An imaging system and method generate image data within a field of view that includes a cab of the vehicle and a portion of a route being traveled on and/or wayside devices disposed along the route. The cab includes a space where an operator of the vehicle is located. The image data generated by the camera is examined to identify route damage, a deteriorating condition of the route, and/or a condition of the wayside devices. The condition of the wayside devices can include damage to the wayside devices, a missing wayside device, deterioration of the wayside devices, or a change in terrain.