Route 66: The Classic American Road Trip Adventure – Chicago, Illinois to Santa Monica, California

Hey All:

Buckle up, all, because we’re about to hit the road on a great American journey, cruising down the legendary Route 66. This isn’t just any road trip; it’s a drive through the very heartbeat of America, where each stretch of road and some diners have a tale to tell. Known as the “Mother Road,” Route 66 is filled with beauty, and our Route 66 Itinerary will help you uncover all the hidden gems and stops. 

What is Route 66?

Alright folks, before we get this Route 66 party started, let me give you a quick history lesson on the Mother Road herself.

Route 66 was one of the original highways in the U.S. interstate system back in the 1920s. This iconic 2,400-mile route started in downtown Chicago and stretched to Santa Monica Pier in California. It earned its “Mother Road” nickname because it allowed countless folks to migrate west during the Dust Bowl days, giving birth to a whole new era of roadside Americana.

For decades, Route 66 was the main artery for roadtrippers crisscrossing this beautiful country of ours. Motels, diners, gas stations, and quirky roadside attractions popped up all along the route to cater to these adventurous travelers. Places with names like Radiator Springs from the Cars movies!

While the interstate highway system eventually bypassed and replaced much of the original Route 66, big portions of the Mother Road still maintain their classic Americana charm and nostalgia today. Driving it is like taking a living journey through an iconic slice of 20th-century America.

Whether you’re a seasoned road tripper or just an armchair traveler tagging along through my videos, Route 66 offers a glimpse into an era of simpler times and epic cross-country adventures. So tighten those seatbelts and join me as we cruise the legendary Mother Road!

Kicking Off Route 66 in Chicago:

Chicago is where our Route 66 adventure begins, and it’s the perfect jumping-off point for the Mother Road. This windy city of soaring skyscrapers and a booming metropolitan heart was the original eastern terminus when Route 66 was established back in 1926.

You see, the whole purpose of building this iconic highway was to connect the cities of the East to the wild, untamed West. Chicago represented the gritty industrial powerhouse ready to spread its influence westward across the country. So it made sense to plant Route 66’s starting line right here.

As we depart the urban jungle of Chicago, you’ll immediately feel that palpable shift as the high-rises fade into the horizon. The landscape opens up, and suddenly we’re transported from the hustle of the present day into a nostalgic world where past and present intertwine.

Those first few miles leaving the city are like ripping open a timewarp, giving you a taste of what lies ahead – a winding path of pure Americana where you’ll bear witness to how this ribbon of road transformed little slices of the country into thriving towns and roadside wonders.

One of the first sights to welcome you is Lou Mitchell’s Restaurant in downtown Chicago. This diner has been dishing up hearty meals to road-trippers since 1923, becoming one of the original stops along Route 66’s journey. Can’t you just imagine parking your Model T out front for a plate of hot cakes before ambling back onto Mother Road?

One of the first stops on Mother Road is Lou Mitchell’s Restaurant in downtown Chicago.

Rolling Through Missouri: 

When you drive into Missouri, the road takes you through the rolling hills of the Ozarks.  Here, Route 66 starts to show you vintage motels and neon signs lighting up the way. It’s like driving through a living museum. In these small towns, you can feel the Mother Road in every mile. 

Oklahoma’s Timeless Trail: 

As you cross state lines into Oklahoma, the route becomes a time capsule of the classic  American road trip. You will pass through towns where antique shops and old gas stations have stood the test of time, offering a glimpse into the life of the road in its heyday. It’s here that Route 66 gets under your skin. 

Midpoint Cafe got its name because it’s the geographic midway point between Chicago and Los Angeles on historic Route 66 — both cities are 1,139 miles away from the cafe

Southwest’s Rugged Beauty: Arizona and New Mexico

Now, prepare yourself for one of the most dramatic shifts in scenery as we cross over into the Southwest and cruise through Arizona on Mother Road. The air turns dry and crisp, and the landscapes take on an entirely new complexion of rugged, desert beauty.

As you roll across that state line, it’s like entering a completely different world. The flat prairies give way to towering mesas and iconic sandstone formations that seem plucked straight from an old Western film. Route 66 winds and dips through this wonderland, hugging the contours of a land sculpted by eons of elemental forces.

One of the first stops that will give you a true taste of Arizona’s Route 66 magic is the sleepy town of Seligman. This is your chance to hop off the Mother Road and immerse yourself in a trip back in time. 

From Seligman, make your way west towards Oatman – a legitimate ghost town brought back to life by Route 66’s rebirth. As you approach, keep an eye out for the iconic “burros” (wild donkeys) that wander the streets.

No Route 66 journey through Arizona would be complete without a pilgrimage to Kingman. This Route 66 town offers a vibrant mix of classic Americana stops and natural splendor. Be sure to consult my “Kingman AZ Top 5 (Route 66) Must See Locations” for the can’t-miss highlights like the Hackberry General Store.

But no matter which of the legendary Arizona stops you visit, one thing is certain – the Southwest’s rugged majesty and rich history will get seared into your soul as the iconic Route 66 adventure unfolds.

Now, prepare for a big shift as you hit the Southwest. The air gets drier, the landscapes more dramatic, with deserts stretching out as far as the eye can see. In Arizona and New Mexico, Route 66 takes on a wilder, more rugged view, winding through beautiful landscapes. The desert and towering mesas are not just beautiful to see; they’re only some of the sights of the American West. 

Two Must Stop Attractions:

Check out the pictures below. These are 2 MUST-STOP places to check out while traveling  Route 66 in Arizona. Both places are located approximately 33 miles from Kingman, AZ.

Iconic Stops and Attractions:

Don’t forget the iconic stops along the way – the trading posts, the roadside attractions,  and the diners that have been serving travelers for generations. Each stop is a chance to stretch your legs, grab a bite of classic American fare, and chat with locals, whose stories add interest to your journey. From the world-famous Cadillac Ranch to the meteor craters and ghost towns, these are the places where Route 66 comes alive, where the history of the road becomes real. 

California Dreaming:

As you get to the end of your Route 66 adventure, California has some beautiful ocean views and a different pace of life. Cruising down the final stretch toward Santa Monica, the landscape changes, and you can see the Pacific Ocean on the horizon. When you get to the pier, that’s where the historic route officially ends.

The Essence of Route 66:

But Route 66 is more than just the places you will see or the road beneath your wheels; it’s about the journey itself, the freedom of the open road, and the stories you will gather along the way.  It’s also about the people you will meet and the shared experience of traveling a road that has a history.

So there you have it……. a road trip down Route 66, is not just a travel journey, but a journey through American history, culture, and the beauty of the landscape. It’s a trip that shows you the real America, the small towns, the big cities, and everything in between. 


In the end, Route 66 isn’t just a road; it’s a journey into the heart of America.  That’s what makes it the ultimate American road trip – a journey that’s as much about discovery as it is about destination, as much about the past as it is about the present. It’s a road that tells a story, and you can’t wait to share every mile, every story, and every unforgettable moment of this journey with your friends and family.  If you would like to see my Route 66 videos, head to RVerTV YouTube and do a search on  Route 66.

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