(red, with
Worcester County in pink) at various conventions. On January 5, 1775, Singletary was elected to be a delegate of Sutton to the
Massachusetts Provincial Congress in
Cambridge held on February 1. Later, on May 22, he was elected again, to a second congress in
Watertown on May 31. He was nominated to be a
justice of the peace on September 18 of that year, entering politics upon assuming the office. He and Willis Hall were elected May 19, 1777, to represent Sutton in the
General Court in the coming year. In the next decade, Hall became the chair of Worcester County conventions that hoped to influence the Court; Singletary served in the
House of Representatives in the 1781–82 and 1783–84 sessions, representing Sutton with Hall during the former. During the Revolutionary War, he was listed on a committee to train men in Worcester County to fight in
New York and
Canada, and as a legislator, he opposed
eastern Massachusetts policies that, in his view, tormented
western Massachusetts farmers. He was chosen on September 25, 1786, to be a delegate to a county convention in
Leicester to ask for the state capital to be moved out of
Boston. Many residents of western Massachusetts resented the influence of Boston elites over the state legislature, which they felt was taxing the Western region too heavily. This resentment also motivated
Shays' Rebellion, an armed uprising that had emerged that summer. The town of Sutton selected Singletary as part of a committee to try to mediate between active rebels and the state government, which had sent thousands of troops to suppress the uprising. The delegation managed to meet with General
Benjamin Lincoln, though the rebellion continued for many months more. ==Constitution Ratifying Convention==