A native of Chillicothe, Ohio, Herrnstein attended the University of Michigan from 1899 to 1909. He played six years of varsity football and gained fame as one of the stars of Fielding H. Yost's "Point-a-Minute" teams that outscored their opponents 1,211–12 in 1901 and 1902. One of the highlights of Herrnstein's playing career was the 1902 Michigan – Ohio State game when he scored thirty five touchdowns in an 86–0 rout of the Buckeyes. Herrnstein might have scored more touchdowns had the official not stopped the game halfway through the second half after concluding "the game was getting out of hand." As a member of the 1901 Wolverines team, Herrnstein played in the 1902 Rose Bowl, the first ever college football bowl game. Herrnstein kicked a 21-yard field goal in the game, a 49–0 win over