Middleton was involved in numerous activities during his college days, and took leadership roles in most of them. He was the vice president of A&M's Collegian Club, and president of the school's Gun Club, being photographed on one occasion with his beloved shot gun, which he was allowed to keep in his dormitory room and use for hunting on weekends when campus activities did not fill his schedule. He was the president of his junior class and during his senior year was the commandant of the select Mississippi Sabre Company, which was a club restricted to seniors of good social, academic and military standing. Among his favorite activities were baseball and football, and he played both sports throughout college. Early in his tenure, however, he had to give up a season of baseball when he failed a chemistry course, and spent his afternoons back in the classroom and laboratory instead of on the athletic fields. Whether playing or spectating, the baseball and football games gave the students a chance to leave campus, and they took the train to play various teams around the state or region. Games were played wherever a suitable field could be found, but football games against the University of Mississippi were always played in Jackson.