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Train robbery was a type of robbery, in which the goal was to steal money or other valuables being carried aboard trains. Trains carrying payroll shipments were a major target. These shipments would be guarded by an expressman whose duty it was to protect the cargo of the "express car". Expressmen, conductors, and other personnel took enormous pride in their duty and had no problem with risking their lives for a shipment. Bandits would rely on the expressman to open the safe and provide the goods. Without the combination required for the combination lock, it was almost impossible to break into the safes. However, the invention of dynamite made it much easier to break into safes and rob the train.

If the outlaw was unsatisfied with the goods, passengers of the train's carriages who generally would be unarmed would be held at gunpoint and made to hand over any valuables they were carrying, usually in the form of jewelry or currency.

Contrary to the method romanticized by Hollywood, outlaws generally never jumped from horseback onto a moving train. Usually, they would either board the train and wait for a good time to initiate the heist, or they would stop or derail the train and then begin the holdup.

Famous train robbers include Bill Miner, Jesse James and Butch Cassidy. James is mistakenly thought to have completed the first successful train robbery in the American West when on July 21, 1873 the James-Younger Gang took US $3,000 from the Rock Island Railroad after derailing it southwest of the town of Adair, IA. The derailment killed the engineer. However, the first peacetime train robbery actually occurred on October 6, 1866, when robbers boarded the Ohio & Mississippi train shortly after it left Seymour, Indiana. They broke into one safe and tipped the other off the train before themselves jumping off. The Pinkerton National Detective Agency later traced the crime to the Reno Brothers. There was one earlier train robbery in May of 1865, but because it was committed by armed guerrillas and occurred shortly after the end of the Civil War, it is not considered to be the first peacetime train robbery in the United States.

• Frank, Jesse, Sim, and Jack Reno (The Reno Brothers)
• Cole, Jim, John, and Bob Younger (Younger Brothers)
• The Dalton Gang
• The Evans Gang
• Bill Miner
• Black Jack (Tom) Ketchum
• Jesse James and the James Gang
• Butch Cassidy and the Sundance Kid
• The Wild Bunch
• Bill Doolin
• Little Dick West
• George Newton
• Tulsa Black Jack
• Sam Bass
• Charlie Ballard
• Peg-Leg Eldridge
• Big Nose George Parrot
• Quail Hunter Jack Kennedy

• Great Gold Robbery of 1855, London - Paris (1855)
• Bezdany raid, Lithuania (1908)
• Kakori train robbery, India (1925)
• Great Train Robbery, England (1963)

• The Great Train Robbery, film (1903)
• The Great Train Robbery, novel (1975)

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