Route 66 at 100: The Mother Road, the Bunion Derby and the legends that made America Dream

On November 11, 1926, something that would eventually become an American cultural icon was officially born.
It was called U.S. Highway 66, although nobody could have imagined that those two digits would one day become synonymous with freedom, adventure, rock ‘n’ roll and the romance of the open road.
Stretching approximately 2,400 miles (3,862 kilometres) from Chicago, Illinois, to Los Angeles, California, Route 66 connected eight states: Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California.
But there was nothing particularly glamorous about it in the beginning.
Rather than a modern highway, it was a collection of existing roads, dirt tracks, gravel surfaces, stretches of brick and even wooden-plank sections, assembled into a single transcontinental route. It would take until 1938 for the entire highway to be paved.
Its famous number was almost different, too. During the discussions about America’s new national highway numbering system, Route 66 was initially considered as Route 60. When that designation was assigned elsewhere, alternatives including 62 were discussed. Oklahoma highway advocate Cyrus Avery and Missouri engineer B.H. Piepmeier preferred 66, believing it was catchy, memorable and had a better ring to it. A telegram sent on April 30, 1926, from Springfield, Missouri, expressed their preference for the number. The rest is history.

Avery would become known as the Father of Route 66, while the road itself acquired another, much more affectionate identity: the Main Street of America.
But one of the strangest episodes in its early history happened two years after its official creation, when an ambitious promoter decided that the best way to advertise a new highway was to send nearly 200 men running across the United States.
On March 4, 1928, 199 competitors gathered at Ascot Speedway in Los Angeles for what became known as the International Transcontinental Footrace, or, more memorably, the Bunion Derby.
The mastermind was Charles C. Pyle, a flamboyant sports promoter nicknamed Cash and Carry. He had already made a name for himself representing sporting celebrities, including American football star Red Grange and tennis champion Suzanne Lenglen.
His new project was considerably more ambitious: a coast-to-coast endurance competition covering approximately 3,422 miles (5,507 kilometres), with a $25,000 first prize and an 84-day schedule.
In today’s money, that winning prize would represent close to half a million dollars.
The runners would follow Route 66 from Los Angeles to Chicago before continuing east towards New York City. They were expected to cover extraordinary daily distances, sometimes approaching 40 miles or more (64 kilometres or more), across deserts, mountains, muddy roads and unpredictable weather.
There were no modern running shoes, no sophisticated sports nutrition and certainly no recovery facilities comparable to those available to athletes today.
Pyle even organised a travelling carnival to accompany the competition. Spectators could watch the runners arrive, enjoy entertainment, buy food and encounter bizarre attractions, including a five-legged pig. It was sport, commercial entertainment and travelling circus rolled into one.
Only 55 of the original 199 competitors eventually reached Madison Square Garden on May 26, 1928.
Among them was a young Cherokee runner from Oklahoma, Andy Payne, who had entered the competition with a very personal motivation: saving his family’s farm from financial difficulties. His determination carried him all the way to victory. He completed the race in 573 hours, four minutes and 34 seconds, collecting the $25,000 prize and securing the future of his family’s land.
His story became one of the most remarkable sporting tales of the decade.
Another competitor deserves particular attention. Eddie Gardner, a Black runner from Seattle, was competing in an America still deeply divided by racial segregation. He was among the Black athletes who faced extraordinary risks while travelling through the Jim Crow South. According to historical accounts, Gardner’s victories over white competitors attracted the attention and hostility of the Ku Klux Klan, and he was advised to keep a low profile in parts of Texas. Despite the dangers, he completed the race in eighth place.
The Bunion Derby was physically brutal, socially significant and financially disastrous for its organiser. Pyle had invested enormous sums, and the travelling carnival failed to generate the revenue he had anticipated. Some towns also failed to honour their financial commitments. He eventually struggled with debts and unpaid bills, although he managed to organise a second transcontinental race in 1929.
His financial failure, however, did not mean the project had achieved nothing. The race brought enormous publicity to Route 66 and helped introduce the highway to a national audience.

Yet the Bunion Derby was only the beginning of Route 66’s extraordinary cultural journey.
During the Great Depression, the highway became a lifeline for hundreds of thousands of families escaping the Dust Bowl. Drought, devastating dust storms and collapsing agricultural livelihoods forced people from Oklahoma, Texas, Kansas and neighbouring states to head west in search of work and a better future. Many travelled in overloaded, ageing cars, carrying everything they owned.
This migration gave Route 66 a much darker identity. It was no longer simply a road towards California: for many, it was a road away from hunger, poverty and desperation.
John Steinbeck immortalised this experience in his 1939 novel The Grapes of Wrath, introducing the expression that would become inseparable from the highway: the Mother Road. The novel’s 1940 film adaptation, directed by John Ford, further cemented its place in American cultural history.

But there is another side to its history that is sometimes overlooked.
Route 66 was not equally welcoming to everybody. During segregation, African American motorists faced discrimination, dangerous encounters and towns where Black people were forbidden from remaining after sunset. The Negro Motorist Green Book, first published in 1936 by Victor Hugo Green, became an essential travel companion, identifying hotels, restaurants and businesses where Black travellers could find accommodation and safety. The road represented freedom, but that freedom was far from universal.

And then came the golden age.
After the Second World War, Americans increasingly embraced automobile travel. Families packed their cars, headed west and discovered a new kind of holiday. Route 66 became a world of neon signs, diners, drive-in cinemas, motels with swimming pools, souvenir shops and attractions designed to make motorists stop, even when they had no intention of doing so.
Some of these places became legendary in their own right.

In Amarillo, Texas, the extraordinary Cadillac Ranch features ten Cadillacs buried nose-first in the ground, their rear ends pointing towards the sky. Created in 1974 by the art collective Ant Farm, it became one of the most recognisable roadside installations in America. Visitors are encouraged to add their own spray-painted designs, meaning its appearance is constantly changing.
In Oklahoma, the Blue Whale of Catoosa is another unforgettable sight. Built in the early 1970s by zoologist Hugh Davis as a surprise for his grandchildren, this enormous concrete whale measures approximately 80 feet (24.4 metres) in length. What began as a family playground eventually became one of Route 66’s most beloved attractions.
Arizona offers another surreal experience: the Wigwam Motel, where travellers can sleep inside individual concrete structures shaped like traditional Native American teepees. Meanwhile, the Blue Swallow Motel in Tucumcari, New Mexico, has become famous for its distinctive neon sign and vintage motor-court atmosphere.
These attractions illustrate something essential about Route 66: it was never just about getting somewhere. It was about everything that happened along the way.

The highway also accumulated its fair share of myths, ghost stories and roadside folklore.
Abandoned petrol stations, deserted settlements and old motels have inspired countless tales of mysterious travellers, unexplained noises and ghostly encounters. Places such as Oatman, Arizona, retain the atmosphere of the Old West, complete with wild burros wandering through the streets, descendants of animals once used by miners.
One particularly fascinating historical curiosity can be found inside Petrified Forest National Park in Arizona. It is the only national park in the United States containing a surviving section of Historic Route 66. The original roadbed is no longer a functioning highway, but a line of old telephone poles still marks its path across the landscape. It is an almost haunting reminder of the thousands of motorists who once travelled through the Painted Desert.

Route 66 also acquired a musical identity. In 1946, songwriter Bobby Troup wrote (Get Your Kicks on) Route 66, inspired by his own journey west from Pennsylvania to California with his wife, Cynthia. Nat King Cole’s version became a hit, and the song was subsequently recorded by countless artists, including Chuck Berry, The Rolling Stones and Depeche Mode. Few roads have ever received such an extraordinary musical tribute.

Television contributed to the legend, too.
Between 1960 and 1964, the series Route 66 followed two young men travelling across America in a Chevrolet Corvette, encountering different communities and people along the way. The programme helped transform the highway into an international symbol of adventure.
Its real-world existence, however, was eventually threatened by progress. President Dwight D. Eisenhower’s Interstate Highway Act of 1956 initiated the construction of a modern network of faster, controlled-access highways. Gradually, new interstates bypassed the old towns, diners and petrol stations. Businesses disappeared, settlements declined and entire stretches of the original road were abandoned.
In 1985, Route 66 was officially removed from the United States Highway System.
But something remarkable happened: rather than disappearing from memory, it became even more legendary. Preservation campaigns, local communities, historians and enthusiasts worked to protect its surviving sections and historic buildings. Today, more than 250 buildings, bridges, road alignments and other associated sites are listed on the National Register of Historic Places.

And so, on its 100th anniversary, Route 66 deserves to be remembered for much more than its famous road signs.
It connected communities, carried migrants, created businesses, inspired musicians and writers, hosted extraordinary sporting spectacles and became the setting for countless personal adventures. It also reflected America’s contradictions, its inequalities and its changing relationship with mobility and freedom.
Perhaps the most extraordinary thing about Route 66 is that it was never really a single road. It was a collection of roads, stories, dreams and lives brought together by a number.
One hundred years later, that number still means something.
Get Your Kicks on Route 66.