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General David Wooster was born on March 2, 1710-11 to Captain Abraham Wooster and his wife Mary. He was born at Oronoque in Stratford. About 1719, when David would have been eight or nine years old, the family removed to the Quaker Farms area in what is now Oxford. His family occupied a building known as the Mansion House. It was located near Munson's Corners and sold to Samuel Wooster, Jr., with a farm and saw mill, in 1733. At that time David Wooster would have been about twenty-two years of age.
In view of the fact that David Wooster graduated from Yale in 1738, it would appear that most of his life prior to attending the college in New Haven, was spent in the Quaker Farms area in Oxford. The year after he graduated he joined the provincial army. In 1745 he was a captain under Colonel Burr at the capture of Louisburg. Later in the French War, he was commissioned colonel and later brigadier of the colonial militia. After the war he went into business at New Haven.
Wooster also had an opportunity to visit Europe as a result of the French War. He was given the responsibility of a cartel ship bound for France and England. He was not allowed to land in France, but received a friendly reception in England.
He was presented to the King and is said to have been a favorite of the court and of the people. He was given a captaincy in the English regiments, with half pay for life.
Returning to New Haven, he became the Royal Collector of Customs at the Port of New Haven, which provided further income in addition to his captaincy and his merchantile efforts. However, his business began to fail, and he was in financial difficulties at the outbreak of the American Revolution.
He was sixty-five years old when the Revolution got underway. He was appointed Major General of six Connecticut troops in 1775 and recruited from the New Haven County areas. He marched these men to New York and encamped at Harlem. During the summer he also commanded troops on Long Island, whose duties were mainly guarding the livestock.
There was some trouble concerning promotions by the Continental Congress when it began to commission Generals. Wooster was named a brigadier General and some of his junior officers were given a higher rank. He was especially
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