Methods, computer-readable media, systems and apparatuses for determining a safest road segment for traveling between a first location and a second location are provided. In some cases, the road segment safety rating may be determined for a plurality of road segments between the first location and the second location based on historical data associated with the road segments (e.g., accident history data, traffic volume data, etc.) and/or based on driving behavior data of the operator of the vehicle. An indication of the road segment determined as being the safest may be provided to the operator of the vehicle. An actual route of travel of the vehicle can be captured and compared to the safest route. If the vehicle has traveled the safest route, the operator may earn an award. If not, the operator may be notified that an award may be earned when an indicated safest route is traveled.