Henry Stewart Caulfield (December 9, 1873 – May 11, 1966) was an American lawyer and Republican politician from St. Louis, Missouri.

From 1910 to 1912 Caulfield served as Judge of the Missouri Court of Appeals for the Eastern District, based in St. Louis.

In 1914 Caulfield served as counsel for the St. Louis City and County Board of Freeholders.

Caulfield vetoed the bill, which forced Missouri's U.S. House members to run at-large, resulting in Democratic candidates winning every seat.

He was the unsuccessful Republican nominee for United States Senator in 1938, losing to incumbent Democrat Bennett Champ Clark.