Cycling is a major global sport, which has strong broad appeal as both a participation activity and as a spectator event. Further to this, the sport itself is greatly interesting as a focus for academic investigation due to its pluralised and fragmented nature, meaning that it would be naïve to consider cycling to be entirely homogeneous. Critically, this allows cycling to be viewed via both modern and postmodern perspectives, and in particular the theory of liquid modernity provides a valuable angle for exploring the sport’s value and place within society. Within this chapter we make use of these perspectives in order to provide an appraisal of the development of the sport through a focus on three particular formats of cycling; road cycling, mountain biking and BMX. What this demonstrates is that the various formats of cycling demonstrate differing characteristic natures, which have been shaped by the eras into which they have emerged. In this respect we conclude that cycling has been fundamentally conditioned by both modern and postmodern influences, which thus contribute to the differences which are apparent across the various formats within the sport.