As Boscobel grew as a shipping point for regional products, a dependable crossing of the Wisconsin River became an economic necessity. The city was incorporated in 1864 so it could issue bonds to build a bridge, and in 1871 the Wisconsin legislature authorized Boscobel to bridge the river and collect tolls. Between 1874 and 1875, a 700-foot timber and iron bridge was built at a cost of about $26,000, and sometime after completion parts of it were covered. In 1935, as automobile travel had made the old bridge outdated and unsafe, the Wisconsin Legislature set aside funds for a new bridge at Boscobel. The State Highway Commission prepared plans for a 1209-foot bridge with seven Parker overhead truss spans and a simple concrete girder at the north end.