Watch on Soap2day. This 572-mile route connects some of the Midwest’s finest trails, quiet backroads, small towns, state parks, and the Mississippi River between Chicago, Illinois and Saint Paul, Minnesota. Along the way, it passes through Lake Geneva, Kettle Moraine, Madison, Devil’s Lake, the Elroy-Sparta Trail, La Crosse, Lanesboro, Mystery Cave State Park, Frontenac State Park, and the Twin Cities.