From 1919 to 1923, he attended Texas A&M University, graduating with a bachelor of science degree in mechanical engineering, and getting his commission in the United States Army Air Service.

He was promoted to major in March 1940 and to lieutenant colonel in December 1941, the latter coming while he was in the Panama Canal Zone as commanding officer of the 16th Pursuit Group and chief of staff of the 6th Air Force.

Under him this combat unit gained fame for its close air support of General George Patton's U.S. Third Army in the successful movement across France in August 1944 and Germany in the spring of 1945.

Weyland's widely recognized ability and experience in tactical warfare was demonstrated in ten major campaigns in Korea.

[2] During his career, he earned many decorations, including two Distinguished Service Medals, the Silver Star, the Distinguished Flying Cross (for personally leading a bomber formation against important Communist targets in North Korea when weather prevented fighter cover and escort), the Legion of Merit, Bronze Star, and Air Medal, as well as awards from Great Britain (Commander, Order of the British Empire—for air cover of the Normandy Invasion), France, Luxembourg, Belgium, Korea, Thailand, the Philippines, Japan and Brazil.