Chauncey Judd

Prison Life

Let us draw a picture of daily prison life in the Newgate of Connecticut One hundred years ago. At daybreak, summer and winter, the heavy iron trap-door covering the shaft is unbarred, and by the united strength of two men thrown open. A guard of soldiers with loaded muskets are drawn up in line before it. A bell is rung, summoning the convicts from the depths below to their daily toil. Slowly and painfully they ascend the perpendicular iron ladder, forty feet in length, their limbs heavily loaded with both handcuffs and fetters. They come forth in squads of three each, followed by a guard. Unable to walk, they hobble along the way to the work-shop, where they are placed at their work. Then another squad follows in like manner, till all are thus disposed of. Some are chained by the leg to their forges, others to wheelbarrows, and such as are vicious and refractory have iron collars suspended from the roof locked about their necks. The guards take their stations in the shops, the handcuffs are removed to allow the use of their hands, and the labors of the day begin.

Twice during the day work is suspended, and an hour is assigned for meals. Pieces of pickled pork or beef are brought in and distributed, one to each man. These are washed and boiled by each at his forge, in the water provided for cooling the iron. One pound of bread, a few potatoes, and a pint of cider make up the rest of the daily ration, varied sometimes by peas or other vegetables. Each one divides his rations for the day to suit himself, and they are allowed to exchange with each other, to barter, buy and sell, at their pleasure.

Regular tasks of labor were assigned the prisoners, and when these were finished they might work for themselves or for others. In this way some of them acquired considerable sums of money. The ingenious made trinkets, which were readily sold to visitors. It sounds strangely enough in this day to state that the warden of the prison kept a tavern near by, where not only visitors, but the convicts themselves, might procure liquors, cider, tobacco, or whatever other luxuries they desired. He who could muster enough money would prevail on some one of the guard to escort him over the way to the inn, there the good-natured Captain Viets would deal out the coveted refreshment to them both.

For neglect of duty and other offenses the men were punished by flogging, confinement in the stocks, double or triple sets of irons, hanging up by the heels, etc. Everything of this sort tended to inflame their anger and revenge, and seldom was any appeal made to their reason or better feelings. The men were allowed at all times to converse with their keepers and with each other.

At four o'clock in the afternoon the tasks of the day were finished. The handcuffs were replaced, the collars and fetters unlocked, and with the same leaping and hobbling, the men, unless granted the indulgence of remaining for overwork, as already stated, made their way back to the pit. As they passed the trap, a bit of candle, one inch long, was given to each; then, holding up his shackles as best he could, he crept backward down the ladder to the regions below. If he had saved anything from his breakfast or dinner he was permitted to carry it with him for supper; if not, he must go without till morning unless he could buy or beg from others.

Arriving below, be might retire at once to his heap of straw, or join his fellow-convicts in whatever recreation or work of mischief their inclination might prompt. There was no restriction of any kind upon, them, except that of confinement. Conversation, gambling, practical jokes on each other, plans for escaping, and schemes of crime and adventure to be executed after their departure, filled up the dismal hours till weakness compelled them to sleep, to be aroused again at the inexorable call of the bell at daybreak the next morning.

It must be left to the imagination to depict the scenes which the walls of those deep caverns witnessed during those hours of license. By carefully husbanding their candle-ends they could manage to have light most of the time. Not infrequently did they contrive to free themselves from their handcuffs by picking their locks, or by using keys of their own manufacture. Their friends were allowed to visit them freely, and besides supplying them with money, often smuggled among them implements to aid them in effecting their escape.

Henry Wooster was one of those who had succeeded in releasing his hands from their fetters at night, being careful, of course, to replace them before going up to his work in the morning. One of the first things he attempted was to make a thorough exploration of the caverns, to see if there was any possible way of egress. For this purpose be forced himself into one of the drains which discharged the waters of the mine. This, after the occupancy of the mines as a prison, had been carefully built up with stone and mortar, leaving only a narrow channel, which was supposed to be thoroughly secured by iron bars. But patient labor laughs at obstacles. Watching his opportunities, Henry contrived to conceal in his clothes fragments of the rods of which nails were made, and carry them below. With these he picked out, little by little, bits of the mortar until the bars were loosened so as to permit their removal. In the same way he enlarged the drain in some of its narrowest places, and after many weeks of assiduous toil found himself near the outer orifice.

Redoubled exertions followed, in which he was aided, as far as possible, by others who had the use of their hands. It was a fatiguing and most dangerous task. The straitness of the passage barely permitted him to drag himself along it without the power of turning, and to get back was still more difficult. Once, indeed. while far within, he gave himself up for lost. A stone overhead, which he had loosened partially, fell into the drain after he had passed, effectually closing it like a portcullis, and debarring his return. Unable to reverse his position, or reach it with his hands, he concluded, for a time, that his last hour had come, and that he must perish in his terrible prison. His cries for help could scarcely be heard by the other convicts, and if heard, it was doubtful whether they could retrieve him. It was an awful moment for the wretched criminal, extorting even from his hardened heart an agonizing supplication for mercy from Him to whom be had never prayed before.

At length, on pressing the stone with his foot, Henry perceived that it was loose, and continuing to work it as far as he was able, it finally fell completely through from the place where it hung suspended into the drain. Further effort showed that he could push it a little along the passage behind him. But would it pass the whole distance? – for if there was a single place too small for its dimensions, he would be as inextricably shut in as if the drain had been hermetically sealed.

Bracing himself against the sides of the Channel, and pressing the obstacle with all his strength, he succeeded at length in getting it to a little depression or hollow on the bottom, which would permit of his passing over it. With desperate energy he crowded himself by, and at last emerged into the prison a little before the daybreak bell sounded to call the men to their labor. He had been in the drain all night, and came forth bruised, bleeding, and utterly exhausted. It would not do, however, to let his suffering condition be known, for this would inevitably lead to a search and exposure; so donning, with the help of his comrades, his garments and irons, for he had gone into the drain naked, he dragged himself up the ladder to his work. If his bruised and haggard condition was noticed, it excited no remark, the evidences of fighting and sleeplessness being too common among the wretched culprits to awaken any suspicion.

A few nights after this, having recovered somewhat from the sufferings he had incurred, it was judged practicable to complete their escape, and Henry and a few others made preparations to leave. Among these was a man named Prescott, of New Haven, who had been sentenced to the prison for smuggling. David Wooster and Doolittle seem not to have participated in the attempt, for whatever reason is not known; possibly being unable to extricate themselves from their fetters sufficiently to warrant the attempt. It was an hour before day when Henry and his associates broke through the remaining portion of the drain and and into the woods. Their escape was soon discovered and the alarm given. Those of the others were retaken and conveyed back to prison. Henry, more fortunate, concealed himself in a dark hemlock growing on the mountain, until the next night, when he began his flight, and finally succeeded in reaching the coast at or near New London, and made his way on board an English vessel, where he enlisted in the British service,

Not long after this a general plan of insurrection and escape was carried through successfully. About ten o'clock at night, May 18, 1781, when all the guard but two had retired to rest, the wife of one of the prisoners applied for permission to visit her husband in the caverns. This was not an unusual thing then, and her request was granted. The trap-door being raised to admit her, the prisoners, who by arrangement had gathered upon the ladder, prepared for the encounter, instantly sprang through, snatched the guns belonging to the two men on duty, and made themselves masters of the guard-room before the rest of the guard could be aroused. One of the officers, named Sheldon, learning the state of affairs, made a desperate fight; but the brave fellow was stabbed by a bayonet and died in a few minutes. The other soldiers, after a short struggle, were overcome, a few fled and the remainder were thrust by the prisoners into the caverns and locked in. The prisoners, twenty-eight in number, it is said, all escaped, and being now well armed most of them avoided a recapture.

Such is the statement given in the History of the Prison. Either, however, there is some error in it, or else David Wooster and Samuel Doolittle were among those retaken, for it is certain that after this they were still in confinement. About a year later we find on the records of the legislature an entry as follows:–

Upon the petition of David Wooster, Jr., showing that being very young and under the influence of John (Alexander) Graham, a deserter from the Continental army, and some others of much more respectable connections, he was induced to be concerned in the villainous conduct of plundering the house of Ebenezer Dayton, of New Haven, and afterward of going over to Long Island, and soon after of being retaken and brought back, for which be was sentenced for confinement in Newgate Prison for the term of four years, of which be has already suffered almost two years, and asking that on giving sufficient bonds for his good conduct hereafter, be may be released from prison, and permitted to enlist as a soldier in the Continental army, etc.

Therefore, be it resolved by this Assembly that upon getting sufficient bonds to the amount of £150 that he will be of good behavior hereafter, be shall be liberated and permitted henceforth to live in some town in this state on the east side of the Connecticut River, under the oversight and control of General Spencer.

Subsequently be was released from his bond and allowed to return home, under a permit from that officer.

Doolittle made a similar petition about the same time, which, however, was refused. In January, 1783, he renewed his application with better success. It was ordered that upon giving his note to the state for the payment of all costs incurred, be might be released from prison, and allowed to reside in the town of Woodbury, under the care of the selectmen of the town, for the remainder of his term.

Seeley and Wooding obtained also some abatement of their respective sentences. In fact, as the war was visibly drawing to a close, the dangers resulting from disaffection to the country diminished, and the feelings which had been cherished against it were much softened. The estate of David Wooster, having been confiscated, was, after a few years, placed in the care of the town of Waterbury for the support of Wooster's children, two of whom, as we have before stated, were imbeciles. It is believed that subsequently it was restored to the family. Till within a few years past it has been occupied as a residence by some of his descendants. One of his sons was known to the writer as a preacher in the Methodist church, and another. James D. Wooster, Esq., as a highly respectable citizen and magistrate.

Four years after the termination of the war, a traveler, one day in the dusk of evening, came to the house of Henry Wooster, Sen., in Derby, and asked permission to lodge there for the night. He was weary and footsore, he said, and could go no farther. Hospitality in such cases was a habit of New England, and his request was granted. Mrs. Wooster was then engaged in preparing a kettle of hasty pudding for the family supper, and at her invitation the traveler partook of the repast. In the course of it he contrived to turn the conversation upon the subject of her own family, and especially of her absent son. She recounted with a mother's partiality his amiable qualities, his manly agility and strength. Won by the interest he seemed to manifest in her story, she bewailed the sad occasion of his falling in with a stranger, who had persuaded him to go off on a mad undertaking of revenge on a piratical Yankee captain, in consequence of which he got into prison. After a while he broke out with others, since which she had heard nothing from him, and presumed he must be dead.

At length, when he had sufficiently drawn forth the reminiscences of the good woman, the traveler assumed his natural speech and manner, and announced himself as her missing son. At first she was incredulous, and unable to recognize him, till, opening the bosom of his shirt, he showed her a mole on his breast. This well-remembered mark convinced her of his identity. She fell on his neck, and, like the father of the prodigal, wept tears of joy over her long-lost boy.