Changing socio-technical practices occurring within cycling are leading the pursuit, and its participants, to become ever more embedded into the networked digital world. GPS enabled mobile-technologies have introduced a new element of competition into recreational riding, whether on the road, competing over timed virtual segments, or online dissecting and comparing the data that has been logged and shared via dedicated ride-logging applications. In order to understand these technologies qualitative study using reflective diaries and semi-structured interviews has been conducted with experienced club cyclists who had fully experienced the effects of their arrival. These riders claim that the applications influence their route choice and motivate them to cycle more frequently, and at a greater intensity although the engagement changes over time. This paper explores how this increased motivation to exercise and compete is instigated, manifested and maintained in the everyday practices of cyclists, as well as the negative consequences of gamification.