When America Found Itself Ready to Roll, Route 66, Stretching From Chicago to Los Angeles, Was the Road of Endless Possibilities

The country’s “mother road” started out as a way to get from Point A to Point B but quickly became the host of a culture and a symbol of freedom

A road trip today can feel like an industrial affair: You travel 80 miles per hour on six-lane highways, where brightly lit exits deposit you at 24-hour fuel stops and chain motels. Yet not that long ago, Route 66, a two-lane highway, was the height of modernity. “See America’s Wonderland,” crowed 1940s billboards advertising the road, which then represented the fast lane to the future, connecting Chicago to California in a shining example of early interstate travel. 

When cars were new, in the early 1900s, railroads offered the most reliable long-distance transportation. Thoroughfares called “highways” were often unpaved paths along what had once been hunting trails or wagon ruts. Many had poor signage and were prone to washouts—and featured terrifying corners that might be fine for a horse but wreaked havoc on new-fangled motorcars. 

In 1916, the federal government stepped in, passing the Federal Aid Road Act, and offered states money to develop major highways. Then, in 1921, Congress mandated that federal funds be used to connect those roads into an organized interstate system. 

The government push was welcomed by an Oklahoma businessman named Cyrus Avery. A prominent member of the American Association of State Highway Officials, Avery successfully argued that Americans would be best served by improving the tangled yarn of roads running through the Midwest to the coast and building connections between them. On November 11, 1926, Route 66 became an official federal highway. 

But the road was far from complete. Only around 800 miles of the commissioned 2,448 miles between Chicago and Santa Monica were asphalt. The rest were paved with dirt, gravel, bricks or even wooden boards. To hasten completion, Avery organized envoys from the eight states traversed by Route 66 to promote the new highway with advertisements, maps and even a 1928 foot race from Los Angeles to New York City—the latter chosen in hopes of attracting East Coast visitors. The “Bunion Derby,” as it came to be known, took 84 days and reportedly left 144 of its 199 entrants hobbled. Only 55 runners finished, and the winner, Andy Payne, a member of the Cherokee Nation in Oklahoma, used his $25,000 grand prize (around $500,000 today) to pay off his family’s farm—and, fittingly, buy a car. 

Meanwhile, road crews were working their way across what Avery promoted as the “Main Street of America,” and the entire stretch was finally paved by 1938. 

By that time, the Depression had sent Dust Bowl refugees westward along Route 66, as they fled the empty fields of the Midwest for the golden promise of farm work in California. In his 1939 novel, The Grapes of Wrath, John Steinbeck called the highway “the mother road,” evoking the refuge that “Okies” sought—and the route’s role in the birth of West Coast cities. 

When the United States entered World War II, Route 66 became an artery for military transports heading from forts to ports. After the conflict, the highway cruised into its glory days, brimming with families in big-finned Plymouths eager to tour their newly triumphant country. Road-trippers gawked at the brick and glass of big-city Chicago, towering saguaros in Arizona or the crashing waves of the Pacific. America was beautiful. People had money and vacation time. Route 66 was the place to spend it. 

So many travelers hit the road, in fact, that by the mid-1950s, Route 66 couldn’t support all the traffic. Bit by bit, the road was widened or bypassed in favor of new, multilane highways until the old route was officially demoted from its status as a federal highway. In 1985, its stretches reverted to state-controlled byways and county roads. 

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Mom-and-pop establishments began to fade away as the modern world rushed past on new interstates. Sections of the original route were swallowed up by sand or built over as cities expanded. Yet the allure of the route’s gorgeous scenery and 20th-century Americana continues to attract travelers from around the world. It’s still possible to cover several hundred miles on the old road, especially in Oklahoma, New Mexico and Arizona—and even grab a cup of coffee and a slice of pie at a picturesque café. 

In Luther, Oklahoma, the third generation of the Threatt family is working to preserve one historic stop. Allen Threatt Sr. opened the Threatt Filling Station in 1915 to serve Black travelers during the treacherous days of Jim Crow. As the only Black-owned business between two “sundown towns,” where Black travelers were unwelcome, the Threatt became a haven for Black motorists and a site of community for locals, hosting barbecues and ball games on a full-size baseball diamond. 

Much farther west, in the blowing sands of the Mojave Desert, Albert Okura purchased the old railway town of Amboy (population 0) in 2005 and began the painstaking work of restoring its vintage gas pumps and midcentury motel. After Okura’s death in 2023, his son Kyle continued his dream of restoration. “We can’t give up, because if not us,” Kyle Okura says, “then who?”

On a map, Route 66 might look like a mere choppy diagonal line running from Chicago to the Santa Monica Pier. Yet it has helped tell the American story. The road is a living thing, and at every stop, you’ll find its caretakers. 
 

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Road Shows

In these classic movies—brash, gritty, sometimes outrageous—Route 66 plays a starring role

By Brandon Tensley

1. The Grapes of Wrath In this 1940 film, adapted from John Steinbeck’s novel, the Joad family leaves Oklahoma amid the Great Depression and heads along Route 66 toward the promise of California. The New York Times lauded the Dust Bowl migration tale as deserving of a place on a “small, uncrowded shelf devoted to the cinema’s masterworks.”
2. Easy Rider Two men score big in a Los Angeles cocaine deal, then ride toward Mardi Gras in New Orleans. Directed by Dennis Hopper, the 1969 film cast Route 66 as a symbol of freedom and helped push Hollywood onto a new road of its own, ushering in an era when directors with distinct voices and visions began to run the show.
3. Two-Lane Blacktop Starring the singer-songwriter James Taylor and Beach Boys co-founder Dennis Wilson, Monte Hellman’s 1971 cult film tracks a group of young street racers tearing through the Southwest. The movie evokes a bittersweet moment, not long before Route 66’s two lanes were outnumbered by interstate highways.
4. Rain Man In Barry Levinson’s 1988 dramedy, brothers Charlie (Tom Cruise) and Raymond (Dustin Hoffman) travel from Cincinnati to L.A. to claim an inheritance. They follow stretches of Route 66, visiting landmarks like the Big 8 Motel in El Reno, Oklahoma. The journey—to the West and into the past—helps bridge the brothers’ estrangement.
5. Cars In John Lasseter’s 2006 animated film, Lightning McQueen—a talking race car—is headed to an important race but winds up stranded in the fictional town of Radiator Springs, once a major stop on Route 66. He learns of the highway’s bygone greatness. “Cars didn’t drive on it to make great time,” one resident recalls. “They drove on it to have a great time.”