Benjamin was born the son of John Whitear Sr. He was a successful bell founder, clockmaker, a warden of his church and an important and respected citizen. John Sr. had seven children, but because of the burning of Fairfield by the British under General Tryon in 1779, little information is known. In this fire, records of the Trinity Church were lost. It is thought that Benjamin worked as early as 1770 through approximately 1800. On May 15, 1764, he did marry Sarah (Beers) Buclkley. He is recorded in Norwalk in 1768 and then in Sharon in 1774. It is likely he was taught the trade of clockmaking by his Father John Sr.