Kicks on Route 66: My Favourite Southwest States (and Why Chicago Stole My Heart)
Route 66 has always whispered my name, not just as a stretch of road, but as a living, breathing adventure that snakes through the heart of America. As a child, I dreamed of tracing every mile, chasing the stories and legends that danced along its path. When I finally set my sights on Route 66, I discovered that Temple Street runs this journey every two years. Suddenly, my childhood dream had a purpose: to give back, to help sick kids, and to make every mile matter.
I reached out to Temple Street, signed up for the 2022 adventure, and threw myself into planning a fundraiser. The idea of documenting every twist and turn, every sunrise and roadside diner, took hold—I would write a book, with every cent going back to the kids who inspired this journey. I expected excitement, sure, but I never could have guessed how the road would tug at my heart, or how certain moments would leave me changed forever.
Texas, New Mexico, and Arizona—the sun-baked, story-soaked Southwest—captured my imagination in ways I never saw coming. But before I lost myself in the desert heat and those endless, cinematic skies, let me rewind to where it all began: the city that set my heart racing and my journey in motion.
Chicago: Deep in My Heart and Soul
Every great road trip needs a beginning worthy of legend. For me, Chicago was more than just the starting line of Route 66—it was a city stitched into the fabric of my own story. I had lived and worked in the Windy City, and its streets still hum with memories for me. Before it became the springboard for my adventure, it was home, and it still pulls at my heartstrings.
Stepping away from my daily routine and seeing Chicago through the eyes of a wanderer was no small feat. It filled me with a rush of excitement, but also a bittersweet ache, as if I was saying goodbye to an old friend while chasing a new adventure.
Before I set off, I wandered through my favourite haunts—gazing at the mirrored curves of the Bean in Millennium Park, tracing the Gothic lines of the Tribune Tower, and sinking my teeth into a deep-dish pizza at Lou Malnati’s, the taste of Chicago itself. Standing at the corner of Adams Street and Michigan Avenue, I felt a shiver run down my spine. The "Historic Route 66 BEGIN" sign, framed by the city’s iconic skyline, was more than a marker—it was a promise. The perfect send-off, as I turned my face toward the wild heart of the American West.
Route 66 barely brushes the Texas Panhandle for 178 miles, but what a glorious stretch it is. Texas explodes with roadside Americana—quirky, bold, and impossible to forget. Nowhere else will you stumble upon such a wild patchwork of sights and stories, each one begging to be savoured.
* Cadillac Ranch: Ten vintage Cadillacs are buried nose-down in the dirt, covered in decades of colourful spray paint. Bringing a spray can to leave your mark is a Route 66 tradition, often accompanied by live music and festival-like gatherings.
* The Big Texan: No visit to Amarillo is complete without experiencing the spectacle and renowned steaks at this iconic stop. It features the famous 72-ounce steak challenge, where daring diners attempt to eat a free steak if they finish within an hour—an unforgettable experience reCrossing into New Mexico was like tumbling into another universe. The "Land of Enchantment" lives up to its name, with skies so wide they seem to swallow you whole, and mesas and deserts painted in every shade of red and gold. The earth itself blazed beneath my feet, and history whispered from every sun-baked corner.zed a deep red, and history seemed to whisper from every corner.
In New Mexico, Route 66 shimmers with mid-century magic. Cruising down Central Avenue in Albuquerque, I felt like I was gliding through a living museum of neon, each glowing sign a postcard from another era. Yet it was the quieter corners that truly captured me—meandering through old trading posts brimming with handcrafted treasures, glimpsing adobe buildings beside weathered motor courts, and watching the sun melt into the distant mesas at dusk. These moments etched themselves into my memory.
If New Mexico dazzles with neon and mesas, Arizona sweeps you off your feet with its jaw-dropping natural beauty. Arizona lays claim to the longest unbroken stretch of the original Route 66, and you can feel its spirit humming in the air. I lost count of how many times I pulled over, just to drink in the rainbow bands of the Painted Desert or stand in awe among the ancient ponderosa pines of the Petrified Forest, where petrified logs have waited millions of years for someone to marvel at them.
Arizona is a treasure chest overflowing with quirky roadside wonders. My drive through the Black Mountains to Oatman, where wild donkeys wander the streets and nuzzle up to passing cars, was the perfect, unforgettable finale to my favourite stretch of Route 66.
