The unique new “smart bridge” which is computer monitored, was named for the Hon. John Taylor, who was a prominent Headingley landowner, as well as a member of parliament who played a role in the Louis Riel uprising.

The community of Headingley was founded in 1853 when the Archdiocese of Rupertsland acquired two River Lots from the Hudson's Bay Company for the purposes of erecting a church and a school. In 1854 the first Holy Trinity Anglican Church was built and it was named after the church in Headingley, Leeds, England, which sponsored the construction. The early pioneers were primarily from the British Isles.

Until the 1960s, Headingley was part of the Rural Municipality of Charleswood on the south side of the Assiniboine River and the Rural Municipality of Assiniboia on the north side. In 1972 the City of Winnipeg was restructured and Headingley was included in a newly aligned city boundary. From 1972 on, the City maintained a development freeze in Headingley. The City of Winnipeg consistently under-serviced the community despite the substantial amount of tax it collected from the area. Discontent with the lack of value for their tax dollar, the residents began a movement aimed at separating Headingley from the City of Winnipeg. This movement was successful and in May of 1993, Headingley seceded from the City of Winnipeg and became an independent municipality.