Westover attended the Air Service Balloon School in 1921, and the Air Service Airship School in 1922. He continued on to heavier-than-air flight training, completing the Air Service Primary Flying School at Brooks Field and the Advanced Flying School at Kelly Field in 1923 at the age of forty. As a result of these courses, Westover was awarded aeronautical ratings as a balloon observer, airship pilot, airplane pilot, and airplane observer, at that time every rating authorized by the Air Service.