The earliest overland routes in Wisconsin were Indian trails, which often determined the route of the first roads. During the first decades of the 19th c. settlers widened many Indian trails into roads suitable for ox carts and wagons. By 1829, for example, lead miners had blazed several wagon roads through southern Wisconsin for hauling lead. Established Indian trails between Fort Dearborn (Chicago) and Fort Howard (Green Bay), and Green Bay and Prairie du Chien, were straightened by the military and local settlers for use as wagon roads.

Increase Lapham, in his Geographical and Topographical Description of Wisconsin... (Milwaukee: P.C. Hale, 1844) listed all the roads then in existence or under construction as follows: "Appropriations have been made by the general government, and expended on the following roads. From Green Bay, by Milwaukee and Racine, to the State line: distance, one hundred and fifty-eight miles. From Milwaukee, by Aztalan and Madison, to the Mississippi, at a point opposite Dubuque. From Sauk Harbor, on Lake Michigan, to Dekorra, on the Wisconsin river: distance eighty-six miles. From Fond du Lac, by Fox Lake, to the Wisconsin river. From Racine, by Janesville, to Sinipee, on the Mississippi: distance one hundred and fifty miles From Fort Howard, Green Bay, by Fort Winnebago at the Winnebago portage, to Fort Crawford, at Prairie du Chien, called the " Military Road" : distance from Fort Howard to Fond du Lac, fifty-six miles; thence to Fort Winnebago, sixty miles; thence to Fort Crawford, one hundred and nineteen miles."

"Hit the Road: Early Road Development" at Wisconsin History Explorer

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