The Green Bay Trail has historical significance dating back nearly 12,000 years, when it is presumed that woolly mammoths traveled along it for migration during the Ice Age.

The path started from Chicago across two different routes: one starting from the current Michigan Ave. bridge north on what is now Rush Street and through Chicago Avenue in Evanston, and an alternate route running northwest to where Clark Street and North Avenue intersect today.

The trail began its modern-day service in 1836 when stagecoaches were used to carry passengers from Chicago to Green Bay with intermediate stops.

The Shore Line was abandoned in 1955; the right-of-way was then leased to the Green Bay Trail Committee for development.

[11] Most of the rail trail is paved except for the portion between the Highland Park Metra station and Glencoe, which is primarily crushed stone.

[17][18] Volunteer beautifying projects including flower and vegetable gardens alongside the trail are also popular.