Wilson taught at Bryn Mawr College in Pennsylvania; Wesleyan University in Middleton, Connecticut; and then at his alma mater, Princeton, beginning in 1890. While at Princeton, he taught short courses at John Hopkins and New York Law School. His prominence as a leader in academics grew. The Universities of Illinois and Virginia offered him the position of university president. Princeton—wanting to keep him—also offered him the position of president in 1902. He accepted and remained president of Princeton until 1910.