Adolescents experience many benefits from bicycling; however, there are also potentially significant injury consequences. One effective countermeasure for the prevention of adolescent bicycling injuries is to promote bicycle helmet wearing. An overview is provided of injury risks of bicycle riding with particular attention to the role of helmet wearing and associated countermeasures such as legislation and school and community approaches. The findings are presented of a study conducted in Australia that examined the effectiveness of a theory-based injury prevention program, Skills for Preventing Injury in Youth (SPIY) for ninth-grade students (age 13 to 14 years). The findings showed a significant, 20.2% decrease in cycling without a helmet among the intervention students (n = 360) and no change for the students in the comparison group (n = 363) after 6 months. In addition, it was found that failing to wear a helmet was significantly associated with engaging in other transport-related risks, being mate, having friends who do not wear a helmet and are specific targets of change in the SPIY program, showing a negative attitude toward risk, failing to intervene in friends' risk-taking, and having low knowledge of first aid. Overall, the SPIY program appeared to be an effective theory-based intervention to increase helmet wearing among early adolescents, a group not often targeted in school and community helmet-wearing programs.