Modern Mississauga and Heritage Mississauga have come together to present an ongoing series called “Way Back Wednesday’s."

We’ll share information about the history of Mississauga here and answer your questions.

Today’s topic is the history of Henry Street & Rutledge Road.

Henry Street is Streetsville is named for “Commodore” Henry Rutledge (1800-1875). Henry was born in Enniskillen, Ireland, and together with his father Henry Sr., his mother Ann, and his 9 siblings, Henry immigrated to New York State in 1815, before coming to Streetsville in c1820.

Henry was already married, to Jane Noble, upon his arrival in the Streetsville area in 1820. Their eldest child, Kate, had been born in New York State. Henry and Jane had seven more children: Leah, Mary Ann, Sarah, William, Eliza and Edward. Henry’s brother John also settled nearby, and together the families became one of the most prolific and influential families in southern Peel County. Henry is said to have named his farm north of Streetsville the “Queen’s Bush Hill”.

Henry donated land for Trinity Anglican Church and Cemetery and for the Orange Lodge in Streetsville. He also donated land for a school, and was a charter member of the Streetsville Farmers’ and Mechanics’ Institute. Over time Henry amassed over 300 acres of land at the north end of Streetsville, and became one of the most prominent in the early community.

Henry’s first wife, Jane, passed away in 1831, and he soon remarried Isse Arabella Lewis (1811-1862), and together they had 11 children: Joseph Jabez (1833), Cornelia (1836), James (1837), William Henry (1838), Esther (1838), Ellen (1840), Arabella (1844), John Christopher (1846), and three who died in infancy. In total, Henry had 18 children.

Henry is described as a “colourful character” and a “man of substance”. He not only operated a farm, but had a brickyard (many early buildings in Streetsville drew bricks from the Rutledge farm), but also served as a church warden, first for the Presbyterian Church, and later for the Anglican Church. Together with John Embleton, Henry was appointed as trustee of the first town hall and court house, built on Church Street. Henry was viewed as a figure of authority and responsibility, and he was also involved in local politics. Locally Henry was referred as “Commodore”, most likely in reference to his involvement with the Orange Lodge. While there is no known image of Henry Rutledge, several other streets in northern Streetsville are named for his children, including William, John, Joseph, Ellen and James streets, as well as Rutledge Road.