The Federal Aid Highway Act of 1956 led to massive investments in highway construction, changed the nation’s physical landscape, and transformed how people traveled and where they lived. It also wreaked havoc on low-income and Black neighborhoods, imposing undeniable injustices, making no aid available to support residents displaced from their homes, and doing little to protect them from deleterious effects on air quality. This Article reviews events leading up to and repercussions flowing from the decision to build the Interstate Highway System, focusing on Black and low-income displacement and its repercussions in Baltimore, Maryland; Columbus, Ohio; and St. Paul, Minnesota. It reviews the impacts of the environmental justice movement on the federal government’s strategy and on the current regulatory policies of the Federal Highway Administration. The authors offer examples from Charleston, South Carolina, and Houston, Texas, that demonstrate the limits of federal leverage on road-building, and conclude with suggestions for moving forward.