In 1776, Wooster was appointed a major general in the militia of Connecticut in the American Revolutionary War. Wooster had supervisory control of all military supplies that were stored in houses near the town of Danbury. General Tryon of the British army planned to attack Danbury in order to capture Wooster's supplies. On April 27, 1777, Wooster attempted to head off General Tryon's advance in the nearby town of Ridgefield, Connecticut. Wooster attacked Tryon's forces with 700 new recruits but Wooster was forced to retreat.
Being inexperienced militia, and the enemy having several field-pieces, our men, after doing considerable execution, were broken and gave way. The General was rallying them when he received a mortal wound. A musket ball took him obliquely, broke his back-bone, lodged in his stomach and could not be extracted. His sash was spread out as a blanket and Dr. Turner dressed the wound in the field. Wooster was then carried from the field to a waiting carriage and slowly transported him to Danbury. He was taken to the Dibble house on South St.
A doctor came from New Haven to attend to Wooster. His wife and son arrived from New Haven only to watch for 3 days as he suffered in agony until overcome with unconsciousness. He died on May 2, 1777. on April 27th, 1852, his remains were taken from Wooster St. Burial-Ground, and placed in Wooster Cemetery.
5 days after to mortal wound, on May 2, 1777, Wooster succumbed to the fatal shot. Wooster's finals words were, "I am dying, but with a strong hope and persuasion that my country will gain her independence."