Two hospitals in two major German cities documented 543 injured bicyclists arriving at the emergency departments. Head injuries and crash circumstances were of particular interest. The latter information, like type of crash, type of bicycle and estimated cycling speed was mostly self‐reported. Injuries to the head and face were present in 239 bicyclists. 77 % received only AIS 1 injuries consisting of soft tissue injury, cerebral concussion and minor facial fractures. Nearly 10 % sustained AIS 3+ head injuries. Cyclists with head and face injuries tended to be older than the control group without head injuries, were involved more often in collisions with motor‐vehicles and were cycling faster. Single‐vehicle crashes represented more than half of all bicycle crashes that resulted in head trauma. Age and type of crash were associated with head injury severity. Helmet rate was 17 % among cyclists without and 18 % among those with head injury. No AIS 3+ head injuries were seen in helmet‐users. Analysis of the location of head soft tissue injury and helmet damage indicated that most contacts occur in the frontal and fronto‐temporal region of the head.