Historians of the nineteenth-century American Middle West typically pay scant attention to the financial and regulatory role that smaller cities played in forging a regional railroad network. This article, however, explores railroading in La Crosse, Wisconsin, to demonstrate that politicians and boosters in such cities often took advantage of municipal power to shape the course of railroads in unexpected ways. In 1853, 1864, and 1876, for example, local boosters convinced city aldermen to fund railways and help forge commercial links to Milwaukee, Minneapolis, Chicago, and other markets in the East and West. The city's influence over railroading did not start and stop with public investment. Beginning in 1883, after state lawmakers had amended the city's charter and given municipal officials new police powers, aldermen forced railroad executives to clear city streets, prevent damage to private property, and guarantee the personal safety of local residents. Moreover, even when La Crossers lost a fight with railroads, as they did when they waged a holy war over the location of a Mississippi River bridge in the 1860s and 1870s, they forced railroad men to pay attention to their concerns. In the end, the case of La Crosse suggests that historians need to pay much greater mind to people and governments in small, hinterland cities before they can fully grasp the rich history of railroading, and of capitalism more generally, in the nineteenth-century Middle West.