Capital Bikeshare, one of the most successful in the nation, faces the challenges of a maturing system. Collaborating with DDOT, we developed Capital Bikeshare’s first strategic long-range plan for the Washington, DC portion of Capital Bikeshare. The plan, completed in time for Capital Bikeshare’s five-year anniversary, serves a guide for making future system expansion decisions. Foursquare ITP worked with DDOT to identify goals and objectives for the program and develop a performance monitoring plan. Our market study identified how the program was succeeding and where it was falling short in meeting its objectives. Based on these findings, we tested expansion scenarios using a customized tool we built for DDOT. Ultimately, the team developed a six-year expansion strategy for bike share, including DDOT’s first multi-year financial and ridership model forecast.