- Historic Sites
Stone Walls Do Not A Prison Make
The horrors of Connecticut's maximum-security dungeon at Simsbury were notorious even abroad. Yet time and again its inmates proved that, with a clever escape plan, stone walls do not a prison make.
February 1967 | Volume 18, Issue 2
Among the prisoners privileged to participate in the new order was a champion of King George named Simeon Baxter, a free-spoken clergyman incarcerated for high treason. Over the years the prison population had known some stout leaders, but never one who could equal the vituperative Mr. Baxter. In the depths of Talcott Mountain he set up his pulpit, and on weekdays as well as on the Sabbath preached his doctrine of retribution, scorn, and escape.
Baxter modestly labelled himself “Licentiate in Divinity and Voluntary Chaplain to those Prisoners in the Apartment called Orcus,” but his sermons were very much at odds with the messages delivered every Sunday in the prison-yard nail factory by pastors from the surrounding countryside. Attendance at those services was compulsory. Surrounded by fixed bayonets, tractable prisoners were marched to benches before an improvised altar in the shop; the less docile were herded out of the pit in shackles and were chained to blocks while the minister propounded an orthodox discourse according to the gospel of Congress and Jonathan Edwards, and a choir of public-spirited ladies from Simsbury or Hartford chanted inspirational psalms.
The congregation was torn between the two philosophies, but Baxter’s sermons obviously made the deeper impression. Whenever he discovered a lagging spirit content to put up with the miseries of Newgate, the Licentiate in Divinity quickly restored the man to a proper perspective. Henry Wooster, sentenced to four years for participating in a Tory raid on a private home in Bethany, was a man after Baxter’s heart. Upon arrival underground, Wooster made a meticulous survey of the prison and concluded that the only possible route of escape was down the drain that had so recently been blockaded and barred.
Egged on by Baxter, he first contrived to fashion a key with which he could lock and unlock his fetters at will. Then from the nail shop he stole fragments of nail rods, concealed them in his clothes, and carried them below. He started to work, picking at the mortar which held the bars. One by one they were removed, so cleverly that they could be fitted back in place to conceal the evidence of tampering. With longer pieces of pilfered nail rod he started chipping away at the drain, breaking the mortar, prying out pieces of stone and hiding them in distant passageways.
Working his way night after night down the 100-foot drain on his belly and everlastingly hacking away, Wooster, thanks to the encouragement of Baxter and the help of a dozen companions, came within a few yards of freedom. Then, with the smell of the open world literally before him, near-disaster struck. From the ceiling a loosened boulder almost as big around as the passageway thudded down behind him, blocking his retreat. For a long time he lay in the drain contemplating permanent entombment. There were still several nights of work ahead of him before he could reach the outside, and even if his whereabouts was not discovered, his strength would not hold out that long. He shouted for help, but no one heard. Then, in desperation, he braced himself against the sides of his tomb and began to push the stone with his feet, using all the strength he could summon. It budged a fraction of an inch. He tried again. Hour after hour he strained against the stone, now scarcely rocking it, again rolling it several inches. He knew that it was near dawn, and the guards would soon be summoning the men to work. With a final Herculean effort he gave the boulder another shove; miraculously it slipped into a depression in the floor.
Barely able to stand up, Wooster appeared for roll call a few minutes later; the following week he led down the drain to freedom all the prisoners whose fetters he had been able to unlock. The evacuation was discovered sooner than the evacuees had hoped, and many of them were recaptured—but not the tricky Wooster. Climbing a hemlock a few yards from the exit, he hid in the topmost branches and for twenty-four hours watched his pursuers milling around below. When they had given up, he eased himself down and sauntered away unmolested.
Those who failed to escape with Wooster had to wait for another chance until the following year, when headquarters were again set afire. A magnificent blaze that reddened the sky all the way to Hartford was kindled by privileged trusties housed in the Jug. A scared guard, Abel Davis, was responsible for releasing those in the pits. For his humanity he was rewarded with three months’ imprisonment. Davis balked at the treatment, going over the heads of his superiors and writing directly to the General Assembly for remission of his sentence:
Whare as I was confided of mis Deminer on the count of Newgate being burnt as I had command of said gard and was ordered to be confind three month for disabaing orders … but I did all in my power to distingus the flame, but being much frited … I thot it best to let out the prisoners that war in the botams as I had just time to get the gates lifted before the hous was in flames. …
But the long-suffering Assembly was much too mortified to grant favors.