Timothy Street’s roots in America go back to his 3rd great parents Rev. Nicholas Street and Ann Pole Waldron who arrived in Massachusetts in approximately 1635.
Very little is known of Timothy other than that he was born in Norwalk, Connecticut., and was the second son in the family. He went into partnership with his brother in Ridgefield, Connecticut in a venture connected to the fur trade.
He later settled in Spencertown, Columbia County, New York State. This area lies between the Hudson River and the Massachusetts border. Timothy’s wife’s family, the Lockwoods, was among the first settlers in the area. Spencertown was on the line of the old Indian trail between New York and Canada. He was likely still in the fur business, within easy reach of important trading centres. He would not have wished to jeopardize his dealings with the Six Nation Indians, strong supporters of England and most certainly would have been concerned with the freedom of trade routes during these unsettling times. In any case, Timothy was one of the Columbia Tories, and an adherent of King George III.
On June 15, 1777, he joined the Royal Yorkers. The life of a soldier was extremely hard in this area of the country and tested a man’s endurance and Timothy was not getting any younger. He was discharged on June 6th, 1778.
Following his discharge he seems to have possibly found other ways to serve the Loyalist cause. It is thought that he may have become a courier or a spy as he would have been familiar with the land, water routes and valuable acquaintances. It is said that spies followed a route through Spencertown and were harboured by Loyalists.
Street family tradition says that Timothy drowned in Lake Champlain. It is assumed it happened between his discharge and the end of the war in 1781. His sons’ petitions state that their father “died in His Majesty’s service during the late American War.”
By 1800, three of Timothy and Susannah’s children had traveled to Upper Canada and all three received land grants as being sons of a Loyalist. One of these sons, Timothy Jr., eventually became the founder of Streetsville, now part of the City of Mississauga.
Submitted by Gayle Waldie UE and Marsha Waldie UE