He worked as a journalist and translator in the United States, before returning to Canada where he served as Bertie Township's assessor, then its treasurer, then became Reeve of Fort Erie and Warden of Welland County.

Rising to the rank of brigadier-general in 1915, he commanded Military District 13, which was headquartered in Calgary, Alberta.

[2] [4][5][6] At the end of the First World War, Cruikshank was assigned to Ottawa where he was appointed director of the Historical Section of the General Staff.

Among his most notable writings were: The Story of Butler's Rangers and the Settlement of Niagara (1893), A memoir of Colonel the Honourable James Kerby (1931), The Settlement of the United Empire Loyalists on the Upper St. Lawrence and Bay of Quinte in 1784 (1934), The Life of Sir Henry Morgan (1935), The Political Adventures of John Henry: The Record of an International Imbroglio (1936) and the edited volumes of the papers of John Graves Simcoe.

[4][5] The plaque in Ottawa is located on the grounds of the former Canadian War Museum building and reads: "A noted authority on the history of Ontario, Cruikshank became the first director of the Historical Section of the Adjutant-General's Branch of the General Staff in 1918.