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The Dierks High School win in the Friday Night 5G Lights competition has everyone talking about Arkansas, and all this outlaw talk made me think about Arkansas history. We are a storied place full of hideouts and legendary characters. So, I decided to do some digging. Yes, some of the most notorious crime bosses, gangsters, and their runners used the hills of the Ozarks and Spa City to “blend in,” but we created our own set of rebellious troublemakers!
In the days when dirt roads crossed wild rivers, and justice was carried on horseback, Arkansas was more than a frontier—it was a refuge for renegades. From notorious bandits hiding in Ozark caves to moonshiners who turned backwoods enterprise into legend, the state’s history is filled with colorful characters who defied the law and shaped local lore.
These six outlaws symbolize the grit and rebellion that helped shape Arkansas’s wild spirit. And the best part? You can still visit the towns, trails and museums that carry their stories.
Cherokee Bill | The Terror of Fort Gibson
Crawford Goldsby, known as Cherokee Bill, was as charming as he was dangerous. A mixed-heritage outlaw active in the 1890s, he robbed stores, trains, and post offices across Indian Territory before being captured and tried in Fort Smith. His trial and hanging became a spectacle under Judge Isaac Parker’s court, cementing his place in frontier history.
Arkansas tells his story at the Fort Smith National Historic Site, where visitors can walk through the courtroom and jail where Cherokee Bill’s last days took place. The nearby U.S. Marshals Museum offers a modern perspective on the Wild West’s complex legacy of law and order. The Saunders Museum in Berryville displays one of his famous shooting pistols stored in a private collection.
Conway “Boss” Johnson | The Ozark Moonshine King
Conway “Boss” Johnson wasn’t a gunslinger or train robber; he was a master of evasion and enterprise. Operating deep in the Ozark Mountains during Prohibition, he built hidden stills and supplied bootleg whiskey across Newton and Searcy counties. Locals admired his resourcefulness, and tales of how he outsmarted federal agents became local legend.
Arkansas shares its story: Head to the Ozark Folk Center State Park in Mountain View, where interpreters tell tales of Ozark ingenuity and backwoods survival. The Newton County Heritage Museum in Jasper also showcases local Prohibition history and the colorful characters who shaped the region’s independence. The Crystal Ridge Distillery in Hot Springs tells the story of moonshine in Arkansas and offers tastes of their house blend along the way!
Jesse James | The Robin Hood of the Ozarks
No outlaw captures the American imagination quite like Jesse James. As the leader of the James-Younger Gang, he carried out daring train and bank robberies across the Midwest. When the law closed in, he often slipped into the Ozark Mountains, finding refuge among Arkansas’s caves and sympathizers.
Arkansas hid his story: Follow local legends along the Buffalo National River near Ponca and Jasper, where “Jesse James Cave” remains part of local folklore. The Thunder Canyon Falls trail near Jasper offers a loop that 36 Ozark fugitives once sought. Don’t miss the chance to swing through Mena, where the 1821 log cabin in Janssen Park held James on more than one occasion as he navigated the mountains. And if you need more routes, the Twisted Lady motorcycle path is said to take you near the home of Frank James, father of the dueling gangs that often housed these outlaws.
The Rufus Buck Gang | Rebellion on the Border
The Rufus Buck Gang’s story is short, violent and unforgettable. This group of young men, of African and Native descent, led a brief rebellion against U.S. authorities in 1895, committing robberies and assaults they saw as revenge for injustices in Indian Territory. Their rampage ended in Fort Smith, where they were tried and executed together.
Arkansas holds their story: The Fort Smith National Historic Site highlights its history within the broader context of Judge Parker’s court and the complex racial tensions of that era. Downtown Fort Smith’s walking tours and murals illustrate how the city’s history is closely linked to both the lawmen and the lawbreakers who shaped it.
Bill Doolin | The Last of the Wild Bunch
Bill Doolin was one of the last major outlaws of the American frontier. Born near Clarksville around 1858, he worked as a ranch hand and cowboy before turning to a life of crime. After briefly riding with the Dalton Gang, Doolin formed his own infamous crew known as the “Wild Bunch.” His gang robbed banks, trains, and stagecoaches across the Midwest and Great Plains, often retreating into the rugged Ozarks when the law got too close. The famed “Three Guardsmen” tracked him down in Oklahoma before he met his end.
Explore his story: Travelers can delve into Doolin’s roots at the Johnson County Historical Society in Clarksville, which preserves the grit and legend of their native sons. The Fort Smith National Historic Site highlights the lawmen of the era who pursued Doolin and his gang across the border. For an authentic taste of his wild country, the Ozark National Forest offers scenic drives and hiking trails through the same rugged landscapes that once concealed Arkansas’s most elusive outlaw.
“Machine Gun” Kelly | The Gangster Who Hid in Fort Smith
By the 1930s, Arkansas’s outlaw stories had shifted from horses to getaway cars. George “Machine Gun” Kelly was one of the most infamous gangsters of the era, known for kidnapping oil tycoon Charles Urschel. His wife, Kathryn, a native of Arkansas, and the couple briefly hid in Fort Smith, blending into city life as the FBI moved in.
Arkansas Stops: Explore the Prohibition era at the Fort Smith Museum of History, which features exhibits from the 1930s gangster period. Stroll through historic downtown Fort Smith, where preserved architecture from Kelly’s era offers a look into the city’s lively riverfront history. And don’t miss Hot Springs, once controlled by the infamous Al Capone and his mobsters. The Gangster Museum of America showcases the stories and artifacts of these gangsters.
Other stories you may love:
- Outlaws in Arkansas
- Hideouts and Caves in Arkansas
- Dierks High School Outlaws Football Stadium Win
- The Hanging Judge
- Bass Reeves: The Legend
- Sidney Thompson: Reclaiming the Bass Reeves Legend
- Exploring the Fort Smith National Historic Site
- S. Marshal’s Museum
From the gallows of Fort Smith to the caves of the Buffalo River, Arkansas’s outlaw past is more than a collection of old stories; it’s woven into the landscape. These hills and hollows still echo with tales of risk, rebellion and redemption.
Images throughout the story are used under the public domain rule.
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