Cycling on the pavement is commonly seen in urban environments despite often being prohibited. This study explores this practice by analysing cycling on pavements in the wider socio-technical context in which it occurs. Using data from two field studies and one questionnaire study, as well as applying a Social Practice Theory (SPT) based analytical approach, the study explores the frequency of cycling on the pavement. The results show that riding on the pavement is common among cyclists. Three main configurations of meaning, material and competence constitutes this practice which is summarised as follows: avoiding the space of the car, increasing smoothness of the ride and unclear infrastructure design. Cycling on the pavement can be regarded as a way of managing safety and risk, seeking more efficient and comfortable paths of travel, as well as the outcome of perceiving the infrastructure as ambiguous. Overall, the study argues that cycling on the pavement is a consequence of skewed power relations between different modes of transport, as well as policies, urban planning and infrastructure not harmonising with demands for safe and smooth travel by cyclists.