During the second half of the twentieth century, the automotive strip emerged as an epistemological platform that allowed architects to document, explore, and theorize the increasingly unfamiliar form of the postwar city. Studies like The View from the Road (1964), Los Angeles: TheArchitectureArchitectureof Four Ecologies (1971), and Learning from Las Vegas (1972) employed radical empiricism to generate new understandings of the automotive landscape and, by extension, the automotive city. The following case study leverages these methodologies while reassessing the past, current, and future impact of automotive technologies on the strip. The case study specifically investigates the historical life of Fredericksburg Road–a heavily traveled arterial in San Antonio, Texas, USA. The research constructs a timeline of Fredericksburg’s growth, registering the strip’s shifting forms, programs, and narratives over 120 years and 12 miles. The exercise establishes five historical eras characterized by the streetcar, automobile, regional shopping mall, edge city, and lifestyle center. In this context, the research considers the transformative potential of more recent trends related to online shopping, shared mobilityMobility, and automated vehicles. Collectively, these developments promise to alter the strip’s form and program yet again, potentially putting vast amounts of square footage back into play. The chapter concludes by proposing a new narrative for Fredericksburg Road that advocates a smaller, slower, and more local future for the road. By pushing back on a century of modern road design, this alternative narrative resists the technocratic, commodifying interests that developed the automotive strip in their own image.