Tory prisoners called this Connecticut cave the “Catacomb of Loyalism” during the Revolutionary War

Old Newgate’s Underground Hell and Great Tory Escape

Old Newgate Prison in Connecticut became America’s most notorious political prison when Patriots locked up dozens of Loyalists in underground copper mines during the Revolution.

Connecticut passed harsh treason laws in 1781 that sent King George supporters to these dark caverns with no hope of exchange or parole.

Up to forty Tories at a time suffered in the depths, facing life sentences just for their beliefs. Then came May 18, 1781, when a prisoner’s wife helped stage the largest prison break in American history.

Twenty-one men killed a guard and escaped into the night.

The dramatic breakout from this underground hell reveals just how brutal the fight for American independence really became.

Copper Miners Accidentally Created America’s First Prison

In 1705, sixty-four Simsbury folks started America’s first copper mining company. They used the money to pay town bills and hire a teacher for local kids.

By 1773, copper became scarce and profits dropped. That May, three local men checked out the mines and saw an opportunity.

They created a 15 by 12 foot room near the first shaft to make a prison.

The colony bought the remaining mining lease and added an iron gate at the top of the 25-foot shaft. John Hinson, doing 10 years for burglary, became the first prisoner in December 1773.

He escaped just 18 days later using a rope down the larger shaft.

Patriot Anger Turned Old Mines Into Political Dungeons

As tensions grew in the colonies, Patriots began targeting Loyalists. People loyal to the King faced beatings, tar and feathering, and worse.

Anyone caught joining British forces or robbing wasn’t treated as a war prisoner but tried in court. This meant loyalists couldn’t be pardoned, exchanged, or freed like normal war prisoners.

About 60 loyalists, called Tories, ended up in Newgate during the Revolution.

Patriots nicknamed it the “catacomb of loyalism” – a dark, wet hole 40 yards underground where political enemies went.

Connecticut Made Supporting Britain A Death Penalty Crime

In February 1781, Connecticut passed a law against high treason. The law said any American who showed loyalty to King George committed treason.

The punishment? Death or prison at New-gate.

People who joined enemy forces, robbed, or looted faced death, whipping, or the mines instead of war prisoner status. Public opinion turned harsh against Tories.

Some colonies even let citizens shoot Tories found beyond their property lines. This system kept loyalists from being exchanged and released.

Two Defiant Loyalists Refused To Recognize American Courts

Rebels caught Ebenezer Hathaway and Thomas Smith off Long Island in April 1781. They sailed their “Privateer Boat Adventure” when whaleboats nabbed them at night.

Hathaway served as Captain with Smith as crew. During their trial, judges pushed them to plead guilty.

Both men refused to enter any plea. They claimed they were British subjects and didn’t accept the American courts as real.

Their punishment? Prison without bail at New-gate until they accepted the court’s power.

Their official sentence read “sentenced until pleads indictment” – locked up forever unless they gave in.

Life Underground Turned Men Into Desperate Escape Plotters

Prisoners called New-gate a “dark dismal cavern” where “armies of fleas, lice, and bedbugs covered every inch of the floor. ” The ground sat under five inches of “slippery, stinking filth.”

Murderers and outspoken loyalists lived together in awful conditions. At first, only five or six loyalists went to the prison.

Soon that changed, with thirty to forty loyalists locked up just for their Crown support. Most Tories landed there for small offenses like “having a small quantity of tea and other British imports.”

Despite more guards, New-gate’s security stayed poor, shown by many escape attempts.

Guards Got Sloppy With Prison Security Rules

After earlier prison breaks where inmates burned the blockhouse, officials rebuilt it stronger with double hatches at the main entrance. They added twenty-four guards under officers.

But over time, guards grew careless. They began treating prisoners nicely, even allowing visitors.

On May 12, 1781, one woman got permission to visit her husband in the mine shaft. Six days later, Abigail Young showed up asking to spend an hour with her jailed husband Jonathan.

Guards searched her carefully, then took her to the hatch at the top of the shaft, not knowing what would happen next.

A Wife’s Visit Hid A Violent Escape Plan

Abigail’s visit wasn’t just to see her husband but part of a planned prison break. While two officers lifted the shaft’s gate, prisoners violently pushed it upward from below.

Men armed with rocks and metal bits climbed up the ladder into the blockhouse. They opened the door, letting about twenty inmates rush toward freedom.

The shocked guards got overpowered and lost their weapons in the chaos.

Ebenezer Hathaway and Thomas Smith, the British loyalists who rejected American courts, led the group of prisoners after weeks of planning underground.

Prisoners Turned The Tables On Their Guards

The escapees caught both the night guards and those sleeping in quarters. Fighting their way out, they killed six guards.

All guards, hurt or not, got dragged down into the prison caves.

The escaping prisoners left wounded guardsmen and loyal Tories “laid upon the floor, weltering in their blood. ” This happened even though the prison had 27 soldiers with muskets and swords.

Twenty-one prisoners broke free in the bloody revolt, making their underground hell into their jailers’ prison.

Tories Pulled Off America’s Biggest Colonial Prison Break

The May 18 escape stands as the largest in New-gate’s history.

Most escapees were locked up for “illicit trade,” “being a Tory,” “joining the enemy,” or “trying to join the enemy” – all crimes listed in the February 1781 Act.

Their teamwork showed how political prisoners from different backgrounds united against their captors. Records suggest about half of all inmates held at Newgate during the war managed to escape somehow.

For Hathaway and Smith, breaking out meant fighting what they saw as unfair political imprisonment by a government they didn’t accept.

Most Escapees Tasted Freedom Only Briefly

Sixteen of the twenty-one escapees got caught and sent back to the underground cells. A few lucky ones reached British lines and safety.

The escape showed how Loyalists kept fighting what they saw as an illegal government.

Patriots used fear of Newgate to scare Loyalists into behaving, with many signing loyalty oaths when threatened with the mines.

Some historians think the poor treatment of Tories at New-gate gave the British reason to mistreat American prisoners on their prison ships, creating a cycle of cruelty.

The Dark Legacy Of America’s First Political Prison

On November 6, 1782, fire destroyed the wooden prison buildings, allowing another inmate escape. The facility later became America’s first state prison in 1790 but closed in 1827 after being deemed inadequate.

One unnamed prisoner wrote: “I have here unjustly suffered so much, and seen, and heard so much, that I am not as I was; my nature has become changed and hardened.”

The Newgate breakout showed how political repression during wartime united desperate men against their captors.

Old New-Gate Prison represents one of the most shocking chapters in American penal history and the first systematic use of underground imprisonment for political enemies.

Visiting Old Newgate Prison, Connecticut

Old Newgate Prison at 115 Newgate Road in East Granby shows where Connecticut locked up Tory prisoners during the Revolution in terrible underground conditions.

Admission costs $10 for adults, $8 for seniors, and $5 for kids 6-17. The prison runs May through October, Thursday through Monday from 10am to 4:30pm.

You can take 30-minute mine tours at 52 degrees or explore the prison yard ruins and guardhouse exhibits yourself.

This article was created with AI assistance and human editing.

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