Growing consensus on the advantages of cycling has led policymakers to become more interested in increasing the share of bicycle commuters. Even though the bicycle’s popularity as a convenient transport mode declines with increasing distance, in recent times efforts are being made to increase the cycling distances as it may bring incremental benefits to society as a whole. As a basis to facilitate cycling for longer distances, this literature review aims to improve knowledge on what stimulates bicycle commuting beyond 5 km, by analysing both socio-psychological and physical factors. Perceived trip benefits, cycling habits, bicycle-friendly infrastructure, and e-bike usage were identified as key factors. In particular, the emergence of the e-bike could popularise bicycle commuting beyond short distances, as it has the potential to overcome physical barriers and to substitute cars for moderate trip lengths. This review also emphasises the relevance of encouraging people to cycle longer distances and discusses different tailored intervention strategies. However, further research is required to fully understand the dynamics of bicycle commuting beyond short distances. This study suggests a re-evaluation of bicycle infrastructure and technology, bicycling attitudes, and long-term behavioural change in differing (social and physical) environments, recognising that the actions identified as successful to this end vary across cycling cultures.