At one time, the stagecoach was a tempting target for outlaws. They could stop a coach far from the prying eyes of the law, stealing the cargo and robbing the passengers. As trains began moving across the country, they replaced the stagecoach for long-distance transportation. They also became the new target for outlaws. Train robbery was common in the United States and is associated with outlaw gangs in the American West.
On this date in 1866, what is generally recognized as the first train robbery occurred when the Reno brothers boarded a passenger train near Seymour, Indiana. Wearing masks and waving guns, they entered the Adams Express car and emptied the safe.
This incident seemed to inspire other similar robberies. Sometimes, the robbers derailed trains, causing injuries to passengers and crew. In 1868, another Adams Express car was robbed, and this time, the criminals got away with $40,000. That would be worth almost one million dollars today.
The vast wilderness of Dakota Territory became a target for train robbers. In the spring of 1886, two cowboys robbed a Northern Pacific train at Richardton. They got away with the impressive sum of $60,000. Although Sheriff Jerry Hayes of Dickinson quickly formed a posse and took up the chase, the robbers got away. One of them was finally arrested two years later and spent fifteen years in the Bismarck Penitentiary for his crime.
The following year, outlaws calling themselves the Black Hills Gang stopped a Union Pacific train as it headed to Custer City. They robbed the passengers, and in the security car, they found a box containing $60,000 in gold coins. The leader of the gang was the notorious Texas outlaw Sam Bass.
The gang split up after the robbery, but there is one more North Dakota connection to the story. Outlaw William Collins was arrested in Texas. After jumping bail, he wound up in Pembina, where he took a job as a bartender. When a U.S. Marshal arrived in town looking for Collins, there was a shootout straight out of a movie that resulted in the deaths of both men.
Train robberies were common until the 1890s. At that point, they became less frequent, but they still occur today. In 2025, a gang broke into a train and stole a shipment of Nike shoes.
Dakota Datebook written by Dr. Carole Butcher
Sources:
- Dickinson Museum Center. “Richardton Robbery – 1886.” https://dmc.omeka.net/items/show/457Accessed 9/8/2026.
- Legends of America. “Train Robberies of America.” https://www.legendsofamerica.com/train-robberies/Accessed 9/8/2026.
- South Dakota Public Broadcasting. “The Big Springs Train Robbery of 1887.” https://www.sdpb.org/rural-life-and-history/The-Big-Springs-Train-Robbery-of-1887Accessed 9/8/2026.
- History. “The Reno Brothers Carry Out the First Train Robbery in US History.” https://www.history.com/this-day-in-history/october-6/first-u-s-train-robberyAccessed 9/8/2026.
- Round Rock, Texas. “The Story of Sam Bass.” https://www.roundrocktexas.gov/city-departments/planning-and-development-services/historic-preservation-2/the-historic-round-rock-collection/sam-bass/Accessed 9/8/2026.
- Native Legends. “The Pembina Shootout.” https://www.nativelegends.info/the-pembina-shootout-of-1878-a-tragic-frontier-confrontation/Accessed 9/8/2026.
