<p>Route 66, the iconic American highway immortalized on screen, in song, and on the page, turns 100 this year. One writer considers why this stretch of road beckons now more than ever.</p>

<p>In 1946, a songwriter named Bobby Troup decided that to advance his career he had to leave Pennsylvania and head for Los Angeles. He got in his 1941 Buick, bought with the royalties from his hit single “Daddy,” and started on U.S. Route 40 before picking up Route 66 outside Chicago with his then-wife, Cynthia, by his side. On their first day, Cynthia suggested he use the road trip as inspiration for his next song; she even came up with the line <em>Get your kicks on Route 66</em>. Though their journey was, by his account, miserable along many stretches of the winding byway—“It was possibly the worst road I have ever taken in my life,” he once said—Troup had written two stanzas and the melody of “Get Your Kicks on Route 66” by the time they arrived in Los Angeles. Less than a week later, at the Trocadero, he played part of the unfinished song for Nat King Cole, who would ultimately record it. The resulting hit took listeners on a sonic ride through towns like Joplin, Amarillo, Gallup, Flagstaff, and Winona, and went on to be recorded by everyone from Bing Crosby and Sammy Davis Jr. to the Rolling Stones and Depeche Mode. The famous highway would dramatically change the course of Troup’s life, though he had no idea at the time. “I just wanted to tell a story of a trip to California,” he said in a 1985 radio interview. “I certainly didn’t realize I was writing about a legend.”</p>

<p>The legend began in 1926 when U.S. Route 66, which kicks off in Chicago and ends in LA, cruising through eight states along the way, was officially designated by the American Association of Highway Officials. A Tulsa businessman named Cyrus Avery, who was part of the federal government’s effort to turn the country’s meandering road system into something more efficient, is responsible for choosing its now iconic number. The timing was right: twenty years after the first Model T Fords made driving more accessible to the masses, along came a road that beckoned travelers from rural prairie hamlets and desert-bound towns to bustling cities and the majestic coast. In 1939’s Grapes of Wrath, John Steinbeck chronicled the Joad family’s arduous journey from Dust Bowl Oklahoma to California, shining a light on the plight of migrants and workers at the height of the Great Depression. In his story (which became an Oscar-winning film in 1940), he christened Route 66 the Mother Road, a name that has stuck.&nbsp;</p>

<p>But it’s never been just a road. Route 66 has, in the hundred years since its inception, come to represent both redemption and renewal, a passage to adventure and promise and freedom, a long and winding break from reality. And Steinbeck is one of many who have traversed it for inspiration and used it as a backdrop for their own stories. It was a character in Jack Kerouac’s 1957 Beat Generation classic On the Road; photographer Robert Frank crisscrossed it for his seminal book The Americans, and so did Dorothea Lange, immortalizing the<br>Dust Bowl migrants in powerful images that gave Steinbeck’s words a face.</p>

<p>Photographers Stephen Shore, Garry Winogrand, Lee Friedlander, and Edward Keating have all felt the pull of the Mother Road, capturing its desolate expanses, tarnished monuments, and the people who don’t just see it as a passage to somewhere else. On the big screen it has been the setting for a motley array of road-trip movies. In 1969’s countercul-ture classic Easy Rider it symbolized adventure and a middle finger to establishment rules; in 1988’s Rain Man, the site of a slow, emotional transformation between an autistic man and his self-centered Yuppie brother; in 1994’s Natural Born Killers, a killing ground and escape route for a sadistic couple; and in 2006’s Little Miss Sunshine, a venue for a family to work out their dysfunctions while crammed into a VW bus heading to a child beauty pageant.</p>

<p>Though Route 66 was officially decommissioned in 1985, disappearing from modern maps as newer interstates gradually replaced or bypassed the original road, it’s still there if you seek it out. Some of its most rewarding and drivable sections remain in Arizona, New Mexico, Oklahoma, and Missouri, where the original stretches of road, roadside attractions, and historic towns continue to entice. There’s the Art Deco Conoco Tower Station and U-Drop Inn Café in Shamrock, Texas, built in 1936 and restored to its former glory in the early 2000s; the abandoned ghost town ruins of Two Guns, Arizona; the iron and concrete blue whale of Catoosa, Oklahoma, erected by a zoologist as a gift for his wife in 1972; the geodesic dome in Meteor City, Arizona; the 90-foot-tall sculpture at Chelsea, Oklahoma’s Totem Pole Park, lovingly carved and erected by Ed Galloway; the first Phillips 66 gas station, a quaint, dollhouse-style cottage in McLean, Texas; the neon sign of the Blue Swallow Motel in Tucumcari, New Mexico; and the Threatt Filling Station in Luther, Oklahoma, the Route’s only known Black-owned and -operated gas station and a safe haven for Black travelers during the Jim Crow era.&nbsp;</p>

<p>As many road-trippers, eager for efficiency, have detoured to the interstate, the passage of time and progress has left stretches of Route 66 weary, an aging symbol of Americana. The appeal of traversing it now is largely nostalgic, a meandering lens on bygone eras, a chance to, as Beck sang, Put your hands on the wheel/Let the golden age begin.</p>
<p>Considering our travel plans are increasingly predetermined by algorithms and performed for future social media posts, the chance to rewind the clock feels especially enticing. Our culture has shifted dramatically in the hundred years since the road’s christening, but for writer and historian Michael Wallis—the premier chronicler of Route 66’s wonders and author of Route 66: The Mother Road—its story is far from over. “It’s just still really the beginning for Route 66 because it’s an unfinished road,” he told Oklahoma Today earlier this year. “It’s always been—and always will be—a work in progress.” And there’s nothing more emblematic of America than that.</p>

<h2 style="text-align: center;">Off Roading</h2>

<p>These hotels put you within reach of Route 66’s surviving stretches, from Arizona's landscapes to detour-worthy destinations between Chicago and LA.</p>

<h4 style="text-align: center;">Palmer House, a Hilton Hotel, Chicago</h4>

<p>The oldest continuously operating hotel in the country (it officially opened its doors in 1873 after the original building burned down in 1871) was a grand gift from businessman Potter Palmer to his new bride, Bertha. She would go on to amass the largest collection of Impressionist art outside France, while the hotel, whose common spaces retain a whiff of its storied past, is credited with creating one of America’s most popular desserts: the brownie.</p>

<h4 style="text-align: center;">The Inn of the Five Graces,&nbsp;Santa Fe, New Mexico</h4>

<p>At the inviting, adobe-style hotel in Barrio de Analco, the oldest neighborhood in the country, each suite is a universe unto itself, lovingly decorated and entirely unique. At the<br>gorgeous spa on-site you can bookend your deep-tissue massage with meditation or a clairvoyant reading.</p>

<h4 style="text-align: center;">La Posada, Winslow, Arizona</h4>

<p>When La Posada first opened in 1930, Mary Jane Colter designed it with a specific vision in mind: a grand hacienda for a wealthy Spanish landowner. While the hotel was shuttered for many years, it got its own revival in the 1990s—as did the surrounding gardens, home to many sustainable desert plant</p>

<h4 style="text-align: center;">L'Auberge De Sedona,&nbsp;Sedona, Arizona</h4>

<p>Take a 45-minute detour from the route to reach this tranquil retreat, nestled amid canyons, creeks, and towering red rocks, with the landscape best admired from the cliffside heated pool or through the floor-to-ceiling windows of the resort’s cliffside suites.</p>

<h4 style="text-align: center;">High Country Motor Lodge, Flagstaff, Arizona</h4>

<p>Opened in 1962 as a roadside motel, the property has been transformed in recent years into a boutique hotel while retaining much of its retro charm—including cassette decks&nbsp;in each room, complete with curated mixtapes. Book one of the cosmic cottages and take in the stars from the pool.</p>

<h4 style="text-align: center;">Hotel El Rancho,&nbsp;Gallup, New Mexico</h4>

<p>Charm of yesterday…convenience of tomorrow. Those words are emblazoned beneath the neon sign at El Rancho, which opened in 1936, founded by the brother of film director D.W. Griffith. The iconic Route 66 hotel has played host to countless Hollywood headliners over the years, with many of its rooms—like the John Wayne or the Marx Brothers Suite—named in their honor</p>

<h4 style="text-align: center;">The Barfield Hotel,&nbsp;Amarillo, Texas</h4>

<p>Amarillo’s first skyscraper was erected in 1927 by Melissa Dora Oliver-Eakle, who went by her initials, M.D., to disguise the fact that she was a female builder. The structure remains, while the interior has been transformed into a modern boutique hotel.</p>

<h4 style="text-align: center;">Boots Court, Carthage, Missouri</h4>

<p>Staying at this 13-room roadside motel feels like the best kind of time travel, and it should, considering it’s one of the oldest in operation on the entire route. If you need something to remember your stay, an on-site shop offers souvenirs aplenty.</p>

<h4 style="text-align: center;">Hotel Figueroa, Los Angeles</h4>

<p>This Spanish Colonial–style hotel in downtown LA shares a centenary birthday with the route itself. Spearheaded by Maude N. Bouldin, the country’s first female hotel manager,<br>it originally opened as a women-only hostel in 1926. To cap off a long journey, book the Rest &amp; Recovery suite, outfitted with the latest in sleep, fitness, and wellness technology.</p>

Inside Route 66's illustrious History

Tags

Related Articles

Pop culture

The New Americana: How Artists of Color Are Reclaiming the Old Frontier

Fashion Week

Tommy Hilfiger Takes the Plaza With a Looser Kind of Americana for Spring/Summer 2027

Travel & Living

11 Haunted Hotels in America to Visit

Recommended posts for you

Fashion

See All Of The 2026 CFDA Fashion Awards Winners

Fashion

How Diotima's Rachel Scott Blends Jamaican Heritage With Sustainability

Fashion

All The Best Looks From The 2026 CFDA Fashion Awards

Fashion

Le Patina Prince: Inside Berluti’s Artful Tribute to Le Petit Prince

Travel & Living

Inside Route 66's illustrious History

Fashion

Spring/Summer 2027’s Accessories Have Main Character Energy

Men's

Jude Bellingham Ditches His Jersey for a Pair of Calvins

L'Officiel Art

What to See at Salon Art + Design 2026