The route of the trail (and the bordering WIS 23) had been used as a footpath by Native Americans; later, the route was occupied by a plank road. The original approximately 17-mile (27 km) section from the city of Sheboygan to Greenbush was constructed over the course of 1977 to the early 1990s.[3]
Between 2019 and 2022, an approximately 17-mile (27 km) westward expansion of the trail into Fond du Lac County was constructed as part of a project to widen Highway 23;[4] 4.4 miles (7.1 km) of this length brought the trail to the Sheboygan County border.[1]