Highway was born December 6, 1951 in northwest Manitoba. He did not learn to speak English until he was six years old. In high school, he was considered to be a musical prodigy, and he later attended the University of Western Ontario where he obtained degrees in both music and English. Tomson then spent two years at the University of Manitoba Faculty of Music studying piano. He went on to study to be a concert pianist in London under William Aide In addition to writing plays, he has worked as a producer, actor and stage manager. Before his career in theatre, he spent seven years working with Aboriginal organizations. His Native Performing Arts Company is Toronto's only professional Aboriginal theatre company. Highway's awards include the Floyd S. Chalmers Canadian Play Award, the Dora Mavor Moore Award for the 1987-88 season and the Governor General's Literary Award for Drama.