Celebrating 100 Years of Route 66 – Ride the Dream
Riding Historic Route 66 – affectionately known as “The Mother Road” – isn’t just a road trip, it’s a rite of passage. As Route 66 hits its 100-year milestone, there’s no better time to saddle up and experience this living slice of American history on two wheels.
A Road Paved with History
Route 66 was born in 1926, carving a path from Chicago to Los Angeles. It carried dust bowl migrants, wartime convoys, and wide-eyed dreamers chasing the promise of the West. Riding it now is like riding through a living museum — every stretch of tarmac has a story to tell.
Rolling Through Nostalgia
From neon-lit diners and weathered gas stations to vintage motels and rusty old signs pointing to forgotten towns — Route 66 is a time machine that takes you straight into the heart of mid-century Americana. It’s kitschy, it’s classic, and it’s got soul.
Scenery That’ll Steal Your Breath
You’ll ride through the golden plains of the Midwest, into the red deserts of New Mexico, past jagged mountain ranges and sun-drenched canyons. The landscapes shift like scenes in a movie — each more stunning than the last.
A Patchwork of Culture
Every state along Route 66 has its own flavour. You’ll taste the spice of New Mexican enchiladas, hear blues drifting from a Missouri bar, and meet locals with stories that could fill a book. It’s not just a ride — it’s a deep dive into the heart of America.
Weird, Wacky, and Wonderful
Giant roadside dinosaurs. A field of Cadillacs half-buried nose-first in the dirt. A motel made of teepees. Route 66 is full of surprises — some strange, some beautiful, all unforgettable.
The Ride of a Lifetime
Crossing Route 66 on a motorcycle is more than just ticking a box — it’s a personal triumph. It’s 2,400 miles of freedom, grit, and the thrill of the open road. And doing it on the 100th anniversary? That’s something you’ll be telling stories about for years.
So, if the road is calling… answer it.
The Mother Road is waiting. And there’s no better way to celebrate her century of stories than from the saddle of a motorcycle.
| DEPARTURE / RETURN LOCATION | Chicago / Los Angeles |
Map –
ITINERARY WESTBOUND
Day 01: Departure – Arrival Chicago, IL.
Welcome to the Windy City — Let the Adventure Begin!
You’ve just landed in Chicago, the legendary “Paris of the Prairie” — a city that pulses with energy, rhythm, and sky-high style. Nestled on the shores of Lake Michigan, Chicago boasts one of the most iconic skylines in the world, and it’s packed with world-class museums, buzzing cafes, sizzling restaurants, and enough jazz and blues bars to keep your toes tapping all night long.
But tonight, it’s all about kicking off your dream Route 66 ride in style. You’ll meet your fellow road warriors and Tour Guides at our Orientation Meeting at the tour hotel — a chance to connect, share the excitement, and get a taste of what’s to come.
After that? We’re heading out for a fantastic Welcome Dinner to raise a glass to the road ahead. The Mother Road is calling — and this is where the journey begins.
Day 02: Chicago, IL – Springfield, IL (Riding day 1: 300 km / 189 miles)
It’s Go Time — Hit the Road on Route 66!
This morning, it’s all about that sweet moment — you pick up your bike, fire it up, and feel the anticipation crackling in the air. The ultimate American road trip is officially underway.
From the motorcycle pick up location, you roll straight onto the legendary Route 66 — the Mother Road herself — stretching westward from the heart of Chicago all the way to the sun-drenched Pacific Coast.
Today’s ride takes you south along the historic Pontiac Trail, the original ribbon of road that carved this route through Illinois. You’ll cruise through classic towns like Joliet, soak up small-town Americana, and make a must-stop at the incredible Route 66 Museum in Pontiac — a treasure trove of nostalgia and roadside charm.
The road beneath your wheels, the wind in your face, and that unmistakable buzz of freedom — this is the start of something unforgettable.
Day 03: Springfield IL– St. Louis, MO (Riding day 2: 186 kms / 116 miles)
Rolling Into St. Louis — The Gateway to the West Awaits!
Today, it’s time to dive deeper into the soul of Route 66 as we head for the vibrant city of St. Louis. We’ll ride the classic two-lane stretches of the Mother Road, winding through golden cornfields, timeless main streets, and charming small towns that embody the true heart of America.
This is the kind of ride where every mile feels like a step back in time — where diners, vintage gas pumps, and faded signs whisper stories of countless travellers who came before us.
Our approach into St. Louis is nothing short of iconic — we’ll cross the mighty Mississippi River via the historic Chain of Rocks Bridge, the original RT 66 crossing and a true piece of Americana.
Once in St. Louis, get ready to soak up the buzz of this incredible riverside city. Known as the “Gateway to the West,” it’s got it all — legendary live music joints, unbeatable BBQ ribs, and a laid-back energy that invites you to kick back, relax, and let it all sink in.
The road is just getting started — and so is the adventure.
Day 04: St. Louis, MO – Joplin, MO (Riding day 3: 536 kms / 335 miles)
Sunrise Over the Arch, Then It’s Back on the Mother Road
If you’re up for it, rise early and take a quiet stroll across the street for a magical moment — watching the morning sun light up the Gateway Arch and dance across the Mississippi River. It’s a peaceful way to start the day before we fire up the bikes and leave St. Louis in our mirrors.
Soon enough, the city fades behind us, and we roll into the heart of Missouri’s stunning countryside. The landscape shifts into gently rolling hills, winding roads, and postcard-perfect scenes that make this stretch an absolute joy to ride.
We’ll stop for a photo op with the World’s Largest Rocking Chair in Fanning — a true roadside legend — before carving our way through the twists and turns of Devil’s Elbow, one of Route 66’s most beloved bends. Keep your eyes peeled — this road is full of hidden gems and classic Americana waiting to be discovered.
Tonight, we roll into Joplin, a resilient city with a powerful story. In 2011, a devastating tornado left its mark here — and if we’re lucky, we might end the night swapping stories with the locals, hearing firsthand accounts of courage, survival, and the spirit of a community that refused to quit.
Another day down, more memories made — and Route 66 keeps getting better.
Day 05: Joplin, MO – Oklahoma City, OK (Riding day 4: 408 kms / 255 miles)
Cruisin’ Through Oklahoma — Where History and the Highway Run Deep
Today, it’s all about the ride — and this stretch of Route 66 doesn’t hold back. We leave Joplin behind and head west into the wide-open beauty of Oklahoma, riding through rolling hills and classic horse country. The road leads us through the heart of small-town America — places like Miami, Claremore, and Catoosa, each with its own story to tell.
And yes, we’ll make a stop at the legendary Blue Whale of Catoosa — one of Route 66’s most beloved (and wonderfully quirky) photo ops. You just can’t ride past this smiling giant without saying hello.
As we continue, the landscape deepens with meaning. We pass through the ancestral lands and reservations of the Choctaw, Chickasaw, Seminole, Creek, and Cherokee Nations — a region steeped in both beauty and complex history. In the 1830s, this area was designated as “Indian Territory” by the U.S. Government, and many tribes were forcibly relocated here. Riding through this land today is a powerful reminder of the resilience and rich cultural heritage that still thrives here.
Tonight, we roll into Oklahoma City — a city that beats in rhythm with the heart of Route 66. Once we’ve parked the bikes and kicked off our boots, it’s time to explore Bricktown, a vibrant district packed with lively restaurants, buzzing bars, and local shops. Whether it’s a cold drink, some live music, or just soaking up the vibe — it’s the perfect way to wind down after a day on the open road.
Another legendary day behind us. The road ahead? Still full of surprises.
Day 06: Oklahoma City, OK – Amarillo, TX (Riding day 5: 426 km/266 miles)
From Buffalo Trails to Big Steaks — Riding into the Texas Panhandle
This morning, we roll out onto some of the oldest and most storied stretches of Oklahoma’s Route 66 — a road steeped in Wild West history. Long before pavement touched this land, it echoed with the thunder of massive buffalo herds and the clatter of cattle drives along the famous Chisholm Trail.
We’ll follow that historic trail as it winds through the classic frontier towns of Yukon and El Reno, retracing the paths once taken by cowboys pushing herds north to Kansas railheads in the 1860s. It’s a ride through living history, with every mile bringing echoes of the Old West.
One of today’s highlights is our stop at the Route 66 Museum in Clinton — a must-see for any lover of the Mother Road. It’s packed with vintage treasures, stories, and artifacts that capture the spirit of America’s most iconic highway.
After lunch, we cross into the wide-open spaces of the Texas Panhandle, where the sky stretches forever and the road seems to melt into the horizon. This is the southernmost edge of the Great Plains — pure riding bliss.
And if you’re feeling hungry (or brave), we’re offering an optional stop at the legendary Big Texan Steakhouse in Amarillo. Known for its monster-sized steaks and Texas-sized hospitality, it’s your chance to sink your teeth into what just might be the best steak in the Lone Star State — and maybe even take on the famous 72-ounce challenge if you’re up for it!
Day 07: Amarillo, TX – Santa Fe, NM (Riding day 6: 485 kms / 303 miles)
From Texas to the Land of Enchantment — Welcome to New Mexico!
Today, we say goodbye to Texas and ride full throttle into the mystical landscapes of New Mexico, known as “The Land of Enchantment” — and you’ll quickly see why.
But before we cross the state line, there are some iconic stops that no Route 66 adventure would be complete without. First up, the world-famous Cadillac Ranch — a surreal stretch of prairie where a line of classic Cadillacs rise nose-first from the dirt, covered in graffiti and glowing under the wide Texas sky. Bring your spray can and leave your mark!
Next, we roll into Adrian, Texas, the official midway point of Route 66 — exactly 1,139 miles to Chicago behind you, and 1,139 to Los Angeles ahead. A perfect place for a photo, a slice of pie, and a deep breath to soak it all in.
Then it’s on to the ghost town of Glenrio, straddling the Texas–New Mexico border. Stand with one foot in each state, surrounded by the eerie silence of crumbling Route 66 motels and forgotten dreams — a true slice of Americana.
As we cross into New Mexico, the scenery shifts dramatically. You’ll ride into ancient Comanche territory, through a cinematic blend of mesas, mountain passes, wild cactus fields, and pine-covered hills. The air gets crisper as we climb into the High Plains and arrive at our home base for the next two nights — the magical city of Santa Fe.
With its adobe architecture, rich Native American and Spanish heritage, and soul-stirring sunsets, Santa Fe is not just one of America’s oldest cities — it’s one of its most beautiful.
Day 08: Santa Fe, NM (Explorer and fun day)
A Day to Soak in the Soul of Santa Fe
Today is yours to relax, recharge, or dive deeper into the rich culture and adventure that Santa Fe has to offer. With nearly 400 years of history under its belt, this city is a vibrant blend of Native American, Spanish, and Mexican influences — all wrapped in the earthy hues and timeless charm of its signature adobe architecture.
Wander through narrow streets lined with art galleries, colorful markets, and cozy cafes — or venture further out for something a bit more wild.
Feeling adventurous? Ride along the scenic river valley to the ancient pueblo town of Taos, where traditions run deep and the desert meets the sky. Want a sunrise you’ll never forget? Take to the air in a hot air balloon and watch the high desert glow in shades of gold and red. Or maybe it’s time to channel your inner cowboy with a horseback ride along winding mountain or canyon trails — the kind of freedom you can feel in your bones.
Whether you’re sipping coffee in the historic plaza, exploring local art and jewelry, or chasing big-sky adventure, Santa Fe wraps you in a warm, soulful energy that stays with you long after you’ve left.
Day 09: Santa Fe, NM – Gallup, NM (Riding day 7: 433 kms / 271 miles)
From Santa Fe to Gallup — Into the Heart of the Southwest
This morning, we fire up the bikes and ride south toward Albuquerque, New Mexico’s largest and most dynamic city — a vibrant crossroads where the old meets the new, and where the Mother Road intersects with the ancient trails to Mexico. With a third of the state’s population, Albuquerque pulses with culture, color, and desert energy.
We cross the legendary Rio Grande, then turn west — leaving the bustle behind and heading straight into the wide-open beauty of the Navajo wilderness. The landscape begins to shift dramatically — mesas rise like fortresses, red earth stretches to the horizon, and the road carves a path through a land that feels timeless and sacred.
We pass through the village of Laguna, with its adobe homes and ancient roots, then on through Grants, riding alongside the rugged edges of Cibola National Forest. This is classic Route 66 — open skies, lonely highways, and stories etched into the land.
Our destination tonight is the legendary Route 66 town of Gallup, once a bustling railroad hub and still a cultural stronghold for the Navajo and Zuni people. Known for its rich Native American heritage and as a longtime biker haven, Gallup is the perfect place to swap stories, raise a glass, and relax among fellow riders from around the world.
This is the kind of day that stays with you — the road, the views, the sense of freedom. Route 66 just keeps getting better.
Day 10: Gallup, NM – Grand Canyon, AZ (Riding day 8: 453 kms / 283 miles)
From Fossils to the Canyon – A Day of Pure Route 66 Magic
Today’s ride is one for the books — a full-throttle adventure through jaw-dropping landscapes, iconic landmarks, and pure Route 66 legend.
We kick off the day by crossing into Arizona, where the wide-open road leads us straight into the otherworldly beauty of Petrified Forest National Park. This isn’t just any forest — it’s a prehistoric wonderland where ancient trees, turned to stone over millions of years, lie scattered across a desert painted in surreal hues. Take your time here. Walk among the fossils, soak in the silence, and let the timelessness of this place settle into your soul.
From there, we rumble into Holbrook to check out the iconic Wigwam Motel — where “sleeping in a teepee” is more than just a roadside cliché, it’s a Route 66 rite of passage.
Next, it’s a quick detour to Winslow — and yep, we’re stopping to “stand on the corner,” just like the Eagles sang. Snap that classic photo and take in the charm of this little slice of music history.
While most tours call it a day in Flagstaff or Williams, we keep chasing the horizon — riding deeper into the heart of Arizona and skimming just a mile from the South Rim of the Grand Canyon.
And that’s where the magic truly begins.
As evening falls, you’ll be standing at the edge of the world — cold drink in hand, the setting sun spilling gold and fire across one of Earth’s greatest natural wonders. It’s not just a view — it’s a feeling, and one you’ll never forget.
This is Route 66 at its absolute finest — and your adventure is only getting better.
Day 11: Grand Canyon, AZ – Laughlin, AZ (Riding day 9: 410 kms / 256 miles)
Sky-High Thrills & Wild West Vibes – Grand Canyon to Laughlin
If you’re chasing a once-in-a-lifetime moment, this is your chance to see the Grand Canyon in the most unforgettable way — from the sky. Let us know if you’re ready, and we’ll set you up with an exhilarating helicopter flight over the jaw-dropping South Rim. From high above, the canyon stretches endlessly in every direction, a maze of color, shadow, and ancient stone that will leave you absolutely speechless.
Once you’ve soaked in the sheer grandeur from above (or from the edge), we hop back onto the Mother Road and ride west, rejoining Route 66 in Williams, Arizona.
From there, it’s a legendary stretch of old-school Americana — rolling through the quirky town of Seligman, birthplace of the Route 66 revival, past the nostalgic charms of Hackberry and Kingman, and into Oatman, a once-rowdy mining town where wild burros still wander the streets like they own the place (because honestly, they kind of do).
As the desert sun begins to dip, we cruise into Laughlin, our home for the night — a riverside gem nestled along the tranquil Colorado River. With the bikes parked and the day’s dust settling, it’s time to relax, kick back, and relive the highlights over a cold drink, surrounded by desert beauty and good company.
This is Route 66 at full throttle — adventure, nostalgia, and jaw-dropping scenery rolled into one epic day.
Day 12: Laughlin, AZ – Las Vegas, NV (Riding day 10: 206 kms / 129 miles)
From Desert Heat to Neon Dreams – Welcome to Las Vegas!
Today we trade the quiet hum of the open road for the electric buzz of Las Vegas — but not before an unforgettable ride across the Mojave Desert. This morning’s route is a feast for the senses, as we cruise through sun-scorched landscapes where endless skies meet rugged terrain, and the shimmering heat dances on the horizon.
Then comes the Hoover Dam — a true marvel of engineering. As we rumble across its mighty span, take a moment to marvel at the sheer scale of this iconic American landmark. It’s a dramatic entrance into what comes next…
Vegas, baby! A city that needs no introduction. Your time here might be short, but it’s guaranteed to be unforgettable. Whether you’re strolling beneath the neon glow of the Strip, catching a world-class show, testing your luck at the tables, or just soaking in the glitz with a cocktail in hand — this is your moment to let loose.
Take it all in. Recharge your spirit. Because tomorrow, the roar of your engine will once again echo across the desert as we dive back into the magic of Route 66.
The adventure is far from over — and the best is still to come.
Day 13: Las Vegas, NV – Victorville, CA (Riding day 11: 451 kms / 282 miles)
Rolling Into California – The Mother Road’s Grand Finale
Today, we hit a major milestone — our final state on this legendary Route 66 ride: California! And trust us, this stretch is nothing short of spectacular.
We dive into the vast, rugged beauty of the Mojave Desert, where the open road feels like it stretches forever. The scenery is pure cinematic magic — endless horizons, fields of spiky Joshua Trees, towering rock formations, sun-bleached sand, and cacti that stand like sentinels of time. This is the kind of ride that gets into your soul.
We cruise through the ghostly remnants of Amboy and Ludlow, once vital pit stops for road-weary adventurers chasing dreams out West. The quiet here speaks volumes — every weathered sign and abandoned building whispers stories of the past, and you can’t help but feel connected to the pioneers who rolled this same ribbon of asphalt decades ago.
As the sun dips low over the desert, we arrive at our stop for the night — and what a night it will be. Under a wide, starry sky, we’ll come together to celebrate this incredible journey. There’ll be stories swapped, laughter shared, and that unmistakable feeling of “we did it” buzzing in the air.
One last sleep before we reach the end of the road — and the Pacific calling our name.
Day 14: Victorville, CA – Los Angeles, CA (Riding day 12: 199 kms / 124 miles)
End of the Trail – A Grand Finale on the Pacific Coast
Today, the road calls out one last time — and what a final ride it is. We’re headed for the finish line of this legendary journey: the iconic Santa Monica Pier, the official end of Route 66. But before the ocean greets us, there’s one final stretch that might just steal your heart.
We take on the Angeles Crest Highway — 66 glorious miles of twisty, scenic perfection winding through the rugged peaks of the Angeles National Forest. Climbing to over 2,300 meters, this high-altitude playground serves up sweeping curves, pine-scented air, and views that’ll have you stopping just to soak it all in. It’s easily one of the best rides in Southern California — and a dream finale for any motorcycle adventure.
From the mountaintops, we descend into the vast Los Angeles Basin, feeling the shift as we glide into city sprawl, the ocean breeze growing stronger with every mile. And then, like a movie scene come to life — we roll up to the Santa Monica Pier. The “End of the Trail” sign awaits, and as you stand beneath it, the weight of the journey hits: the memories, the laughs, the challenges, the awe.
This isn’t just the end of a road — it’s a personal triumph. One of those rare, unforgettable moments where the journey and destination are equally extraordinary.
Tonight, we gather one last time for a Farewell Dinner — but it’s more than just a meal. It’s a toast to the road behind us, the stories that were written along the way, and the lifelong friendships forged at throttle’s twist.
Here’s to Route 66 — and to living the dream, mile by mile.
Day 15: Departure – Travel Home
The Ride May End, But the Memories Last Forever
Today, our incredible Route 66 adventure comes to a close in the vibrant city of Los Angeles. After all the miles, moments, and magic we’ve shared, it’s time to say goodbye to the open road — at least for now.
But if you’re not quite ready to hang up your helmet, we’ve got you covered. Let us know if you’d like to stay a little longer in L.A. Whether you’re craving sandy beaches, iconic landmarks, or a few more days to soak up that California sunshine, we’ll help make it happen.
Because the end of the road… is really just the beginning of your next great story.
Tour Dates:
| Tour | Start Date | End Date | Book by |
|---|---|---|---|
| Route 66 – 100 years | 09-Apr-26 | 23-Apr-26 | 08-Feb-26 |
| Route 66 – 100 years | 23-Apr-26 | 08-May-26 | 22-Feb-26 |
| Route 66 – 100 years | 30-Apr-26 | 15-May-26 | 01-Mar-26 |
| Route 66 – 100 years | 06-May-26 | 21-May-26 | 07-Mar-26 |
| Route 66 – 100 years | 07-May-26 | 22-May-26 | 08-Mar-26 |
| Route 66 – 100 years | 21-May-26 | 05-Jun-26 | 22-Mar-26 |
| Route 66 – 100 years | 27-May-26 | 11-Jun-26 | 28-Mar-26 |
| Route 66 – 100 years | 28-May-26 | 12-Jun-26 | 29-Mar-26 |
| Route 66 – 100 years | 11-Jun-26 | 26-Jun-26 | 12-Apr-26 |
| Route 66 – 100 years | 18-Jun-26 | 03-Jul-26 | 19-Apr-26 |
| Route 66 – 100 years | 25-Jun-26 | 10-Jul-26 | 26-Apr-26 |
| Route 66 – 100 years | 09-Jul-26 | 24-Jul-26 | 10-May-26 |
| Route 66 – 100 years | 23-Jul-26 | 07-Aug-26 | 24-May-26 |
| Route 66 – 100 years | 06-Aug-26 | 21-Aug-26 | 07-Jun-26 |
| Route 66 – 100 years | 20-Aug-26 | 04-Sep-26 | 21-Jun-26 |
| Route 66 – 100 years | 27-Aug-26 | 11-Sep-26 | 28-Jun-26 |
| Route 66 – 100 years | 02-Sep-26 | 17-Sep-26 | 04-Jul-26 |
| Route 66 – 100 years | 03-Sep-26 | 18-Sep-26 | 05-Jul-26 |
| Route 66 – 100 years | 10-Sep-26 | 25-Sep-26 | 12-Jul-26 |
| Route 66 – 100 years | 17-Sep-26 | 02-Oct-26 | 19-Jul-26 |
| Route 66 – 100 years | 18-Sep-26 | 03-Oct-26 | 20-Jul-26 |
| Route 66 – 100 years | 01-Oct-26 | 16-Oct-26 | 02-Aug-26 |
| Route 66 – 100 years | 15-Oct-26 | 30-Oct-26 | 16-Aug-26 |
Prices (USD) Due to the variable seasonalities we will quote for your departure and requirements.
2 people / 1 vehicle / 1 shared room: Contact us for a price.
2 people / 2 vehicles / 1 shared room: Contact us for a price.
1 person / 1 vehicle / 1 single room: Contact us for a price.
Currency Converter (use this useful tool to quickly convert currency values)
Inclusions and Exclusions.
| INCLUDED | Late Model Motorcycle Rental Bike Model Guarantee Grand Canyon Helicopter Tour 3 – 4 Star Motorcycle Friendly Hotels Fuel on Riding Days Custom Armored Riding Jacket Breakfast on Riding Days Hosted Welcome Dinner Half-Shell Helmet for Rider and Pillion EagleRider Legendary Farewell Party Experienced Multilingual Tour Guide Support Vehicle Equipped for Luggage and Spare Bike Support Vehicle Driver Door to Door Luggage Service On-Road Concierge Custom Tour Completion Patch National Park Entrance Fees Hotel Parking Fees Transportation between Tour Hotel and Ground Supplier’s Locations Toll Fees |
| NOT INCLUDED | Airfare Meals except where specified Anything not listed in “What’s Included” above VIP ZERO Plus Theft & Damage Waiver Supplemental Liability Insurance $300K |
This tour can be taken as a self-ride; contact us for details.
The above should be taken as a guide only as things can change. If you have any questions, please contact us.
Details correct as at 4 June 2025.
RTWMT ref ER