There's a rich history to this line. The Winona & St. Peter Railroad built out of Winona, reaching Stockton, a distance of eleven miles, by December 1862. That milestone earned it the distinction of being the second railroad operating in Minnesota. Construction continued westward, with the line extending to St. Charles in 1863, then eventually on to Rochester, Owatonna, and Waseca. The topography among the eastern Minnesota bluffs is challenging; it's difficult to imagine the crews of 1863 digging and blasting through the rock to put the track up here on the ledge above Garvin Brook.

In 1867, the Chicago & North Western acquired control of W&SP, and finally absorbed it into the C&NW system in 1900. In September 1986, the line was spun off to become part of the Dakota Minnesota & Eastern. Canadian Pacific assumed control of DM&E on October 30, 2008, and continues to operate the line today.