Travel behavior is undergoing a period of significant change in the United States. In 2016, public transit ridership fell in almost all major U.S. metropolitan regions. While Americans are still heavily dependent on the personal automobile for mobility, technological and societal changes are transforming how mobility is accomplished. This paper reviews the convergence of five trends leading to fundamental changes in public transportation: (1) changing generational behavior toward suburbanization and automobility; (2) new attitudes toward information communications technology; (3) shifting attitudes toward sharing and mobility on demand; (4) innovative alternatives to work and non-work travel; and (5) an increasing number of on-demand flexible route transportation options. The paper concludes with recommendations and guiding principles for public agencies to consider in responding to these trends.