Intelligent transportation systems (ITS) have focused primarily on systems management. To improve connectivity and safety further, ITS might embrace a more holistic planning approach. Although the future of ITS remains an open question, ITS evolution is closely linked to the social, political, economic, legal, and environmental dimensions. This paper presents the results from four expert workshops: (a) initial steering committee workshop (February 2011), (b) two expert scenario-planning workshops (June 2011), and (c) a final steering committee workshop (July 2011). The scenario planning workshops explored the implications of alternative futures in ITS and incorporated a broad, interdisciplinary approach to develop a long-term transportation vision (2030 to 2050 time horizon) for the United States. Twenty-four experts, who represented diverse disciplines, participated in a series of workshops to envision plausible futures and to assess their effects on the transportation system. By exploring different futures, experts identified opportunities and barriers to the implementation of advanced, seamless transportation systems. Opportunities included the deployment of adaptable, integrated technology and transportation infrastructure to address natural disasters and climate change. The most significant barriers were funding and politics. The experts suggested that financial barriers could be overcome through the use of innovative funding techniques and improved public outreach. Several visions for an integrated ITS approach were then built on the experts' recommendations to address social and environmental challenges in the future. These recommendations included private–public partnerships, distributed implementation models (e.g., localized), and the development of seamless transportation systems to reduce energy consumption, emissions, and road congestion.