This article reconstructs the historical transformation of mobility in the city of Maastricht in the period 1950–1980, from cycling as the most popular mode of traveling in the 1950s to car driving by the end of the 1970s. Based on an analysis of written sources and oral history interviews with Maastricht travelers and other practitioners who experienced this shift themselves, this article sheds light on this historical transformation, its key actors, and its main drivers. Combining insights from studies of social practice-based perspectives on mobility, historical sociotechnical transitions, and the model of urban obduracy, this study seeks to contribute to understanding why and how cities may transform toward being unsustainable places. Furthermore, it aims to show how social practice approaches can give more context-sensitive insights into processes of transformation and transition compared to established MLP-based transition approaches, by giving more attention to local meanings.