An obstacle detection and notification system for a motorcycle. The system includes a forward looking camera and a backward looking camera mountable to the motorcycle and a processor in operable communication with the forward looking camera and the backward looking camera. The processor executes program instructions to execute processes including: receiving video from the of the forward looking camera and the backward looking camera, performing a computer vision and machine learning based object detection and tracking process to detect, classify and track obstacles in the video and to output detected object data, defining a blind spot region around one or more other vehicles using the detected object data, determining whether the motorcycle is located in the blind spot region, and outputting audible, tactile or visual feedback, via an output system, to a rider of the motorcycle when the motorcycle is determined to be located in the blind spot region.