Introduction: An argument against mandatory helmet use is based on the idea of risk compensation, which means that cyclists might ride faster when wearing a helmet (Lardelli-Claret et al., 2003). However, questionnaire and experimental studies were unable to find evidence for this assumption (Fyhri et al., 2012; Fyhri & Philipps, 2013). Simultaneously, other factors with a potential role in helmet use and cycling speed, such as trip length and rider characteristics have been neglected in such considerations. The goal of the analysis presented in this paper was therefore to investigate the relationship between helmet use and cycling speed under naturalistic conditions while taking characteristics of cyclists and bicycles into account. Method: As part of a naturalistic cycling study, we equipped the bicycles of conventional and e-bike riders with data acquisition systems to record speed and trip distance. It included two cameras (one for the face of the participant, another one for the forward scenery). For the analysis presented in this paper, we used the data of 76 participants (28 conventional bicycles, 48 e-bikes). Results: In total, participants used their helmet for 56% of all trips. Helmets were used more frequently for longer trips. A linear mixed model, in which trip length, helmet use, bicycle type, age, and gender were used as predictors showed that helmet use did not play a significant role for cycling speed. Instead, all other factors that were analyzed, with the exception of gender, had a significant relationship to cycling speed. Discussion: The assumption of risk compensation as a result of the use of a helmet could not be confirmed. Instead, the findings seem to support the suggestion that cyclists who undertake trips at potentially higher speed levels are aware of their increased risk, and actively try to reduce it through the use of a helmet.