Has a more iconic road ever been built? This year, America’s famous highway turns 100. Route 66 and its fellow numbered roads were revolutionary when the federal highway system was created in 1926. For the first time ever, an ordinary person could navigate across the country without a guide and enjoy the journey for the journey’s sake: the ultimate road trip.
But what made this particular route so legendary? Covering almost 2,500 miles, Route 66 passed through Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California. Depression-era migrants fleeing the Dust Bowl used the Mother Road to head west; a famous footrace on the route, known as the Bunion Derby, captured the public imagination; then a Nat King Cole song and a television show cemented its place in the American psyche once and for all.
As author Michael Wallis says, “Route 66 is Woody Guthrie and Mickey Mantle and Jack Kerouac. It’s thousands of waitresses, service station attendants, fry cooks, truckers, grease monkeys, hustlers, state cops, wrecker drivers, and motel clerks”.
But who was the road really for – and who did it leave out?
A large stretch of it also sold a decidedly manufactured Southwest – “Native American” wigwam hotels; cafés built in the shape of a giant sombrero. Roadside “trading posts” and “snake pits” promising a brush with a Wild West more imagined than real.
Meanwhile, Black travellers were forced to consult The Green Book just to stay safe on the very same route – a compendium of the diners, hotels and gas stations that would actually serve them at a time when segregation and sundown towns made a simple road trip genuinely dangerous.
Then, in 1956 the Interstate Highway Act slowly kills the road. Towns were bypassed in the interest of speed, and businesses die. But in 2026, the myths (and the wigwam hotels) are as alive as ever.
In this episode, Sarah and Jeremiah dive into the romance, the reality, the open road, and everything it leaves unsaid. Plus, we unpack in detail how to do the trip yourself, which car to drive, and why this centennial year might just be the perfect moment to go.
Topics: Route 66 centennial, US highway history, Dust Bowl migration, Jack Kerouac, On The Road, Beat Generation, John Steinbeck, Grapes of Wrath, Nat King Cole, Green Book, Black travel history, racial segregation, Native American representation, Chicano culture, American exceptionalism, Chicago to Santa Monica, Southwest USA travel, Interstate Highway Act.
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