The purpose of this study is to clarify the mechanism of traffic accidents involving cyclists. The focus is on the characteristics of cyclist accidents and scenarios, because the number of traffic accidents involving cyclists in Tokyo is the highest in Japan. First, dangerous situations in traffic incidents were investigated by collecting data from 304 cyclists in one city in Tokyo using a questionnaire survey. The survey indicated that cyclists used their bicycles generally while commuting to work or school in the morning. Second, the study investigated the characteristics of 250 accident situations involving cyclists that happened in the city using real-world bicycle accident data. The results revealed that the traffic accidents occurred at intersections of local streets, where cyclists collided most often with vehicles during commute time in the morning. Third, cyclists’ behavior was observed at a local street intersection in the morning in the city using video pictures. In one hour during the morning commute period, 250 bicycles passed through the intersection. The results indicated that one of the reasons for traffic accidents involving cyclists might be the combined effect of low visibility, caused by the presence of box-like building structures close to the intersections, and the cyclists’ behavior in terms of their velocity and no confirming safety. It was observed that, on average, bicycle velocity was 3.1 m/s at the initial line of an intersection. The findings from this study could be useful in developing new technologies to improve cyclist safety, such as alert devices for cyclists and vehicle drivers, wireless communication systems between cyclists and vehicle drivers, or advanced vehicles with bicycle detection and collision mitigation systems.