After getting his law degree, Alfred moved to Wheaton, Illinois, where he joined his brother, John, who operated a law partnership. Alfred married Jane Barnes around 1940, then joined the United States Navy with the rank of Ensign and served in the Pacific Theater, as a communications officer. He married Jane Upshur and had two sons and a daughter, Robert Upshur Woodward, in 1943, David Woodward, and Anne Woodward. Alfred was promoted to the rank of Lieutenant in 1945. He was discharged from the Navy in January 1946 and he went home to Wheaton and joined his brother's law firm. Later after a divorce, Alfred would marry Alice Elizabeth Ensko (1924–1999) who had three children of her own, Lynn, Michael, and Susan, and they had one daughter together, Wendy Woodward.