He studied literature and rhetoric at Syracuse University, earning a Bachelor of Arts degree in 1894.
He served as the founding chairman of the History Department of Rhode Island State College, and was the namesake of the Herman Churchill Award for Excellence in History given annually to the top honors history student at the University of Rhode Island. He earned his Master of Arts in Letters from the University of Wisconsin–Madison in 1902. Churchill married Cora Mae Boyce on 15 June 1898 in Menomonie, Wisconsin, and they had three children: Irving Lester Churchill (1901-1995), Florence Hermenia Churchill (1905-1920), and Arthur Chester Churchill (1911-2001).
Churchill began his academic career as an instructor of English literature at Northwestern University in Evanston, Illinois in 1903.
In the fall of 1907, he accepted a position as head of the English Department at Southwestern College in Winfield, Kansas until 1909 when he accepted a similar position at Nebraska Wesleyan University in Lincoln, Nebraska. In 1912, Churchill made his final move in accepting the position as head of the Department of Rhetoric and Composition at Rhode Island State College.
Afterward in 1921, Churchill was appointed as the founding head of the History Department by the college president, Howard Edwards. During his professional career, Churchill was active in civic affairs in the community, serving as president of the Tavern Hall Club in 1929, and he was active in genealogical research.
He was active in the Phi Beta Kappa academic honor society and Beta Theta Pi fraternity and was a charter signatory of the Rhode Island chapter of the Phi Kappa Phi honor society.
He died at his home in Kingston, Rhode Island on 13 April 1941, shortly after retiring from the college in 1940.