Backwards on the Mother Road: Our Route 66 Centennial Journey Begins

So, Grandpa, is there any truth to that old song — the one that tells you to get your kicks on Route 66? We spent the next two weeks finding out. We're traveling all 2,500 miles of the Mother Road for its historic 100th birthday, and true to form, we're doing it backwards — Santa Monica to Chicago. When Grandpa Scott was young, he used to play his Beatles records backwards just to see what he'd find. So that's us: your backwards grandpas, and this is the story of our first day on the road.

https://youtu.be/8eKQwUcx_tM?si=1zwEGP3JCTyL2NNx

A Reverse Journey Begins

Our journey started on the famous pier in Santa Monica, where we picked up our official Route 66 passport from a lovely woman named Michelle. From here on out, we are going to stop at famous, and some unknown spots along Route 66 and let you know how many kicks we rate them.

The Original Golden Arches

Our first real stop was one for the history books: the very first McDonald's site, right here on Route 66 in San Bernardino, California, founded in 1951. They don't serve fries here anymore, but they do have a museum packed with historic merchandise, and it draws visitors from all over the world — Germany, Japan, Russia, China, you name it.

Grandpa Scott has always had a thing for collecting — at one point he owned over 200 cookie jars, though never one shaped like a hamburger. This stop earned a half-kick on our Route 66 Kicks Scale — docked a little only because, well, no fries.

An Enchanted Bottle Forest

Next up was one of the stops we'd most looked forward to: Elmer's Bottle Tree Ranch, over 200 trees built from bottles collected from all over the planet. It's a wonderful, playful piece of American folk art, free to visit, made purely as a labor of love. We even brought a bottle of our own — a Cabernet, of course — to leave behind as a donation to the project.

Elmer's Bottle Tree Ranch earned Super Kicks from us — it really is like walking through an enchanted forest.

The Iconic Baghdad Cafe

From there we rolled into Newberry Springs for the iconic Baghdad Cafe, made famous by the 1988 film of the same name. It started life as the Sidewinder Cafe, and the name has flipped back and forth between Sidewinder and Baghdad over the decades — Andrea Pruett brought back the Baghdad name for good when she bought it in 1991. About 85% of visitors here are French, even though the film was made by a German producer. Every inch of the walls is covered in photos and mementos from travelers who've passed through, including — if you look closely — a dollar bill of ours.

We met the delightful Miriam here, and that sealed it: this stop got 10 kicks out of us, no question.

The Silence of Roy's Motel

Roy's Motel and Cafe, first opened in 1926, is one of those Route 66 landmarks that captures both the romance and the loss along the Mother Road. The highways eventually pulled the lifeblood out of places like this, and today it sits mostly vacant — just the iconic sign, a few derelict rooms, and a small cafe with a gift shop full of Route 66 memorabilia. Given how much of the original site is gone, we gave it three kicks, with real respect for its place in the road's history on this, its 100th birthday.

The Wild Donkeys of Oatman

The historic mining town of Oatman, Arizona, is famous for its wild burros — descendants of the original mining donkeys, now free to roam the streets and greet (gently!) every visitor. Local legend says Clark Gable and Carole Lombard spent part of their honeymoon at the Oatman Hotel. There's no hard evidence, but it's a good story and we're happy to go along with it.

Oatman is a real piece of Americana — a little worn around the edges, but full of character. We gave it five kicks.

Milkshakes in Kingman

Kingman has been an important Santa Fe Railroad stop for generations, and it's still an active railway hub today — though, the Kingman Railroad Museum was closed when we arrived, just like it apparently is for every other Route 66 vlogger who's ever tried to visit. We consoled ourselves with classic chocolate shakes at Mr. D's, a 1950s diner packed with vintage cars, and a stop at Hackberry General Store — one of the real-life inspirations for Radiator Springs in the Cars movies, complete with an Elvis presence around every corner and dollar bills pinned to the ceiling.

Kingman earned three kicks (great milkshakes, closed museum), and Hackberry General Store two kicks of its own — cold water, live music, and plenty to look at.

The Snow Cap Drive-In

In Seligman, Arizona, we stopped at the famous Delgadillo's Snow Cap Drive-In. Angel Delgadillo and his family led the charge to get Route 66 officially designated as a National Historic Route, and this place has become a pilgrimage site because of it — we heard half a dozen languages in line, all travelers who'd found this little hamburger stand through YouTube and social media. Grandpa Scott had the smiley-faced chicken nuggets, Grandpa Bobby had a hot dog, and both of us agreed: 10 kicks, easily, for the food and for everything the Delgadillo family has done to keep Route 66 alive.

On to Flagstaff

Day two started with the scenery turning from desert to mountain greenery as we climbed the road up to Flagstaff, home to Northern Arizona University and our first muffler man sighting — a 25-foot fiberglass giant known here as Louis the Lumberjack, donated to NAU in 1979. Fun fact: Route 66 is also known as the Will Rogers Highway, named in honor of the road's most famous champion after his death.

We checked out the Hotel Monte Vista, built in 1927 and once host to Hollywood names like Jane Russell, Spencer Tracy, and Humphrey Bogart — and reportedly one of the most haunted hotels on the entire route. There's also a great local legend that MGM's Louis B. Mayer nearly built his movie studio in Flagstaff, until a snowstorm on the day he arrived sent him on to California instead. Imagine Flagstaff as Hollywood!

Lunch was a happy surprise: a proper Cornish pasty shop, chips and all, tucked into Flagstaff. Between the history, the food, and the people, Flagstaff earned seven kicks from both of us.

Don't Forget Winona (and a Song That Started It All)

In 1946, songwriter Bobby Troup and his wife were driving west when he decided to write a song about this road. He needed a town name to rhyme with Flagstaff, Arizona — so "don't forget Winona" made it into the lyrics. We didn't forget it either, though when we got there, we found there wasn't much town left to see. We followed that up with stops at Twin Arrows, where only one of the original two telephone-pole arrows still stands (its twin fell in 2022 and hasn't yet been restored), and Two Guns, where we found only unverified ruins of what may once have been a trading post rivalry with Twin Arrows. Between the three, we landed on a modest one-to-two kicks — equal parts iconic and genuinely a little melancholy to see what's been lost.

Standing on a Corner in Winslow

Standin' on the Corner Park in Winslow, Arizona pays tribute to the Eagles' 1972 hit "Take It Easy," written by Jackson Browne and Glenn Frey. As the story goes, Browne started the song while stranded in Flagstaff but couldn't make the words fit — so Winslow made it into the lyrics instead, and the town has embraced it ever since. Expect non-stop Eagles music wherever you wander here.

The Jackrabbit Trading Post

The Jackrabbit Trading Post, established in 1949, is one of the most recognizable landmarks on Route 66, thanks to a marketing campaign of mile-marker signs ("30 Miles... 20 Miles... Here It Is!") that made the black jackrabbit statue famous long before you ever arrive. Owner James Taylor — not the singer — reportedly drove around with a jackrabbit statue in his convertible, and the name stuck for good.

A Night at the Wigwam Motel

We ended this stretch of our trip in Holbrook, Arizona staying at the Wigwam Motel — one of only three of the original wigwam motels left standing from the 1950s. Each unit comes with a classic car parked out front (ours was a beautiful Chevy Impala), a Formica countertop desk, a cozy little seating area, and — thankfully — air conditioning that was not part of the original 1950s build.

It had been a long, wonderful first day on the road. Tomorrow, we cross into New Mexico — one of our favorite states — but for now, it was time for a little shut-eye.

What's Next

This is only the beginning of our 2,500-mile trip down the Mother Road, and we can't wait to show you what New Mexico, Texas, Oklahoma, and the rest of the route have in store as we make our way — backwards, of course — all the way to Chicago.

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Love Grandpa Bobby & Grandpa Scott