Oxford’s Notorious Tories of the Wooster Family

When the American colonists and the British were just beginning their long struggle, there was a great division of American sentiment; there were strong pro-British feelings in this area. These feelings often collided with the patriot fever that was beginning to be felt in this area. This division of belief - this difference in patriotic loyalties - led to many conflicts, even among family members.

The differences between the mother country and the colonies broke up a family-type relationship between England and her settlements in the New World. The bitterness of the struggle between Loyalists (Tories) and Patriots often split families in the colonies. The Wooster family of old Derby included both Tories and Patriots. (See article on patriot Gen. David Wooster at .) 

Other parts of the family tree were involved in the Tory side of that struggle. Lt. Thomas Wooster was an uncle of Gen. David Wooster. Among Lt. Thomas Wooster's eight children were five brothers, who were all Tories.

One of them, Capt. John Wooster, was born in December 1719. This Wooster was known as captain for his role in the local militia and not for service in the colonial armies assembled against the British.

Capt. John was in business with other area men who set up a fulling mill (where local farmers brought their wood to be cleaned and washed before carding and spinning). They also set up a sawmill and an early gristmill. Later they manufactured scythes and had a general blacksmithing business.

At the time of the Revolution, Captain John Wooster lived at the corner of Park Road and the Oxford Turnpike, now known as Route 67.  He lived in an old house that was a popular tavern, known as the Captain John Wooster Tavern.

Park Road got its name from one of Capt. John Wooster's idiosyncrasies. Capt. John owned a special wildlife area in which he alone could hunt deer. It was called "The Park." J.W. Barber wrote in his 1838 "Historical Collections," of the park. He said:

"About one mile and a half south of the center is the 'Park', formerly a place for deer. . .  A Mr. Wooster owned and enclosed about one hundred acres of land for the purpose of keeping deer. It is said that he had the exclusive privilege by law of restraining any person from hunting deer in the limits of  'the park.' Upon the outside of part of the enclosure, there was a kind of precipice, from which the deer, when pursued, would sometimes leap into the enclosure, much to the mortification and disappointment of unprivileged hunters."

Captain John owned several slaves throughout most of his life in Oxford, usually keeping a couple and one or two others to help run the tavern. Slaves were not too unusual in Oxford, but they were generally a possession restricted to the wealthier classes. It seems that the town folks did not take too kindly to Capt. John's Tory proclivities; perhaps they resented his wealth. For whatever reason, the townspeople of Derby met at a town meeting in January 1781, and voted to authorize and direct the selectmen to give Capt. John Wooster a certificate to free and emancipate his "Negro men," on the condition that they enlist in the state regiment for the term of one year.

Since Capt. John was known for his British sentiment, it seems unlikely he would have willingly given up his slaves to fight in the Colonial Army. The townspeople seemed more eager to have the Negro men serve in that army than Capt. Wooster was to have them leave.

Capt. John's brothers with Tory interests were:

• Henry Wooster, Sr., who lived about a mile south of Whittimore Tavern in Seymour
• Thomas Wooster, who also operated a local tavern, just across the road from his brother’s at Park Road
• Daniel Wooster of Derby
• David Wooster of the area known as Gunntown, which was at one time part of Oxford and was later included in Naugatuck, near the Oxford line

The brothers Henry and David each had a son named after them. These two sons, who were cousins, were among the band that took part in the locally notorious Chauncey Judd kidnapping.

Next week, this series will continue with a brief outline of the Chauncey Judd kidnapping. This young man was kidnapped during a robbery staged by area Tories, as revenge against a Woodbridge patriot who had been raiding British-controlled New York State. The kidnappers took the young man prisoner. They attempted escape through Oxford but were captured by local patriots. 

The story was the basis of a novel published in 1874 by Israel P. Warren and published by Perry Press of Naugatuck. The full-length book (now available online at http://www.our-oxford.info/military/Revolution/c_judd-book-text/Chauncey%20Judd.html) will soon be available as a Kindle Ebook, available for download at http://www.oxford-historical-society.org and at Amazon.com.