History

Chadron to Chicago

In 1893 a joke planted in eastern newspapers turned into a thousand-mile horse race from a Pine Ridge railroad town to Buffalo Bill's arena at the Chicago World's Fair, and its result is still argued.

The Chadron to Chicago cowboy race of June 1893: the hoax that started it, the humane societies' inspectors, Doc Middleton and John Berry, the finish at Buffalo Bill's Wild West, and the three versions of who won.

By Open Road Guide·October 23, 2026·3 min read

In the spring of 1893 newspapers back east reported that hundreds of wild cowboys would race their horses from Chadron to the World's Columbian Exposition in Chicago. Nobody in Chadron had planned any such thing. The story began as a joke. One telling credits Emmett Albright, a Texas cowboy living in Crawford; another credits John G. Maher, the Dawes County clerk, a practical joker who wrote for eastern papers. The Sidney Sun-Telegraph's account has Albright starting the rumor and Maher dressing it up and sending it out. Either way it got loose, people took it seriously, and Chadron decided it had better hold a race.

The rules

The committee wrote rules. Riders had to use western-bred horses, two apiece, ridden and led in turn, under a stock saddle of at least 35 pounds, with rider and saddle together weighing no less than 150. The purse was $1,000, and Buffalo Bill Cody, whose Wild West was playing in Chicago that summer, added $500 and asked that the race finish at his show.

Humane societies remembered the military ride from Berlin to Vienna the year before, when more than 30 of some 230 horses died or were destroyed, and they tried to stop the race. They settled for inspectors who followed the riders and examined the horses at checkpoints, and the riders agreed to withdraw any horse that looked mistreated or unfit to go on.

The ride

Nine riders left the Blaine Hotel in the early evening of June 13, 1893. The local favorite was Doc Middleton, who had once led a gang of horse thieves called the Pony Boys and now lived in Chadron. The others included Joe Gillespie, Rattlesnake Jim Stephens, Charley Smith and John Berry, a former stagecoach driver who had helped lay out the route, which the other riders held against him. The road ran east through Rushville and across the Sandhills to Long Pine and O'Neill, crossed into Iowa at Sioux City, and went on by Fort Dodge, Dubuque and Freeport.

Berry rode carefully and saved his horses. He reached Cody's grounds about 9:30 on the morning of June 27, thirteen days and sixteen hours out, having covered about 1,040 miles. Cody called him "the sorriest, sleepiest, tiredest man anyone has ever seen." Gillespie came in behind him. Albright finished too and was disqualified when it came out that he and his horse had ridden much of the way on a stock train. Seven of the nine reached Chicago.

Who won

Who won is still argued. One account has the committee awarding Berry the prize. The state historical marker in Chadron says he was disqualified for knowing the route in advance and that Chadron's officials declared Gillespie the winner. Another says the purse was shared among the riders, with a Montgomery Ward saddle for Berry and a gold-plated Colt revolver for Gillespie. That revolver survives, documented by the Dawes County Historical Society as Gillespie's prize for winning.

The marker stands on Second Street in downtown Chadron, where the riders set out. US-20 still leaves town the way they went, east past the Museum of the Fur Trade toward Rushville.

Places in this story

Museum of the Fur Trade
Chadron

A museum of what traders and Native nations exchanged, from the oldest known point blanket to a Lakota leader's silver cross, beside the rebuilt Bordeaux trading post east of Chadron.

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