The safety bicycle arrived in the U.S. South in the middle of a transition from relative African American freedom following the Civil War to a reassertion of white hegemony in the region. This article examines how white and African American southerners interpreted the meanings and practices of the safety bicycle through a contingent spatial and mobility politics found at the intersection of race and technology. For African Americans, the bicycle was both a symbolic and real opportunity to express modern freedoms at the moment those freedoms were being curtailed. The South, however, was not the only region of the world where the politics of race shaped bicycle mobilities, and this article points to the ways the southern experience of bicycle technology mirrors but does not necessarily replicate places beyond the United States.