Research on bikesharing has largely focused on systems operating in large cities. Based on the Swiss experience, this paper explores the challenges that small cities (<100,000 inhabitants) face in implementing such systems. It presents four types of evidence: (1) historical evolution of bikesharing in Switzerland; (2) current configuration of the systems; (3) usage rate; and (4) strategies and policy choices. Results show that the challenges in terms of usage rate and economic sustainability of bikesharing systems in small cities are considerable. The density of bikesharing networks, the existing modal share for each city, and possible target groups are elements that must be taken into account to improve the performance of bikesharing systems. The Swiss experience also suggests that the ability to develop partnerships as well as communication and accountability play a critical role.