In November 1904 telegraph service was extended to Headingley, but were still missing modern conveniences of a streetcar and voice telephone service. In the early part of the 20th century, an interurban train, Route 29, operated by the Suburban Rapid Transit Company, Manitoba served the Headingley area, but this line was discontinued in the 1930s. The Headingley Correctional Institution, a provincial jail, holds 549 inmates. It was built in the early 1930s. After the interurban cars stopped service, a diesel bus service was implemented. In the route numbering of Winnipeg Transit routes since June 1984, route 81 Headingley was the bus that serviced the area. In 2013 the Manitoba government decided to divide a 1.7 kilometre section of the Trans-Canada highway that runs thru Headingley because it was notorious for vehicle accidents.
Secession from Winnipeg
Initial discussions about Headingley seceding from Winnipeg started in March 1987. From January 1, 1972 until December 31, 1992, the Municipality was part of the City of Winnipeg. A Referendum was held on November 14, 1991 asking Headingley residents if they wanted to break away from the City of Winnipeg. It seceded from the larger city in 1993 after extensive complaints that the local needs of the mostly rural community were not being met as part of a large urban city. They were not receiving water, sewage, access roads. Headingley residents wanted the City and Province to spend $4 million on extending water services to the community. As a result of the breakup, it is the only municipality besides Winnipeg in Statistics Canada's Manitoba Census Division No. 11.
Water
The Cartier Regional Water Co-op manages the water supply to the R.M. of Headingley, as well as several other nearby Rural Municipalities such as Cartier, Rosser, Macdonald. The Headingley Water Treatment Plant is one of two operated by the Co-op. The other is located in the R.M. of Carttier. Intake source water is from the Assiniboine River via a pipe. It is then moved to a facility on the site of the Headingley Correctional Centre River Intake Building where debris and silt are removed.
Local businesses
Local businesses located in Headingley include T&T Seeds, Shelmerdine's Nurseries, Flying J, The Gates on Roblin, and Taillieu Construction.
Community Centres
Headingley has two community centres. The older Phoenix Community Centre, and the newer $1.8 million Headingley Community Centre.
