They don’t make highways like this anymore.
Once the main artery pumping promise and prosperity across the heart of America, U.S. Route 66 has become more than just a road—it’s a myth woven in asphalt, chrome, and neon. From the bustle of Chicago to the shores of Santa Monica, Route 66 stretches nearly 2,500 miles through eight states, each bend whispering stories of migration, reinvention, and the American dream.
To drive it now is to time travel. The interstate system may have buried it in places, but Route 66 refuses to disappear. It lingers in faded roadside signs, half-forgotten diners, restored motels, and the occasional gas station frozen in the 1950s. It’s there in the jukeboxes, the vintage cars, and the pie recipes passed down through generations.
Chicago, Illinois: Where It All Begins
The journey kicks off at the corner of Adams Street and Michigan Avenue in downtown Chicago. From the shadows of skyscrapers, you head southwest, watching the city fade into the farmlands of Illinois. The sky opens up. The pace slows. Suddenly, you’re not just driving—you’re cruising.
Make a stop in Pontiac, Illinois, home to the Route 66 Hall of Fame and Museum. Murals cover the walls of old brick buildings like postcards come to life, each one a love letter to the road and those who’ve ridden it.
Missouri & Kansas: Small Towns, Big Hearts
In Missouri, the road winds through the Ozarks, rolling hills and Mom-and-Pop businesses leading the way. Don’t skip a night in Cuba (yes, Cuba, Missouri), known for its outdoor murals and retro motor courts. In Kansas—the shortest stretch of Route 66 at just 13 miles—you’ll find Galena, a tiny town with a big personality and the inspiration behind Pixar’s Cars.
Oklahoma & Texas: Wide Skies and Roadside Quirks
Oklahoma offers the longest stretch of the route still drivable today, and with it, the deep roots of Americana. You’ll pass through towns like Claremore and Tulsa, where retro motels and restored gas stations evoke an era of big dreams and Buick convertibles.
By the time you hit the Texas Panhandle, you’re in flatland country. Stop in Amarillo for a photo op at Cadillac Ranch—ten vintage Caddies nose-down in the dirt, graffiti-splashed by travelers from around the world.
New Mexico & Arizona: Desert Magic and Vintage Vibes
Route 66 climbs in altitude and beauty through New Mexico’s mesas and red earth. Santa Fe, with its adobe buildings and art markets, offers a soulful pause. As you cross into Arizona, the old road clings to canyon walls and slices through deserts that stretch to forever.
In Holbrook, sleep in a concrete teepee at the Wigwam Motel. In Seligman, grab a burger at Delgadillo’s Snow Cap Drive-In, a place so packed with personality it feels like stepping into a cartoon.
California: The End of the Road
The Mojave Desert tests your endurance before you descend into Southern California. The air warms, the traffic thickens, and suddenly, you’re rolling past palm trees. The journey ends at the Santa Monica Pier, where a small sign reads: “End of the Trail.”
But that’s not true, is it?
Because the end of Route 66 isn’t just an endpoint on a map—it’s a feeling. It’s the echo of rock ‘n’ roll from a dashboard speaker, the laughter of strangers in a roadside café, the hum of tires on hot pavement, and the soul-deep satisfaction of moving forward while looking back.
Route 66 doesn’t take you somewhere. It becomes the somewhere. And once you’ve driven it, it never really lets you go.
Michael J McCluskey 