Born in Newburgh of United Empire Loyalist ancestry, Aylesworth was educated at the University of Toronto, and called to the Ontario Bar in 1878. As the Canadian member of the Alaska Boundary Tribunal in 1903, he presented his country's views in a minority report. Elected to the Dominion parliament in 1905, he served in the cabinet of Sir Wilfred Laurier as postmaster-general and minister of labour, 1905-06, and minister of justice, 1906-11. He acted as British representative at the North Atlantic Fisheries Arbitration in The Hague, 1910-11, and was knighted for his services. In 1923 he was appointed to the Canadian Senate.