A system including a computing device may receive base map information, including attribute information associated with a plurality of road segments, and trip request information. Based on this information, a route for the user to travel may be determined. The system might further calculate a risk score for each road segment forming the route, and generate a risk map based on the risk score and the route. The risk map may then be displayed to a user. The risk map may include markers or other objects depicting potential risks along the route the driver may face. Also, the risk map may be updated based on information collected from a sensor coupled to the vehicle or located at the road segment to reflect actual, real-time risk scores calculated using an equation for providing a risk score for a particular driver driving a particular vehicle on a particular road segment.