Many of us tend to forget that during the American Revolution the citizens of what was to become our nation were sharply divided. The Tories remained loyal to the King of England and wished to retain their status as colonists while the Patriots wanted freedom from the tyrannical rule of England and to form an independent and sovereign nation of their own. Often Tories and Patriots were neighbors which led to much unrest. Many acts of what we would consider terrorism today occurred on both sides.
Our community of Naugatuck was no different from the rest of New England in this respect. As the War for Independence dragged on tempers grew short on both sides with people believing that acts of robbery, vandalism and even murder were justified in the name of the cause.
It was into this violent world of conflict that a sixteen-year-old boy walked one dark night back in March 1780. Chauncey Judd was the son of a prosperous farmer, Isaac Judd, who lived in the Buck’s Hill section of Middlebury. He was courting a Naugatuck girl by the name of Ditha Webb and was returning home through the woods after escorting Ditha to a quilting bee.
The ancient house where they had been, stood until just a few years ago at the intersection of Webb Road and Rubber Avenue Extension. It is gone now but the remnants of an old retaining wall can still be seen along the road in this location.
Chauncey was taking a shortcut through the woods in the area of what is now Naugatuck’s open space preserve when, much to his misfortune, he stumbled upon a group of armed men. Startled, he wondered what they were doing in the woods so late at night but it was too late for him to hide as they had already seen him.
As it turned out this was a band of Tories who had just robbed the home of Captain Dayton, in Bethany, who was a Patriot and away on business in Boston. They had held Mrs. Dayton, her three children and two servants at gun-point while they looted the home and were now heading to the farm of Jobanna Gunn on what is now Gunntown Road to spend the night hiding out in his barn.
Unfortunately for young Chauncey, he recognized one of the men as David Wooster a young Tory neighbor. This sealed his fate as the group felt they could not let him go for fear of being identified. They dragged him along to the barn where they would spend the night.
The leader of the group was a bloodthirsty man by the name of Graham. He and certain other members of the band wanted to kill Chauncey but others in the group didn’t want to commit murder. You can imagine the fear and dread that young Chauncey must have felt while crouching in that cold barn as his captors argued his fate. To further terrify him, from time to time one of his tormentors would come over and kick or punch him just for the fun of it.
It was decided that rather than killing him they would take Chauncey to the Wooster house in Middlebury. There they would lock him in the milk room. Upon arrival they discovered that Captain Dayton, who had returned early from Boston, and a band of Patriots had traced the group to the Wooster house. They hid in a fruit cellar while nearly suffocating Chauncey to keep him from calling out for help as Captain Dayton searched the house from top to bottom.
The robbers then took Chauncey to David Wooster’s Tavern where they sat in the dark to talk things over. They decided on a desperate plan to head for Derby Landing, get a boat and go down the Housatonic River and across Long Island Sound to British held Long Island. A slave by the name of Tobia, who had been very badly treated by the Woosters, overheard the conversation and fled to get help. However, by the time that Captain Dayton arrived the thieves had fled.
Dragging their captive with them they arrived at Derby only to find that the only boat available was a somewhat leaky whaleboat with only four oars to propel it. With Captain Judd, Chauncey’s father, and a group of Patriots in hot pursuit the race was on. Chauncey hoped that his father would catch up but wasn’t at all sure if the leaky boat would sink or his kidnappers kill him first.
They landed on Long Island in the town of Brookhaven. Believing that they had escaped they hid their boat and ran to nearby Bailey’s Tavern. No sooner had they sat down than, much to Chauncey’s relief, Captain Judd and his men burst into the room. Too tired from rowing and bailing the Tories could not put up much of a fight. They were easily captured and a bleeding and exhausted Chauncey was reunited with his father.
Graham, the leader of the Tories, was ultimately hanged as a traitor and the Woosters spent four years in the infamous Newgate Prison for their part in the crime. The rest of the band was heavily fined but allowed to go free. As for Chauncey, he received the sizable sum of $4,000 compensation possibly from money and goods confiscated from the Woosters and other Tories. His health was never the same and he complained for the rest of his life of his treatment at the hands of his kidnappers.
He died at the relatively young age of 59 but not before marrying twice and fathering ten children. Today you can find his final resting place in Naugatuck’s Hillside Cemetery. It stands as a silent reminder of a long ago adventure and of the many interesting stories that make up our community’s long history.