What’s the ultimate American road trip? A Route 66 road trip, of course! This legendary highway, spanning eight states and nearly 2,500 miles, is packed with history, quirky roadside attractions, and stories that refuse to fade. If you’re ready to hit the open road, here’s everything you need to know before you chase the magic of the Mother Road.
Last September, I finally checked a dream trip off my bucket list: driving all 2,448 miles of Route 66 from Chicago to Santa Monica. While I’d tackled smaller stretches of the route over the years, this was my first time going all in, start to finish. Carving out three weeks for such a trip isn’t easy for most Americans, myself included, but the stars aligned, and I hit the road with my newly retired, 70-something-year-old dad for what turned out to be the adventure of a lifetime.
Whether you’re planning to take on the entire route or just a section, Route 66 offers something truly special — a blend of history, nostalgia, and quirky roadside surprises that you won’t find anywhere else. The Mother Road may no longer be the bustling artery it once was, but its charm is undeniable. Before you set out to experience this American icon, here’s what you need to know to make the most of the journey.
Have You Driven Route 66?
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Pack a Map or an App
Navigating Route 66 isn’t as straightforward as plugging it into your GPS and hitting “go.” Since the ghost highway was decommissioned in 1985, drivers must piece together the route like a treasure map. To stay on track, you’ll need some solid navigation tools.
The Route 66 Navigation app became my digital sherpa, while McClanahan’s guidebook served as the wise historian I needed when the app inevitably decided to take a coffee break in the middle of nowhere.
Route 66 is constantly evolving. And, with the centennial celebration just around the corner in 2026, some landmarks are getting fresh makeovers while others fade away. No single map or guide will cover everything, so having at least two resources in your arsenal is the best way to make sure you don’t miss a thing.
Drive When the Sun’s Up
Route 66 truly comes alive during daylight hours. From shifting landscapes to crumbling mid-century motels to quirky roadside attractions, the magic of the Mother Road is easiest to spot when the sun is in the sky. Daytime driving makes it easier to take in the sights and helps you avoid missing blink-and-you’ll-miss-them gems tucked along the route.
Back in its prime, Route 66 was a neon wonderland, with glowing signs lighting up the night like a technicolor dream. Many iconic lights have gone dark these days, but their weathered charm still shines brighter during the day.
Don’t Rush Through the Midwest
With the rugged landscapes and iconic landmarks of the West calling your name, it’s tempting to press the pedal to the metal in Chicago like you’re racing to the finish line. But don’t let the Midwest be just a blur in your rearview mirror. This stretch of Route 66 is packed with charming small towns, lovingly restored roadside treasures, and enough history to keep you intrigued for days.
Driving 200 miles in Illinois is nothing like cruising 200 miles in New Mexico. The Land of Lincoln has preserved much of the original route, adding historic signs, way stations, and quirky roadside attractions to make the journey unforgettable. You could easily spend four or five days exploring Illinois, soaking up its character and history — and still wish you had more time.
New Mexico, on the other hand, is a different story. Much of the route there has been absorbed by I-40, turning a scenic journey into a highway dash. At 75 mph, staring at the back of a semi, those 200 miles will vanish in just under three hours — along with many of the stops that make Route 66 so special. So, take your time in the Midwest. You’ll thank yourself later!
Respect the Signs
On Route 66, “No Trespassing” and “Keep Out” signs aren’t just suggestions — they’re rules to live by. That charming old gift shop? It might be someone’s home. The crumbling motel that’s begging you to explore? It could be unsafe or the unexpected residence of a very territorial raccoon. Even if it looks like no one is around, you should expect that structures with signs are being monitored.
In Grants, New Mexico, a man yelled at me for taking pictures from the sidewalk of a once famous, now rundown hotel listed in every Route 66 guidebook. In Missouri, as I stood on the curb of a public road photographing an old teepee-shaped gift shop with an open sign out front, a woman emerged yelling at me to get away from her property. As I climbed back into the car after photographing an old hotel from the public side of a no-trespassing sign, a pickup truck with a community watch decal appeared and watched us drive away. Expect the unexpected and tread lightly.
Connect with the Locals
Although Route 66 is no longer an official road, it’s a living, breathing storybook — and the locals are its best storytellers. Strike up a conversation, and you might uncover nuggets about the highway’s glory days, tips on hidden gems, or updates on preservation projects you’d never find in a guidebook.
If you’re lucky, you might meet someone who inspired one of the characters in Pixar’s Cars or get the scoop on a soon-to-open roadside attraction that will become the next must-see stop. Whether it’s a diner owner reminiscing about the golden age of road trips or a preservationist sharing their passion, the people you meet along the way can turn your Route 66 journey into something truly unforgettable.
A Route 66 Road Trip Requires Endurance
Tackling all 2,448 miles of Route 66 isn’t exactly a casual Sunday drive. The journey demands stamina, especially if you stick to the original road instead of the interstates. Even as a seasoned road trip enthusiast — with my dad taking the wheel for most of the driving — I was completely wiped out by the time we reached Santa Monica.
If carving out three weeks for the entire trip feels impossible, don’t sweat it. Breaking the journey into smaller sections over time is a great way to soak it all in without burning out. After all, Route 66 isn’t just about the miles — it’s about the experience.
A Road Trip for the Generations
Route 66 sparks nostalgia. It conjures up images of kids packed into station wagons, off to see the Grand Canyon or Disneyland during the golden age of family road trips. Traveling the route with someone who remembers America before the Interstate Highway System adds an entirely new layer to the experience.
During our 2,448-mile journey through eight states, my dad vividly remembered watching America’s highways evolve. He recalled the first stretch of Eisenhower’s interstate highway project opening along I-70 just west of Topeka when he was a kid. Although it wasn’t part of Route 66, it was fascinating to hear how this concrete web reshaped the country.
He also reminisced about staying at his first Howard Johnson’s, marveling at the 24-hour room service, the standardized menu, and the novelty of a motel swimming pool. Stories like these didn’t just bring the history of the road to life — they made the journey personal, adding layers of connection to the Mother Road’s past.
You’ll Probably Want to Drive Route 66 Again
Even though Route 66 was officially decommissioned more than 40 years ago, it’s far from frozen in time. Each year, some abandoned buildings crumble further into history, while restoration projects breathe new life into others. With the centennial celebration just around the corner, organizations like the National Trust for Historic Preservation and the U.S. Route 66 Centennial Commission are working to ensure the Main Street of America continues to captivate travelers for generations to come.
The End of the Trail
Standing at the Santa Monica Pier, watching the sun sink into the Pacific, I realized that Route 66 isn’t just America’s longest decommissioned highway — it’s the country’s greatest storyteller. Whether you’re driving the entire 2,448 miles or just exploring a single section, a Route 66 road trip is an incredible experience. Take your time, soak in the history, and enjoy the experience at your own pace. And, don’t be surprised if you’re already dreaming of a second trip before you’ve even finished unpacking!
Have You Driven Route 66?
Have you driven all or part of the Mother Road? What was your favorite part of the drive? Any additional tips and tricks to pass along? Share your experiences in the comments section below.
Portions of this article originally appeared on Food Drink Life.
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I had two old buddies of mine from Germany who decided to do a good stretch of it in a rented Mustang. Their biggest complaint: No alcohol! No watering holes! They were used to end each day with a good drink. That was hard to find!
Interesting! My Dad and I didn’t have any trouble finding a cold beer or glass of wine at the end of the day with one exception — the night we stayed in Peach Springs. No alcohol was allowed at this Native American hotel, not even something purchased elsewhere.