Aim The current study aimed to assess the frequency of helmet use in a sample of Greek motorcycle riders as well as identify factors affecting self-reported helmet use including the riders’ motivations and various socio-demographic, environmental and trip-related characteristics. Method A probabilistic, stratified random sampling was performed to select 405 riders aged 19–65 years from three cities of Crete. Data were collected through an easy-to-use self-administered questionnaire during face-to-face contacts with the study participants. Results The overall self-reported helmet use was very low. Gender, years of education, consumption of high concentrated alcohol, and time of day when riding occurred, were significant predictors of the frequency of self-reported helmet use. High agreement with the factors of Imitation (B = 5.4, p < .001), Experience (B = 2.6, p = .001), Self-protection (B = 3.8, p < .001), Environment (B = 5.8, p < .001), and Regulation (B = 4.2, p < .001) as well as low agreement with the factors of Discomfort (B = −4.3, p < .001) and Underestimation of danger (B = −1.9, p < .013), were associated at a statistically significant level with higher frequency of self-reported helmet use.