Born near Rockwood, Upper Canada, Hill moved to Minnesota in 1856 settling at St. Paul. Having organized the Red River Transportation Company which provided effective transportation between St. Paul and Winnipeg, he had begun, by 1878, to build his vast railway empire. A member of the Board of the CPR (1880-3) he subsequently became its greatest competitor and by 1889 had organized the Great Northern System. As President of that System (1893-9) and Chairman of the Board (1907-12) he built numerous feeder lines reaching to the Canadian border.