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People often ask what it’s really like to spend eight days driving the entire length of Route 66 with another travel writer. Three days in, I can honestly say… it’s entertaining.
People keep asking how this crazy adventure even came about. Ironically, it all started with a cookbook.
Both Cindy Ladage of Traveling Adventures of a Farm Girl and I were sent copies of the Route 66 Cookbook to review. Somewhere between talking about recipes, roadside diners, and all the iconic stops featured in its pages, one of us jokingly said, “Well… I guess we’ll just have to drive the whole thing.”
Instead of laughing and moving on like reasonable people, we kept talking.
Before long, that joke turned into an actual plan. We realized that by pooling our contacts, tourism partners, media experience, and Route 66 assignments, we could create something much bigger than either of us could have done alone. What started as a conversation over a cookbook became an eight-day, end-to-end adventure down America’s Mother Road, capturing stories for television, magazines, social media, and, most importantly, ourselves.
Sometimes the best adventures don’t begin with a carefully crafted business plan. Sometimes they begin with a cookbook… and two women who don’t know when to stop saying, “Wouldn’t it be fun if…”
So we did. We had a spreadsheet, dug in for “must see” stops, and then started working our connections.
As a member of SATW, I used one of my membership perks through Auto Europe to book our rental car for this epic road trip. Unfortunately, neither I nor Cindy caught one tiny little detail before arriving at O’Hare.
Our reservation was for the following week.
Oops.
The folks at the Avis counter kindly informed us that not only was our reservation unusable, but there wasn’t a rental car available anywhere at O’Hare. Not from Avis. Not from anyone. Well… that’s not exactly how you want to kick off a 2,400-mile road trip.
Thankfully, I reached a wonderful representative at Auto Europe who did everything he could to help. The best solution? Move our reservation to Monday and have us pick up the replacement car in Oklahoma City. Perfect. Except for one minor detail.
We were standing in Chicago on Saturday. And we still had Illinois and Missouri to cover before Oklahoma.
A frantic Priceline search led us to a rental available at Midway Airport, followed by an Uber ride across town. The rental center was packed, tempers were running high, and several customers ahead of us were making sure everyone knew how unhappy they were.
Meanwhile, Cindy and I did something radical: We smiled. We chatted with the staff. We treated them like human beings. Imagine that. Funny enough, our kindness seemed to pay off. We were in a car and headed down the road before several of the drama queens and kings who had been loudly demanding service.
It’s amazing how far a little grace still goes.
Honestly, getting a major travel disaster out of the way in the first hour of our first road trip together probably wasn’t the worst thing that could have happened. We stayed calm, solved the problem, laughed through the chaos, and only started our adventure about three hours late.
I’d call that a win.
Then came our first gas stop. Apparently, rental cars no longer come with owner’s manuals.
After spending a solid ten minutes searching for the fuel door release, pushing every button we could find, and questioning our combined intelligence, Cindy accidentally leaned against the side of the vehicle.
Pop.
The fuel door opened. The gentleman at the pump across from us laughed. We laughed. Somewhere, a “How many blondes does it take to pump gas?” joke wrote itself.
That faithful little rental carried us all the way to Oklahoma City, where we returned it to Budget and walked next door to Avis to pick up the car Auto Europe had rebooked for us.
As an apology for the mix-up, we’d been upgraded to a luxury SUV.
Fancy.
Until we couldn’t find the key. We searched the center console, the door pockets, the little recesses in the handles, flipped down both visors, and even managed to confuse ourselves trying to open the glove box.
Finally, we admitted defeat and drove to the exit gate. The attendant simply pointed through the windshield. The key was sitting on the dashboard.
Cue another blonde joke. (sigh)
To make us feel better, he admitted he couldn’t figure out how to open the glove box either.
I drove us to our first restaurant, where I celebrated surviving the day’s adventures with a well-earned glass of wine. Since Cindy skipped the wine, she took over driving to our historic Route 66 motel.
Somewhere along the drive, inspiration struck. Or maybe it was the Chardonnay, because I suddenly figured out how to open the glove box. Apparently, all I needed was a glass of wine to improve my automotive engineering skills.
We were only three days into an eight-day Route 66 adventure. Five days remained. At this point, we were almost afraid to ask what the Mother Road had planned for us next.
Almost.
Of course, the rental car adventures were only part of the story.
In just six days, we’ve slept in historic Route 66 motels, spent the night inside a beautifully restored fire station museum, and enjoyed the elegance of La Fonda in Santa Fe. We’ve hunted for kitschy roadside souvenirs, stood where Pixar found inspiration for Cars, eaten our way through iconic Route 66 restaurants, explored Indigenous history, wandered museums that left us in tears, and even visited a town where the donkeys have completely taken over.
As different as those experiences have been, they’ve all shared one thing in common: The people.
Everywhere we’ve gone, we’ve met people with hearts of gold. People who were genuinely excited to share their hometowns. People who pointed us toward hidden gems, told family stories, prayed over our journey, wished us safe travels, and repeatedly reminded us…
“Stay hydrated.”
So we did. Lots and lots of water. Which led us to discover one unexpected fact about New Mexico. Apparently, the state isn’t especially interested in people having to pee.
If you’ve driven the historic stretch of Route 66, you know exactly what I’m talking about.
Tucumcari? Nothing. Not a public restroom. Not even a friendly shop willing to let two desperate travelers borrow one. The Circle K politely said no. Every roadside sign promised gas, food, and drinks—but somehow managed to leave out the tiny detail that there wasn’t a restroom attached.
Even the trees weren’t big enough to provide a little dignity.
By then, it had become our running joke. “Maybe the next stop…” “Nope.” “Surely this one…”
“Nope.”
Coming from Texas, it felt like we drove forever before finally reaching the promised land. A Love’s Travel Stop in Santa Rosa. Never in my life have I been so happy to see that bright yellow sign with the heart.
It Helps to Have the Right Person in the Passenger Seat
I learned pretty quickly that Cindy was exactly the right person to have beside me when things went sideways.
Every morning before we pulled out, we prayed for our families, for safe travels, and for whatever the road had in store for us that day. Then we went out and dealt with whatever it actually had in store—which, apparently, included missing rental cars, mysterious gas caps, invisible keys, and eventually a desperate search for a bathroom.
We could laugh when things went wrong, adjust the plan without blaming each other, and somehow still have plenty to talk about after spending day after day together in the car.
There are people you can have lunch with, people you can travel with, and people you can discover you have no rental car with at O’Hare and still like three hours later. Cindy, thankfully, turned out to be all three.
Travel has a funny way of reminding you what really matters.
Sure, you’ll remember the famous landmarks. You’ll remember the pie, the motels, the museums, the quirky roadside attractions, and the beautiful scenery. But years from now, I suspect what Cindy and I will laugh about the most are the rental car that wasn’t, the gas cap that defeated two blondes, the invisible car key, the glove box that apparently required wine to operate… and our triumphant arrival at Love’s after what felt like the longest search for a restroom in Route 66 history.
The Best Road Trips Aren’t Perfect
They’re filled with detours, unexpected kindness, inside jokes, and stories you could never have planned. Route 66 gave us plenty of all four.
We set out to drive the Mother Road from beginning to end, armed with a spreadsheet, assignments, reservations, and a pretty good idea of how the trip was supposed to go. Somewhere along the way, the plan became far less important than the story we were actually living.
And maybe that’s the real trick to a great road trip: plan enough to get yourself out the door, then leave enough room for the road to surprise you.
Just don’t pass up a clean restroom when you find one.
FAQs About Driving Route 66
How long does it take to drive Route 66 from Chicago to Santa Monica?
You can technically drive Route 66 much faster, but if you want time for historic sites, diners, museums, roadside attractions, and small towns, give yourself as much time as possible. We tackled the entire route in eight days, which made for an exciting but very packed itinerary.
How long is Route 66?
Historic Route 66 stretches roughly 2,400 miles from Chicago, Illinois, to Santa Monica, California. The exact mileage varies depending on which historic alignments and detours you follow.
Do you need a rental car to drive Route 66?
If you’re flying into Chicago and home from California, a one-way rental car can be one of the easiest options. Double-check your reservation dates, pickup location, drop-off location, and one-way policies before you arrive. I learned the importance of that first one the hard way when we arrived at O’Hare and discovered our rental reservation was for the following week. Pasted markdown
Should I reserve a rental car for Route 66 in advance?
Absolutely. Availability can be limited, especially for one-way rentals. Our mistake left us scrambling from O’Hare to Midway Airport just to find a vehicle that could get us started. Pasted markdown
Are there plenty of restrooms along Route 66?
Not necessarily. Some historic stretches have long distances between reliable public restrooms. Tucumcari, New Mexico, proved particularly challenging for us, and we eventually found a restroom at a Love’s Travel Stop in Santa Rosa. My new Route 66 rule is simple: if you see a clean restroom, use it. Pasted markdown
What should I plan before driving Route 66?
Book your rental car and lodging, identify your highest-priority stops, and research where fuel and other services may be limited. But don’t schedule every minute. Some of our best experiences came from unexpected stops, conversations, detours, and recommendations from people we met along the way.
Is Route 66 still worth driving?
Yes, especially if you enjoy American history, quirky roadside attractions, historic motels, diners, small towns, and meeting the people who keep the Mother Road alive. The landmarks are memorable, but some of our favorite stories came from everything that went wrong between them. Pasted markdown
