Problem: One hundred years ago the First National Conference on City Planning took place inWashington,DC. While in some ways the delegates failed to foresee future trends (such as the consequences of automobility and suburbanization), in other ways they were remarkably prescient. They stressed the importance of the transportation/land use link, understood that transportation facilities must be harmoniously embedded in the urban fabric, and viewed transportation investments as a tool that could be used to shape the city as a whole—directing growth, revitalizing flagging areas, and linking jobs and housing. This vision was kept alive by transportation planners in subsequent decades, who envisioned a network of urban freeways which would be context-sensitive and fully integrated into their urban milieu. However, due to a lack of local funding and control, these roads were never to be built and this vision was to be abandoned. Purpose: In this paper, we consider the history ofU.S.urban transportation planning over the past 100 years. In particular, we focus on the evolution and legacy of the single most important transportation development of the past century save for the advent of automobility itself: the emergence of the urban freeway. Methods: The paper relies on an historical review of primary and secondary material, including plans, manuscripts, newspaper accounts, and scholarly articles and books. Results and conclusions: The paper argues that financial arrangements placed state and federal highway engineers in charge of interstate highway development, which affected highways' location and design. State highway engineers imposed a narrower, traffic service-oriented vision on metropolitan freeways that focused on maximizing vehicle throughput; other urban concerns were largely ignored. After a desultory planning process, overbuilt, sparse, ring-radial networks were routed through neighborhoods in cities around the country, often with great social and environmental costs. Though the system has undeniably conferred great benefits in terms of enhanced mobility, the costs have been high as well. Recent years have seen a return to a more urban planning-oriented view of transportation that stresses the land use interaction and the social, environmental, and aesthetic impacts of transportation facilities. It is a vision with which the founders of what became the American Planning Association (APA) would have sympathized. Takeaway for practice: The paper highlights 100 years of transportation planning practice, and provides an accounting of ideas that have resurfaced in transportation planning since the early 1990s. The paper stresses a century-old vision of coordinated transportation-land use planning that has returned to the fore in practice today. The paper suggests that political expediency in public finance can have profound, long-lasting, frequently unanticipated effects on projects, travel, and urban form.