Santa Fe Trail is a 1940 American Western film directed by Michael Curtiz and starring Errol Flynn as J. E. B. “Jeb” Stuart, Olivia de Havilland, Raymond Massey as John Brown, Ronald Reagan as George Armstrong Custer and Alan Hale. Written by Robert Buckner, the film is critical of the abolitionist John Brown and his controversial campaign against slavery before the American Civil War. In a subplot, Jeb Stuart and George Armstrong Custer—who are depicted as friends from the same West Point graduating class—compete for the hand of Kit Carson Holliday.

In 1854, Jeb Stuart, George Custer and other graduates from West Point are posted to Kansas to help pacify the territory before railroad construction to Santa Fe can resume.