A History of Headingley

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Written by Jean Ammeter of the Headingley Historical Society

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The constituency of Roblin includes the rural municipality of Headingley. This area includes both sides of the Assiniboine River and is bound by the perimeter and Camp Manitou Road on the east, the R.M. of Rosser to the north, the R.M. of St. Francois Xavier and the R.M. of Cartier to the west, and to the south, Headingley is bordered by the R.M. of Macdonald.

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In its rural setting, Headingley has recreation for all ages. Headingley Community Centre, Phoenix Recreation and MacDonald-Headingley Recreation each have numerous programs and sports. There are many walking trails throughout the community including the Grand Trunk Trail which connects the Harte Trail to Beaudry Park. There are also many amenities such as Jim’s Vintage Garage, senior’s services, a 55+ Club, a 4-H club, and 2 golf courses that add much enjoyment.

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The R.M. of Headingley was formed in 1992. The municipal office is located on Bridge Road along with Headingley Fire and Rescue. Pheonix School is a Kindergarten to grade 5 school and belongs to the St. James- Assiniboia School division. There is a day care program, 4 churches, the Headingley Foundation, and a Chamber of Commerce. The Headingley Library adds much to the community.

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Headingley has a long and interesting history. It started as a farming community and remains rural today. The first permanent settlements started with churches in homes which the Anglican established in 1852 followed by the school in 1854 with John Taylor as teacher. In the beginning North Headingley was a part of Assiniboia’s municipality and South Headingley was part of Charleswood’s municipality which formed a connection over the years.