Oklahoma has a long and rowdy history, filled with pioneers, outlaws, oil barons, and everyday folks just trying to get by. But every so often, someone decided they didn’t want to “get by” the regular way—they wanted to take by force. And that’s where our story today begins.
On March 13, 1894, the Doolin-Dalton Gang—one of the most notorious outlaw groups in the Wild West—struck the railroad station in Woodward, Oklahoma, in a brazen robbery that added yet another chapter to their long and bloodstained legacy.
This wasn’t just some run-of-the-mill stickup. This was a well-planned, high-stakes heist by two of the most wanted men in America: Bill Doolin and Bill Dalton. These two were the masterminds behind a gang that made a living robbing banks, trains, and the occasional unlucky lawman who got in their way.
But before we get into what went down on this fateful night, let’s set the stage.
Woodward, Oklahoma: A Lawless Frontier Town
In the late 1800s, Woodward was one of those places that walked a fine line between civilization and the Wild West. Located in the heart of Oklahoma’s cattle country, it was a boomtown built on ranching and the railroad.
The Atchison, Topeka & Santa Fe Railway ran right through town, making it a prime target for outlaw gangs looking for a big payday. The town itself had its share of lawmen, but out here, the bad guys had just as much power as the sheriffs—sometimes more.
The railroad station was a hub of activity: train passengers coming and going, shipments of goods arriving, and—most importantly—money flowing in and out. And where there was money, there were outlaws.
Enter the Doolin-Dalton Gang.
The Daring Heist: March 13, 1894
On the night of March 13, the outlaws rode into town under the cover of darkness. Bill Doolin and Bill Dalton had a simple plan: bust into the railroad station, force the station agent to hand over the money, and get the hell out of town before the law even knew what hit them.
It started smoothly. The gang stormed into the station, guns drawn, and quickly overpowered the station agent. They demanded the cash, knowing full well that railroad stations handled large sums of money from ticket sales, shipments, and payroll deliveries.
The agent—probably sweating bullets—had no choice but to hand over the cash.
But here’s where things get interesting. Unlike Hollywood-style train robberies, this job wasn’t exactly a massive windfall. The exact amount they got away with is lost to history, but let’s just say it wasn’t the kind of jackpot they were hoping for. It was enough to keep the gang fed and on the run, but not enough to retire on.
However, what they did get was something far more valuable: reputation.
The Doolin-Dalton Gang’s growing list of crimes was making them folk legends—outlaws who defied authority and lived outside the law. Their name struck fear into townspeople and frustration into lawmen.
And speaking of lawmen…
The Getaway and the Manhunt
After securing the cash, Doolin and Dalton hightailed it out of Woodward before anyone could get a posse together. By the time the local sheriff and his deputies figured out what had happened, the gang was already long gone, leaving only dust and empty pockets behind.
This robbery added another bounty to their already sky-high wanted posters. The Doolin-Dalton Gang had been making a name for themselves robbing trains and banks all across Oklahoma and Kansas.
Bill Doolin, in particular, was considered one of the most dangerous outlaws of his time. Unlike some outlaws who killed for sport, Doolin was more of a businessman—he just happened to do his “business” at gunpoint. His right-hand man, Bill Dalton, came from a long line of criminals. His brothers were part of the original Dalton Gang, a group that met a bloody end in a failed bank robbery in Coffeyville, Kansas, in 1892.
Bill Dalton must have learned a thing or two from his brothers’ mistakes because he and Doolin managed to stay one step ahead of the law for a while longer.
But in the end, time caught up with them.
The Fate of the Outlaws
The Doolin-Dalton Gang didn’t last forever. The law finally caught up with Bill Dalton in 1894—just months after the Woodward robbery. He was tracked down and gunned down by a posse in Ardmore, Oklahoma.
Bill Doolin lasted a little longer, but not by much. He was captured in 1896 and briefly imprisoned before making a daring escape. But that freedom didn’t last. Later that year, a posse led by legendary U.S. Marshal Heck Thomas found him hiding in Lawson, Oklahoma, and shot him dead.
With their leaders gone, the Doolin-Dalton Gang fell apart. One by one, the remaining members were captured or killed. The Wild West was changing, and lawmen were getting better at tracking down the bad guys.
The Legacy of the Woodward Robbery
So, was this one of the biggest robberies in Oklahoma history? Not exactly. The gang didn’t make off with a fortune, and no legendary shootout followed.
But it was another piece of the puzzle—a moment in time that showcased Oklahoma’s wild past and the men who tried (and usually failed) to outrun the law.
Today, Woodward is a quiet town with a population of around 12,000. But if you walk the streets at night, you might wonder: is there still a little outlaw spirit left in the air?
One thing’s for sure—on March 13, 1894, the Doolin-Dalton Gang reminded everyone in town that in the Wild West, nobody was ever really safe.
Final Thoughts
Oklahoma’s history is full of stories like this—outlaws, lawmen, and ordinary folks caught in extraordinary times. Every day, something happened that shaped this state into what it is today.
And that’s why we’re here—to bring these stories back to life, one day at a time.
So, stay tuned for tomorrow’s Today in Oklahoma History feature. Who knows what we’ll dig up next?
Sources & Further Reading:
- Outlaw Tales of Oklahoma by Col. Charles W. Sasser
- The Encyclopedia of Oklahoma History and Culture (OHS)
- National Cowboy & Western Heritage Museum archives
