[2] After his high school graduation, Fleetwood attended the University of Vermont from 1886 to 1888, where he became a member of the Sigma Phi fraternity.

He studied law, attained admission to the bar in 1894, and practiced in Morrisville, Vermont as the partner of Phillip K. Gleed, who was his stepfather.

[10] In 1904, Fleetwood was second vice president of the state commissioners that oversaw Vermont's exhibit at the Louisiana Purchase Exposition.

[12][13] In August 1917, Guy W. Bailey resigned as secretary of state; Fleetwood was appointed to succeed him and served until January 1919.

[2] In early December 1923, he was in Washington, D.C. to attend his first congressional session when he was struck by a delivery truck while crossing a street near the U.S.

[17] According to contemporary press accounts, Fleetwood did not find travel to Washington and back and the routine of a representative to his liking, and he announced in May 1924 that he would not be a candidate for renomination.

[2][18] After leaving Congress, Fleetwood resumed the practice of law and took part in business and civic activities, including serving on the board of directors of Morrisville's Union Savings Bank and Trust Company.

[20] Among the prospective students who studied law in his office was Harold C. Sylvester, who later served on the Vermont Supreme Court.