This paper charts the distinctive challenges of designing mobile experiences for cyclists and presents two studies of mobile cyclebased experiences: one a heritage tour; the other an exploration of a city at dusk involving recording and listening to personal stories. and observations are drawn on to derive eight lessons for designing cycle-based interaction including: cycling proficiency, physicality, impact of the environment, media and hardware design, collaboration, and safety. The conclusion is that design has to respect the distinctive nature of cycling as a mode of transport and needs to carefully interweave moments of interaction with it. Categories and Subject Descriptors H.5.3 [Information Systems] Group and Organization Interfaces Collaborative Computing. General Terms Documentation, Design, Experimentation, Human Factors Keywords Cycling, bicycle, safety, mobile applications, tours, audio