Wedemeyer attended St. Louis School in Honolulu and was a standout in both football and baseball. Wedemeyer, a halfback, played college football for the St. Mary's College Galloping Gaels in Moraga, CA. In 1945, he finished fourth in the Heisman Trophy voting, and he was inducted into the College Football Hall of Fame in 1979. Wedemeyer was Hawai'i's first consensus All-American football player. He bore the colorful nicknames 'Squirmin' Herman,' 'The Flyin' Hawaiian,' 'The Hawaiian Centipede,' and 'The Hula-Hipped Hawaiian.'