Last September, I crossed a dream trip 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 trip. For most Americans, carving out three weeks of vacation to make the end-to-end journey is nearly impossible, 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 route 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.
Take a map or an app
As a ghost highway, Route 66 isn’t always easy to follow. You can’t just ask Google Maps for directions along a road that was decommissioned in 1985. You’ll need tools to help you navigate like a Route 66 app, guidebook or old-school paper maps. I used the Route 66 Navigation app paired with the “Here It Is! Route 66 Map Series” by Jim Ross and Jerry McClanahan. I also recommend McClanahan’s “EZ66 Guide for Travelers.”
Route 66 is constantly changing — especially with the highway’s centennial approaching in 2026 — and no single source is perfect. For the best experience and to ensure you don’t miss a thing, I recommend consulting at least two tools or guides.
Drive from sunrise to sunset
The magic of Route 66 unfolds between sunrise and sunset with ever-changing landscapes, quirky roadside attractions and crumbling relics of the past whispering stories of the road’s golden age. Driving during daylight not only helps you take it all in but also makes spotting these hidden gems easier.
In its heyday, Route 66 was a neon wonderland, with glowing signs lighting up the night sky. Today, many of those iconic signs have had their tubing removed. While they no longer dazzle after dark, their faded charm still captivates in natural light, making daytime travel all the more rewarding.
Don’t rush through the Midwest
With some of the Route’s most scenic spots and iconic landmarks in the West, it’s easy to understand why many travelers hit the gas pedal in Chicago like a NASCAR driver with a green flag. But Route 66’s midwestern stretch deserves your time. From charming small towns to restored roadside icons, this region offers a richness that’s easy to overlook in the race to reach Arizona or California.
Plus, driving 200 miles in Illinois takes much longer than 200 miles in New Mexico. Most of the original route through Illinois has been preserved, and the state has poured resources into historic Route 66 signs, informational way stations and roadside attractions. You could easily spend four or five days in the Land of Lincoln, savoring the history and character at each stop, and still wish for more time.
In New Mexico, however, much of the route has been swallowed by I-40 with a lot more distance between Route 66 stops. At 75 mph, staring at the back of a semi, 200 miles disappear in a little less than three hours.
Respect the signs — and the locals
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 people or animals. 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. Expect the unexpected and tread lightly.
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.
The trip requires endurance
Driving 2,448 miles isn’t for the faint of heart. It takes stamina to traverse the 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 perfect 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 experience it with someone who remembers life in America before the Interstate Highway System, it will 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 crumble a little more, 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, when exploring Route 66, take your time, respect its history and savor the experience. After all, you might find yourself planning a second trip to get your kicks before you’ve even unpacked.
Sage Scott was bitten by the travel bug as a preschooler when her family moved abroad for the first time. Now settled in America’s Heartland, Sage is a travel writer, world wanderer and photographer whose favorite color is golden hour. Follow her adventures at Everyday Wanderer.