Road safety is the result of the interaction between human, vehicle, and environment-related factors. Road familiarity, as a human- and environment-related factor in road safety, was investigated in the present study. More specifically, the main aim of the current study is to investigate the subjective risk evaluations of drivers on familiar and unfamiliar roads. A total sample of 479 drivers, 278 males and 201 females, participated in the present study, and filled out the demographic information questionnaire and Risk Perception Inventory. The results showed that drivers evaluated risk as higher when driving on an unfamiliar road as compared to driving in a familiar road. Moreover, females reported a higher risk perception level than males on both familiar and unfamiliar roads. As a result, familiarity with the road was evaluated as an essential factor in the risk evaluation of drivers. The results were discussed with regard to their implications for road safety in light of the relevant literature.