The Insane 6-Day, 500-Mile Race That Riveted America

by Matthew Algeo

This story originally appeared in the March/April 2015 issue of mental_floss magazine.

It was just after midnight on Monday, November 15, 1875, and the Interstate Exposition Building in Chicago was buzzing. Spectators swarmed the auditorium, hundreds of people craning their necks to get a glimpse of the two legends on the track. One of the men wore a black velvet suit with black boots, a silk sash draped across his chest. The other looked the part of a conventional athlete in white tights and a striped tank top. They stretched their legs, then approached the line. As the crowd roared, the starter counted: “One! Two!”

On “Three!” they were off. With hips swiveling and arms pumping, the Great Walking Match for the Championship of the World had begun.

In the 1870s and 1880s, competitive walking—formally known as pedestrianism—was America’s most popular spectator sport. As cities grew and the nation industrialized, people found themselves with spare time and a little money to burn. The country’s mood had also changed post–Civil War: A stern antebellum work ethic had given way to a new appetite for simple fun. And competitive walking was certainly simple. Matches cost little to stage, and competing required no special equipment. Before long, the nation was swept up in “walking fever.”

The men on the track were Edward Payson Weston and Dan O’Leary, and what played out before a screaming fan base was more than just a race. Weston, a New England dandy who often competed in flashy outfits, was the man to beat. He’d made his name eight years earlier, when he walked the 1,200 miles from Portland, Maine, to Chicago in under 30 days, winning a $10,000 wager in the process. A blue-blooded Yankee, Weston embodied old money and an old America.

O’Leary’s story couldn’t have been more different. Born in County Cork, Ireland, he had arrived in the States, alone and penniless, some 10 years earlier. Finding opportunity in a burgeoning sport, O’Leary had jumped into pedestrianism less than two years prior to this race, walking an astounding 116 miles in under 24 hours and establishing himself as the working man’s hero. He also became Weston’s biggest rival. This was the first time the two squared off, and the public was lapping up the hype.

For Chicago’s Irish community, O’Leary wasn’t just an athlete; he was a symbol of hope. Four years earlier, another O’Leary—Catherine (no relation)—had been blamed for igniting the Great Fire of 1871 when her cow supposedly knocked over a lantern. In a city devastated by the flames, Catherine became a convenient scapegoat, an easy punching bag for an angry and xenophobic populace. Tension between the city’s Irish immigrants and its “native” population had only grown worse. And in that divide, Dan O’Leary was left carrying his community’s dream on his back—hoping to prove an Irishman’s worth by walking his way to glory.

The rules for the walk-off were clear: The first man to walk 500 miles would be declared the winner. Running was not permitted. Each competitor was required to keep one foot in contact with the ground at all times while on the track. Also, the race would take place on two concentric tracks made of pressed mulch, more commonly known as “the tanbark.” To a generation of Americans, the tanbark was the gridiron of its day.

The men had to adhere to one more rule: Under no circumstances could the race continue beyond midnight the following Saturday. At the time, Chicago, like nearly every other city in the United States, had blue laws that prohibited “public amusements” on Sundays. Six days was as long as any athletic event could last.

To honor that law, the doors of the Expo opened at 11:00 p.m. on Sunday. Despite the late hour, between three and four hundred people filed in to watch the start of the race. The two competitors drew lots to determine track position: Weston would walk on the inside track, O’Leary on the outside. Shortly after midnight, once the Sabbath had broken, Chicago mayor Harvey Doolittle Colvin addressed the crowd in the dim light of the building’s hissing gas lamps. The mayor’s role announcing the race underscored its magnitude.

From the start, it was clear that O’Leary, seven years younger, was faster. The difference in their gaits was also immediately apparent. According to one observer, O’Leary walked with a “straight form, quick stride, and bent arms.” He held his head up and looked straight ahead. Meanwhile, Weston seemed “rather to drag than throw his feet.” Worse still, the observer bemoaned how he seemed “to carry his head on his breast and to see nothing but the dirt before him.” O’Leary’s crisp form translated into results, and he shot into the lead, completing his first mile in 11 minutes and 3 seconds. It took Weston more than a minute longer.

With no grandstands to watch from, the audience pressed close to the tracks, jockeying for position. Some crossed over to view the action from within the concentric ovals, to the chagrin of the walkers. On several occasions, police had to clear the way for the pedestrians. Even the Chicago Tribune, despite its breathless coverage, seemed stumped by the frenzy. “Walking,” the paper observed, “is at best not an absorbingly entrancing sport.”

But the Tribune was forgetting a basic fact: People were bored. It’s hard to fathom now, but in the 1870s, Americans were desperate for entertainment. As leisure time boomed, most Americans spent their idle hours reading and storytelling, often by candlelight. Live entertainment outside the home—a play, perhaps, or a musical performance—was too pricey to be anything more than an occasional indulgence. (In Chicago, a theater ticket usually cost a dollar, twice the price of a ticket to this weeklong world-class walking match.) Watching people walk in circles for days was, if not “absorbingly entrancing,” at least an unobjectionable way to kill time.

By the end of the first day, Weston trailed O’Leary by 19 miles (110 to 91). Still, he exuded confidence. His strategy was simple: slow and steady. Weston was convinced that fatigue would overcome O’Leary before the race ended. After all, the men got only three to five hours of sleep a night in small rooms in the Expo. For the most part, the two didn’t even stop for meals; more often they ate as they walked. Weston was partial to rare beefsteak; O’Leary preferred mutton and sipped hot tea and Champagne on the move.

When the two pedestrians retired on Tuesday night, O’Leary had added three miles to his lead. By the end of Wednesday night, he had stretched his advantage to 26 miles. It was starting to seem obvious that O’Leary would not wear out as Weston had expected, but Weston was too proud and stubborn to alter his strategy, and he continued to plod forward.

As O’Leary’s lead steadily increased, the Expo overflowed. The audience was packed with Irish immigrants shouting themselves hoarse in thick brogues as they cheered for their compatriot. Those unable to afford the 50-cent admission tried to barter for entry, offering to guard the building’s marble statues in exchange for free admittance.

Finally, as Saturday morning dawned, the outcome no longer felt like a question: O’Leary was ahead, 425 miles to Weston’s 395. By 3 o’clock that afternoon, the line for tickets snaked around the building. That the competitors were by now practically wilting from exhaustion only added to the excitement.

By 9 p.m., 6,000 people had packed into the Expo. “The crowd was motley, but largely respectable,” the Tribune wrote. “It represented wealth, standing, and brains, and thieves, gamblers, and roughs. Ladies were there in large numbers, some with husbands and some with lovers, but all had a terribly hard time of it in the ceaselessly moving and noisy throng.” Small boys crawled through the forest of legs to get close to the action. The older, more adventurous ones clambered up the Expo’s trusses and took seats on the beams near the roof, more than 100 feet above the floor.

As O’Leary neared his goal with each passing mile, a tense murmur moved through the building. Around 10:15, he completed his 495th mile, and it seemed clear that he’d reach 500 well before midnight. Weston, for his part, plodded wearily on.

At 11:15, O’Leary completed his 500th mile. The Expo erupted in delirious cheers. Men threw their hats in the air. The band played a celebratory tune. O’Leary’s wife greeted him at the finish line in front of the judges’ stand with a large basket of flowers. O’Leary paused, caught his breath—and then continued walking. When the hands on the big clock reached midnight, he had completed 503 miles. Weston had clocked only 451.

Both Weston and O’Leary would take home serious winnings: After expenses and a cut for the promoters, each walked away with more than $4,000—nearly $90,000 today. But it was O’Leary’s triumph that was celebrated by every class, from the businessman to the bootblack, as a city that had spurned his people now embraced him as a native son. Newspaper editorials sang his praises. Poets composed verses in his honor. O’Leary’s victory helped the Irish gain some acceptance, if not equality, in Chicago.

O’Leary wasn’t the only outsider who managed to use pedestrianism to break into society. The sport also opened doors for African-Americans and women. After Frank Hart, a Haitian immigrant from Boston, won a prestigious race in 1880, headlines heralded his name from coast to coast, a remarkable achievement at a time when blacks weren’t afforded full citizenship. And people like Ada Anderson (see sidebar) proved that pedestrianism could help women, too, achieve new status levels.

But in some ways, the sport’s greatest legacy was on sports itself: Walking matches marked the beginning of modern spectator sports in America. Never before had so many people attended, and wagered on, athletic events. Never before had the media devoted so much feverish attention to them. The top walkers of the 1870s earned fortunes, not just in prize money but in endorsement deals. O’Leary even shilled for a brand of salt. And men like O’Leary and Weston became celebrated heroes, seeing their images immortalized on some of the first cigarette trading cards, a precursor to baseball cards.

It wasn’t long, however, before America’s new pastime faced some stiff competition. In 1885, the “safety bicycle,” boasting two similar-sized wheels, emerged. The sleek rides made for faster-paced, more riveting races. Around the same time, baseball was on the rise. The National League, founded as a ragtag enterprise in 1876, became a profitable business after team owners reorganized. Spectators who had once flocked to walking matches now filled spacious new wooden ballparks.

By the mid-1890s, pedestrianism was foundering. Charges of race fixing and doping tarred the sport. The great Weston himself was caught chewing coca leaves during a race—a practice many considered unsportsmanlike, if not outright cheating. Public sentiment began to turn, and people realized that six-day races, the most popular form of pedestrianism, were absurd. Instead of being seen as feats of athleticism, they were looked down on as freak shows.

Great walkers like Weston and O’Leary, though, didn’t stop walking, even as pedestrianism faded in popularity. In 1913, a 74-year-old Weston walked from New York to Minneapolis, selling a 10-cent souvenir program along the way. O’Leary became a traveling “baseball pedestrian,” staging exhibitions before games in ballparks across the country. He would challenge one of the ballplayers to run around the bases twice while he walked around them once. More often than most expected, O’Leary won. Afterward, he would pass through the stands, hat in hand, collecting nickels and dimes to subsidize his winters in Southern California.

O’Leary stayed true to the sport till the end. When asked for exercise suggestions for “weakly men and women,” O’Leary’s response was as quick as it was inevitable: walk. “Do not take strolls,” he admonished. “Vigorous breathing is what builds up a healthy life.” He seemed to be on to something: The Irish hero lived well into his late 80s. Old-timers swore that, even as an old man, he still walked “like a piece of machinery.”

Adapted with permission from Pedestrianism: When Watching People Walk Was America’s Favorite Spectator Sport (Chicago Review Press), by Matthew Algeo.