The Legend of Route 66
America’s Highway of Freedom
There’s a road that lives in the heart of every Twisty Rider in America. A road immortalized in song, romanticized in film, and carved into the rugged soul of a free-spirited nation. That road is Route 66, and its story is as legendary as the asphalt it’s built on.
For motorcycle riders, gearheads, adventurers, and dreamers, Route 66 isn’t just a highway — it’s a cultural icon, a symbol of American freedom, and a tribute to the golden age of the open road.
This blog is your deep dive into the legacy of Route 66 — from its gritty beginnings to its evolution into a nostalgic symbol of American pride. Along the way, we’ll explore the road’s history, its most iconic stops, and what it means to ride the Mother Road today.
The Birth of the Mother Road
The year was 1926. America was booming, but the nation’s roads were a patchwork of dirt trails, local byways, and disconnected highways. The car had become king, but getting from Chicago to California was a logistical nightmare.
That’s when U.S. Route 66 was born.
Stretching 2,448 miles from Chicago, Illinois, to Santa Monica, California, Route 66 was one of the original highways in the U.S. Highway System. Its creation wasn’t just a feat of engineering — it was an invitation. An invitation to explore the American West, to seek opportunity, and to live free.
The man often credited with promoting Route 66 was Cyrus Avery, a Tulsa businessman who saw the need for a highway connecting the Midwest to the Pacific Coast. He envisioned a route that would cut diagonally across the country, through rural towns and bustling cities alike — a true cross-section of America.
And he was right. Route 66 quickly became “The Main Street of America.”
An Engine for American Dreams
In the decades that followed, Route 66 became more than a line on a map. It was a lifeline.
During the Dust Bowl of the 1930s, thousands of families from the Midwest — especially Oklahoma, Kansas, and Texas — loaded up their trucks and headed west in search of a better life in California. John Steinbeck called Route 66 the “Mother Road” in The Grapes of Wrath, a name that would stick forever.
By the 1940s, World War II turned the route into a vital corridor for transporting troops and equipment. Then came the post-war boom, and suddenly, Route 66 was alive with neon signs, diners, motor courts, and gas stations.
Americans fell in love with the road trip.
The open road was more than a vacation — it was a declaration of independence. Route 66 gave people the chance to discover America on their own terms. It connected small-town diners to big city dreams and everything in between.
The Rise of an American Icon
By the 1950s and ‘60s, Route 66 was a cultural touchstone. It showed up in TV shows, movies, songs, and postcards. It was romanticized as the quintessential American adventure — gritty, glamorous, and a little rebellious.
“Get Your Kicks on Route 66”
No song captures the Route 66 spirit better than Nat King Cole’s 1946 recording of “(Get Your Kicks on) Route 66.” The lyrics name-check city after city, taking listeners on a musical journey down the road’s full length.
From Chicago to L.A., it wasn’t just a road — it was a rite of passage.
Hollywood and the Highway
In 1960, the television show Route 66 debuted. The show followed two young men traveling the highway in a Chevrolet Corvette, helping strangers, solving problems, and seeking meaning on the road.
It cemented Route 66 as a symbol of youthful exploration and restless freedom.
The Fall and Rebirth of Route 66
But all legends face trials, and by the late 1970s, Route 66 had met its.
In 1956, the Federal-Aid Highway Act launched the construction of the Interstate Highway System. Suddenly, high-speed interstates bypassed the small towns Route 66 had served for decades. Businesses dried up. Motels closed. Communities faded.
By 1985, Route 66 was officially decommissioned.
For a time, the road fell into disrepair, and much of it was lost. But the legend never died.
Thanks to the efforts of passionate historians, preservationists, and freedom-loving riders, Route 66 made a comeback. States began designating parts of the highway as “Historic Route 66,” and tourism surged. Travelers from all over the world — especially motorcyclists — rediscovered the Mother Road.
Route 66 Today — A Living Legacy
Today, Route 66 is both a time capsule and a revival. Riding the route is like stepping back in time while blazing your own path forward.
You’ll pass vintage diners, classic motels with glowing neon signs, kitschy roadside attractions, forgotten gas pumps, and landscapes that haven’t changed in a hundred years.
But most of all, you’ll experience freedom.
For bikers, Route 66 isn’t just nostalgic — it’s sacred ground. It’s the feel of wind on your face as you cruise through America’s soul. It’s rolling through ghost towns and golden deserts with nothing but time and throttle.
Must-See Stops Along Route 66
If you're planning to ride the Mother Road, don't miss these legendary stops:
Chicago, Illinois — The Starting Line
- Start your journey at the historic Route 66 Begin Sign on Adams Street.
- Visit Lou Mitchell’s, a Chicago institution that’s been feeding Route 66 travelers since 1923.
Pontiac, Illinois
- Home to the Route 66 Hall of Fame & Museum.
- Gorgeous murals throughout town celebrate the route’s history.
Catoosa, Oklahoma — Blue Whale
- This giant blue whale by a pond is pure roadside Americana.
- Originally a family attraction in the 1970s, now it’s an Instagram favorite.
Seligman, Arizona — Birthplace of the Revival
- Historic town where Angel Delgadillo, a barber and Route 66 legend, helped kickstart the preservation movement.
- The whole town is Route 66-themed — it’s like walking through a postcard.
Winslow, Arizona — “Standin’ on the Corner”
- Immortalized by the Eagles’ song “Take It Easy.”
- Grab a photo with the statue and mural — it’s a right of passage.
Santa Monica Pier, California — The End of the Trail
- A sign marks the “official” end of Route 66.
- The Pacific Ocean meets the American dream.
The Route 66 Rider’s Experience
If you’re on two wheels, Route 66 delivers the ride of a lifetime. Here's why:
Diverse Landscapes
- From the cornfields of Illinois to the red rocks of New Mexico, to the sun-soaked coast of California — no two miles are the same.
Biker Culture
- Along the route, you’ll find motorcycle museums, biker bars, classic Harley shops, and fellow road warriors ready to swap stories.
- Towns like Kingman, AZ, and Amarillo, TX, are known for their biker-friendly vibes.
Diners, Drive-Ins, and Dive Bars
- Every meal is a chance to experience authentic Americana.
- Try the burgers at Delgadillo’s Snow Cap Drive-In or chicken-fried steak in Oklahoma City.
More Than a Road — A Symbol of America
What makes Route 66 so iconic?
It’s more than a highway. It’s a story of movement, survival, rebirth, and pride. It reflects the American values of freedom, perseverance, exploration, and independence.
It also represents community. Every business owner who reopened a diner, every biker who rolled through a forgotten town, every artist who restored a fading sign — they all helped keep the spirit alive.
Route 66 is about connection — to each other, to history, and to something bigger than ourselves.
Tips for Riding Route 66
If you're ready to hit the road, here are some things to keep in mind:
Plan, But Stay Flexible
- Route 66 isn’t a straight shot anymore. Some parts are dirt, others are detours. Embrace the unexpected.
Grab a Guidebook or App
- Tools like the Route 66 Adventure Handbook or Historic Route 66 mobile app will help you navigate and find hidden gems.
Prepare Your Bike
- Make sure your ride is road trip ready. There are long stretches without service stations.
Be Ready to Take Photos
- You’ll want to remember the neon lights, sunset highways, and chrome reflections.
Prepare Your Gear
- Visit TwistyRider.com to get geared up for the ride of a lifetime.
Why Route 66 Matters More Than Ever
In today’s world of GPS, 5G, and speed, Route 66 reminds us to slow down. To appreciate the journey. To feel the roar of your engine under wide skies.
It’s about experiencing America the way it was meant to be — from a saddle, with your hands on the bars and your heart wide open.
And maybe most importantly, it’s about keeping a piece of American pride alive. Route 66 connects generations. It links cities to towns, asphalt to dreams, and history to the present.
Ride Into the Past, Present, and Future
Route 66 isn’t dead. It’s evolving — just like the spirit of the American road warrior.
Whether you're a lifelong rider or planning your first cross-country trip, Route 66 is waiting. Not just as a destination, but as a symbol. A challenge. A promise.
So pack your saddlebags, fire up your bike, and get your kicks — not just on the pavement, but in the legacy of the road that made America move.
And when you’re ready to gear up for the journey, head over to TwistyRider.com — your one-stop shop for motorcycle apparel, gear and accessories.