The town of Halton Hills shares jurisdiction with the Region of Peel over the segments along the Halton-Peel boundary between Mayfield Road and 32 Sideroad.

The remaining northerly segment between Beech Grove Sideroad and East Garafaxa-Caledon Townline is under joint jurisdiction between the Town of Caledon, Town of Erin and Township of East Garafraxa, where Winston Churchill forms the boundary between any two of these municipalities.

Formerly, this section also formed the divisional boundary, but was changed due to municipal restructuring in 1974 resulting in transferring of the lands to the west to Mississauga.

[3] In the community of Norval, Winston Churchill Boulevard deviates westward to be situated entirely within Halton Region and is known as Adamson Street.

[4][5] The Mississauga Transitway's western terminus, Winston Churchill Station is located just north of Highway 403.