them with “joining the enemy” under the new treason law.

The men spent weeks in Hartford jail before moving to Newgate Prison, known for its tough conditions.

Loyal Brits Wouldn’t Accept American Courts

In court, Hathaway and Smith stood firm. When the judge asked for their plea, both men refused.

They said they were British subjects and wouldn’t accept the court’s right to try them. Their stance rejected the entire American legal system.

The court sent both men to Newgate “until pleads indictment” with no chance of bail.

Old Mine Prison Made Life Miserable

Guards lowered Hathaway 67 feet underground into a former copper mine. The prison had just one air shaft, and workers burned charcoal to cover up the smell.

Up to a hundred men shared the tight space without sunlight and only basic toilets. Prisoners called Newgate “Hell” for good reason.

The wet, dark conditions spread sickness quickly. Guards rarely came down, watching from above instead.

Twenty Prisoners Planned Their Getaway

Three weeks after arriving, Hathaway and Smith joined other prisoners planning to break free. They told fellow inmates they would take the first chance to escape, even if they might die trying.

Prisoners working in the kitchen found a way to break the lock on the door to the exit ladder. The men watched when guards opened the shaft door and gathered weapons from rocks and metal scraps.

Open Gate Gave Prisoners Their Chance

On May 18, 1781, prisoner Young’s wife came to visit him underground. Guards searched her before two officers started lifting the heavy gate to let her down.

Twenty prisoners, mostly fellow Loyalists, gathered at the bottom of the shaft.

The prison had 27 soldiers with guns and swords that day, though many were off-duty or sleeping when the wife arrived.

Prisoners Attacked With Surprising Force

As officers lifted the gate, prisoners pushed it upward with great strength. Hathaway led the charge, climbing up the ladder with rocks and metal as weapons.

The men knocked down the two officers working the gate. The sudden attack caught most guards by surprise.

Prisoners rushed through the opening, overwhelming the unprepared guards who had no time to grab their weapons.

Guard Died Fighting Back

Guard Gad Sheldon fought to stop the escaping prisoners and lost his life. Six more guards got badly hurt in the fight.

The prisoners quickly grabbed muskets from sleeping guards and used them against the remaining security.

The fight turned the prison yard into a battlefield, with the outnumbered guards falling to the determined escapees.

Former Prisoners Locked Up Their Guards

After beating all the guards, the prisoners dragged them down into the dungeon they had just escaped. The men locked their former captors in the dark prison cells.

The twenty escapees gathered all weapons and bullets from the guardhouse. Armed with stolen guns, the former prisoners walked away from Newgate as free men.

Big Escape Shocked Officials

The twenty escaped prisoners slipped into the Connecticut countryside at night. This became the biggest breakout in Newgate’s history.

The men split into smaller groups to avoid getting caught, using their knowledge of the area to dodge search parties. News of the escape spread fast, shocking American officials who thought Newgate was secure.

Freedom Reached New York for Lucky Few

Within a week, search parties recaptured sixteen of the twenty escapees and returned them to Newgate’s underground cells. Hathaway and Smith proved more fortunate, successfully reaching British-held New York City.

Their journey took them through hostile territory where they risked execution if caught.

The two Loyalists made it to safety behind British lines, their successful escape becoming a powerful symbol of defiance against Patriot authority.

Their story spread through Loyalist communities, inspiring others who remained loyal to the Crown during the final years of the Revolutionary War.

Visiting Old Newgate Prison, Connecticut

Old Newgate Prison in East Granby lets you explore America’s first copper mine turned Revolutionary War prison.

You can walk through the dark underground tunnels where loyalists were held before their famous 1781 breakout. Check out the guard post where a jailer was killed during the escape.

The museum has artifacts from the prison days, including leg irons and original cell doors. The site is open May through October, with special events about the loyalist escape during summer months.

This article was created with AI assistance and human editing.

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