Riding the Dream: 13 Days on Route 66
I took the challenge: 13 days, 8 states, and 2,400 miles on two wheels. Here’s why this is a journey everyone should take at least once in their lifetime.
Day 1 – Rolling out from Chicago The adventure began in Chicago, a city of deep-dish pizzas and jazz-soaked streets. The anticipation in the group was palpable as we revved our engines and pointed west. Route 66 signage appeared early and often—nostalgic relics of a golden age. Every mile we clocked felt like peeling back history.
The Route Unfolds: From Farmland to Desert The days that followed took us through an evolving landscape that felt like flipping through the pages of an American storybook. Illinois gave way to Missouri’s green pastures, and Oklahoma introduced vast, open skies.
In Texas, the Cadillac Ranch offered a surreal photo stop—classic cars half-buried in the dirt, splashed with graffiti and glory. Every state brought something unexpected, whether it was a legendary roadside diner or a dusty ghost town where time had simply stopped.
By the time we reached New Mexico and Arizona, we were immersed in the desert experience. Red rock formations towered on either side of the road. Heat radiated from the asphalt. And yet, the ride was thrilling—pure freedom framed by panoramic beauty.
We passed through towns that looked like old movie sets. Williams, Seligman, Holbrook. Places where Route 66 lives on not just as a road, but as a community. There’s pride in the signs, the murals, and the friendly faces who still greet bikers with a wave and a cold drink.
Nevada’s Neon to California’s Coast Las Vegas hit us like a neon thunderbolt—loud, bright, and utterly outrageous after so much desert quiet. We traded cacti for casinos, dust for dazzle. But the road called us onward, and we left the Strip behind to plunge into the Mojave Desert.
What surprised us was how alive the desert felt. Joshua trees twisted into the sky. Cactus forests stood like sentinels in the heat. And boy, did it get hot. One thermometer read 100°F at Roy’s Motel & Café—where an ice cream was less a treat and more a necessity.
We pushed west through the barren beauty, stopping at the iconic Bagdad Café (yes, from the movie) and the quirky Bottle Tree Ranch—one man’s dream turned folk-art installation. It’s impossible to see these places and not feel part of something bigger, something storied.
Day 13 – The Final Push to Santa Monica The last day was a blur of emotion. The road twisted through mountain passes and onto Sunset Boulevard. For the first time, the scent in the air was floral, not dusty—roses from manicured LA gardens.
Then came Ocean Boulevard. Then the beach. Then, finally, Santa Monica Pier.
We had made it. 13 days. 8 states. Dozens of towns. A thousand conversations. Hundreds of photos. Countless memories. We parked the bikes and looked out at the Pacific Ocean, a shimmering blue full stop at the end of a sentence we’d been writing one mile at a time.
We were exhausted. Sunburnt. Wind-whipped. And absolutely elated.
Why You Should Do It Too This trip isn’t just about riding a road—it’s about living the journey. It’s about disconnecting from deadlines and reconnecting with the open road, the people who still wave from porches, and the landscapes that humble you with their vastness.
Route 66 offers the perfect mix of thrill and reflection. You’ll have high-octane days on winding roads, and quiet mornings with coffee watching the sunrise over the desert. You’ll stay in vintage motels, swap stories with fellow riders, and discover what happens when the journey becomes the destination.
Whether you’re a biker chasing the perfect ride or a traveller looking to walk in the footsteps of history, this experience delivers far more than just a tick on a bucket list. It changes you.
What’s Included? The tour is fully supported—no worrying about logistics. Your luggage is transferred daily, accommodations are pre-booked, and the route is expertly curated to give you the full flavour of Route 66, with time for iconic stops and hidden gems alike. Ride your own bike or rent one locally—either way, everything is taken care of.
You don’t need to be a hardcore motorcyclist to join—just someone with a spirit of adventure and a love of the open road.
Ready to Ride the Legend? If you’ve ever dreamed of experiencing the USA’s most iconic road trip, now’s the time. Route 66 isn’t just a journey—it’s a rite of passage. And I’ll help you make it a reality.
Contact me today to reserve your place. Let’s make your Route 66 dream ride the next story you tell.
