Urban cycling is a sustainable transport mode that cities currently try to expand. However, cities still do not take advantage of geospatial technologies to understand cycling mobility based on the behavioural patterns and difficulties faced by cyclists. This study analyses a geospatial dataset crowdsourced by urban cyclists using an experimental geo-game. About 20 participants per city recorded bicycle trips during one week and, by aggregating them, we found not only the cyclists’ preferred streets but also the frictions faced during cycling. We successfully identified 284 places potentially having frictions: 71 in Münster, Germany; 70 in Castelló, Spain; and 143 in Valletta, Malta. At such places, Participants not only recorded bicycle trips but also segments at lower speeds indicating a deviation from an ideal cycling scenario. We described the potential frictions preventing from bicycle commuting based on the distance to bicycle paths, surrounding infrastructure, and location in the urban area.