What makes a Route 66 road trip the ultimate American adventure? Maybe it’s the sheer nostalgia of cruising a legendary highway or the thrill of uncovering quirky roadside gems you won’t find on a GPS. Whatever draws you to it, here’s everything you need to know before you chase the magic of the Mother Road.
Last September, I crossed a huge item off my bucket list. While I’d driven many sections of Route 66 over the years, I had never tackled the entire 2,448 miles from Chicago to Santa Monica in one go. For most Americans, carving out three weeks of vacation to make the end-to-end journey is nearly impossible (me included), but this time, the planets aligned, and I set out with my recently retired, 70-something-year-old father for the experience of a lifetime.
Whether you’re planning to drive the full distance or explore just a stretch, Route 66 offers a blend of history, adventure, and nostalgia unlike any other road trip. Although it’s no longer the bustling highway it once was, The Mother Road’s stories, sights, and quirks still capture the imagination. Before you hit the road, here’s what you should know about navigating America’s most iconic highway.
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Have You Driven Route 66?
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Take a Map or an App
Route 66 isn’t your typical road trip. You can’t just press “start” on your GPS and get turn-by-turn directions. Officially decommissioned in 1985, this ghost highway has stretches that have either disappeared completely or been absorbed by modern highways. Finding your way along the Mother Road is more like solving a puzzle, and you’ll need the right tools to put it together.
For my Route 66 road trip, I primarily relied on the Route 66 Navigation app and the beautifully detailed Here It Is! Route 66 Map Series by Jim Ross and Jerry McClanahan. When my app decided to take a break (as they tend to do in the middle of nowhere), McClanahan’s EZ66 Guide for Travelers became my lifesaver, offering old-school maps and helpful tips.
It’s important to remind you that Route 66 is a living, evolving (although decommissioned) highway. As the 2026 centennial approaches, restoration projects are reviving some landmarks while others quietly fade into history. No single resource will capture everything, so your best bet is to arm yourself with at least two guides — one for real-time navigation and one for context.
Drive During Daylight Hours
The shifting landscapes, vintage roadside attractions, and crumbling relics of Route 66’s golden age are far easier to spot during the day. Driving between dusk and dawn lets you take it all in — quirky neon signs, crumbling motels, and all sorts of hidden gems that would otherwise be missed.
Back in its heyday, Route 66 lit up the night like modern day Las Vegas, with glowing signs guiding travelers from diners to motels. Today, most of those lights have dimmed, their tubing either removed or left to the elements. While their nighttime charm has faded, those same relics look stunning in the natural light, where their details and weathered charm stand out. To truly soak in the Mother Road, stick to daylight hours — it’s when the road is most alive.
Don’t Rush the Midwest
When you think of Route 66, your mind may immediately fill with dramatic dessert landscapes or the bustling Santa Monica Pier. But don’t leave Chicago in your dust and race toward California. Route 66’s Midwestern stretch is brimming with charm, history, and some of the most lovingly preserved spots on the entire route.
Route 66 in Illinois is a treasure trove for Route 66 enthusiasts. From historic signs to quirky roadside attractions, the state has poured resources into preserving its section of the Mother Road. You could easily spend four or five days just in the Land of Lincoln, exploring its small towns, snapping photos of restored landmarks, and soaking in the nostalgia of a bygone era. By contrast, New Mexico’s stretch of Route 66 can feel like a blink-and-you-miss-it highway dash. Much of the road has been swallowed up by I-40, with far fewer stops to break up the miles.
Respect the Signs
You should always respect no trespassing, keep out, and private property signs — and Route 66 is no exception. An abandoned motel or gift shop listed in a guidebook may now be a privately owned residence. Crumbling structures may be unsafe to explore, and they may serve as shelter for unhoused people or territorial raccoons. 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 on it appeared and watched us drive away.
Connect with the Locals
At the same time, Route 66 thrives on stories, and connecting with the locals is one of the best ways to hear them. They’re often eager to share insights, offering tidbits about the highway’s heyday, pointing out hidden gems, or talking about ongoing preservation efforts. If you’re lucky, you might chat with someone who knows the real-life inspirations behind the characters in the Pixar movie “Cars” or hear insider details about an upcoming roadside attraction that’s bound to draw attention.
A Route 66 Road Trip Takes Stamina
Driving 2,448 miles isn’t for the faint of heart. It takes the endurance of an ultra marathoner to drive the full route, especially if you’re sticking to the original sections. Even as a road trip enthusiast (whose father did all of the driving), I found myself exhausted toward the end. If you can’t take three weeks for the full journey, consider breaking it into smaller trips over time.
It’s a Fantastic Multi-Generational Adventure
Route 66 may conjure images of baby boomer kids packed into a station wagon taking a carefree family vacation to the Grand Canyon or Disneyland. And, if you can drive the Mother Road with someone who remembers life in America before the Interstate Highway System, it will definitely add to your experience.
While driving 2,448 miles through eight states, my dad shared vivid memories of the evolution of America’s highways. Although it wasn’t part of Route 66, he recalled how the first stretch of Eisenhower’s interstate highway project that opened along I-70 just west of Topeka when he was in elementary school started transforming the country as it spread like a concrete web, reshaping small towns and revolutionizing road travel.
He also reminisced about his first time staying at a Howard Johnson’s, marveling at 24-hour room service, standardized menus, and the novelty of a motel swimming pool. These stories 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 Likely Want to Drive Route 66 Again
Although it was decommissioned as a road more than four decades ago, Route 66 continues to evolve. Each year, abandoned buildings further decay while restoration efforts breathe new life into others. As the centennial approaches, 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
Whether you tackle the entire route or explore a single section, be sure to take your time, respect its history, and savor the experiences of your Route 66 road trip. After all, you might find yourself planning a second trip to get your kicks before you’ve even unpacked!
Have You Driven Route 66?
What did you like most? 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.
