Physical improvements to a transportation network or policy actions such as toll decrease can have an impact on the environment by reducing the time and monetary costs of travel, which can work to enhance the attractiveness of surrounding land to developers, residents, and businesses. A proposed toll discount on the Chesapeake Bay Bridge-Tunnel connecting the Hampton Roads metro area with the rural Eastern Shore of Virginia was analyzed for its potential to influence land use and affect the environment. How practitioners can couple well-established technical assessment methods in various disciplines with public involvement and strategic planning to promote a comprehensive vision of the future for a rural area on the fringe of a growing metropolitan region was illustrated. Current conditions, assets, needs, goals and potential impacts were assessed in several key areas of interest to Eastern Shore residents: transportation, tourism, economic development, agriculture and aquaculture, natural resources, and quality of life (livable communities). The impact assessment examined the potential for effects attributable to toll reduction scenarios in each of these six topic areas. The assessment techniques included interviews, comparative case research, analysis of present and potential future regional development and commuting patterns through the application of a gravity model, and extensive public involvement in the form of public meetings and topic workshops. As a complement to the impact assessment, the study team formulated strategies and actions to manage future growth and development that could be anticipated with or without a reduction in the toll.