Littlefield was born in Lebanon, Maine on June 21, 1851. He attended the common schools and Foxcroft Academy. He studied law, was admitted to the bar and practiced in Rockland. Littlefield served as a fellow at Bates College from 1899 to 1915.[1]
He was elected a member of the Maine House of Representatives 1885–1887 and served as speaker the last year. He was elected Attorney General 1889–1893. He was a delegate to the Republican National Conventions in 1892 and 1896. He was elected as a Republican to the Fifty-sixth Congress to fill the vacancy caused by the death of Nelson Dingley, Jr. Littlefield was reelected to the four succeeding Congresses and served from June 19, 1899, until his resignation, effective September 30, 1908.[2] He was Chairman of the Committee on Expenditures in the Department of Agriculture (Fifty-ninth and Sixtieth Congresses).
He moved to New York City and engaged in the practice of law until his death there on May 2, 1915. His interment is in Achorn Cemetery in Rockland.
^General Catalogue of Bates College and Cobb Divinity School, 1863-1915 by Bates College Lewiston, Me, Me Lewiston, Cobb Divinity School Lewiston, Me, Cobb Divinity School, Bates College (Lewiston, Me.) Cobb divinity school, Me.) Bates College (Lewiston, Published by The College, 1915)[1]