Winston Churchill Boulevard is a long north-south roadway that predominantly forms the western boundary of Peel Region with the eastern boundaries of Halton Region and Wellington County, in Ontario, Canada. The road begins at Lakeshore Road in the south at the boundaries of the City of Mississauga the Town of Oakville, and ends in Caledon at East Garafraxa-Caledon Townline. The road is named in honour of British Prime Minister Sir Winston Churchill.

The Regional Municipality of Peel is a regional municipality in the Greater Toronto Area, Southern Ontario, Canada. It consists of three municipalities to the west and northwest of the city of Toronto: the cities of Mississauga and Brampton, and the town of Caledon, each of which spans its full east–west width. The regional seat is in Brampton.