A trailer sideswipe avoidance system for a vehicle towing a trailer is provided herein. The trailer sideswipe avoidance system includes a sensor system configured to detect objects in an operating environment of the vehicle. A controller receiving inputs from the sensor system is configured to determine a travel path of the towed trailer as the vehicle turns, determine whether an object detected in the operating environment of the vehicle is in the travel path of the towed trailer, determine a time until sideswiping of the object with the towed trailer, compare the time until sideswiping with a threshold time value, and prompt one or more vehicle systems to execute a sideswipe avoidance measure when the time until sideswiping is less than the threshold time value.