The rail line was built by Hiram Walker to connect his distillery in Windsor to Kingsville in 1882 and was extended to Leamington in 1889.

[citation needed] In exchange for naming rights, Chrysler Canada provided a $250,000 donation to convert the rail line to a bike trail.

[citation needed] The remainder of the rail line would also be abandoned, and its tracks removed to where they branch from the mainline between Highgate and Muirkirk.

[citation needed] The 1998 ECRA budget included $406,000 to develop the Chrysler Canada Greenway, part of which came from the sale of ravine land.

The trail starts at the junction with Kings Highway 3, with signs to cross at the nearby Walker Road due to the dangerously high levels of traffic.

The Municipality of Leamington has expressed interest in converting their abandoned rail lines east of Talbot Road (CR 34) into an extension of the Greenway.

The City of Windsor has also expressed its intentions on linking its bike trail network to the Chrysler Canada Greenway.