Santa Fe Trail is a 1940 American western film directed by Michael Curtiz and starring Errol Flynn, Olivia de Havilland, Raymond Massey, Ronald Reagan and Alan Hale. Written by Robert Buckner, the film is about the abolitionist John Brown and his campaign against slavery prior to the American Civil War. In a subplot, J. E. B. Stuart and George Armstrong Custer compete for the hand of Kit Carson Holliday.

The film was one of the top-grossing films of the year, and the seventh Flynn–de Havilland collaboration. Its content has little relevance to the actual Santa Fe Trail.

Plot
At West Point Military Academy in 1854, cadet Carl Rader (Van Heflin), an agent of John Brown, is dishonorably discharged for distributing anti-slavery pamphlets. His classmates Jeb Stuart (Errol Flynn) and George Custer (Ronald Reagan) become second lieutenants and are posted to Fort Leavenworth, Kansas Territory, the most dangerous duty in the army—an assignment they relish. On the way to Kansas, Custer and Stuart meet Cyrus K. Holliday, in charge of building the railroad to Santa Fe, New Mexico, and his daughter Kit (Olivia de Havilland), with whom both officers fall in love.

The Kansas Territory is bloodstained and war-torn, a victim of John Brown’s (Raymond Massey) relentless crusade against slavery. Meanwhile, Rader has enlisted as a mercenary in Brown’s army, which has been terrorizing the countryside. During Brown’s attack on a freight wagon under the protection of the U.S. Army, Stuart and Custer capture Brown’s injured son Jason (Gene Reynolds) and, before he dies, the troubled boy informs them about his father’s hideout at Shubel Morgan’s ranch in Palmyra. In disguise, Stuart rides into Palmyra, the center of the Underground Railroad, but Brown’s men spot his horse’s army brand. He is captured and taken to Brown at gunpoint. Attempting to escape, Stuart is trapped in a burning barn but is saved as Custer leads the cavalry to the rescue, driving Brown into seclusion.

Three years later, in 1859, believing that Brown’s force has been broken, Stuart and Custer are sent back to Washington, D.C., where Stuart proposes to Kit. However, Brown is planning to re-ignite war by raiding the arsenal at Harper’s Ferry, Virginia. When Brown refuses to pay Rader for his services, Rader rides to Washington to alert Stuart of Brown’s plans, and the troops arrive just in time to crush the rebellion. Brown is then tried for treason by the state of Virginia and hanged. The movie ends with the marriage of Stuart and Kit.

Cast
Olivia de Havilland and Errol Flynn in Santa Fe Trail
Errol Flynn as James “Jeb” Stuart
Olivia de Havilland as Kit Carson Holliday
Raymond Massey as John Brown
Ronald Reagan as George Armstrong Custer
Alan Hale as Tex Bell
William Lundigan as Bob Holliday
Van Heflin as Carl Rader
Gene Reynolds as Jason Brown
Henry O’Neill as Cyrus K. Holliday
Guinn Williams as Windy Brody
Alan Baxter as Oliver Brown
Moroni Olsen as Robert E. Lee
Ward Bond as Townley
Erville Alderson as Jefferson Davis
David Bruce as Phil Sheridan
Spencer Charters as Conductor
Creighton Hale as Telegraph Operator (uncredited)
Jack Mower as Surveyor (uncredited)