Route 66 Part 3: Our Last Kicks from Missouri to Chicago
There is a particular kind of quiet in a 1929 motor court at six in the morning — no highway hum, no elevator ding, just birds and the smell of coffee. That is how the last leg of our Route 66 trip began. We had already come all the way from the Santa Monica Pier, driving the Mother Road backwards the way we do most things, and there were only a few hundred miles of it left before Chicago.
Here is how the last of it went — and what we gave each stop in kicks.
The Oldest Motor Court Still Standing on Route 66
We started day six in Springfield, Missouri, at the Rockwood Motor Court — built in 1929 and recognized as the oldest operating motor court on the whole of Route 66. Phyllis and Tim, who bought the place and brought it back, have restored every cabin with real love, and each room carries its own theme.
We picked the movie room, and it was wonderful. There is a little seating nook where the original kitchenette used to be — they decided travelers today would rather have somewhere to sit than somewhere to cook. And then there is the bathroom: black and white, absolutely pristine, what we would call a tuxedo bathroom, carrying the movie theme right through.
This is one of the most popular places to stay anywhere along the road, so book well ahead. We will put a link to their website below.
Nine kicks. Beautifully restored — and they left us snacks.
Where the Road Got Its Number — and a Sign That Was Too Tall
Springfield calls itself the birthplace of Route 66, and it has a fair claim. In 1926 the telegram that proposed the number 66 for the new national highway went out from here. The building is long gone, but the story stayed.
A few blocks away is one of our favorite pieces of roadside honesty on the entire trip. A local man named Sheldon “Red” Chaney opened a hamburger stand here in 1947 that is widely credited as America’s first drive-thru. He ordered himself a big T-shaped sign that was supposed to read GIANT HAMBURGER. When it arrived, it was too tall to clear the power lines. Red, being a practical man, simply had the bottom letters cut off — and Red’s Giant Hamburg was born.
The original restaurant served travelers until 1984 and was torn down in the nineties. The sign you see today is a faithful replica, standing at the Birthplace of Route 66 Roadside Park.
Six kicks — for the story alone.
Lebanon’s Neon, and a Missile in a Field
Down the road in Lebanon, Missouri, is the Munger Moss Motel, built in 1946 and one of the most photographed motels on the Mother Road. The motel itself is closed now, which we will admit stung a little. But the sign was saved: the City of Lebanon took ownership of it, maintains it, and lights it every
single night. We think that’s cool.
We rolled through in the morning, so we did not get to see it lit. We showed you all its daytime beauty instead, and we would tell any traveler with an evening to spare to swing back after dark.
Four kicks.
A little east of Lebanon we came across the site of the old Satellite Cafe. The cafe is gone, but one of the missiles is still standing out there in the open, and the only reason we found it was from a tip from a local. Pays to be friendly to the natives!. Two kicks for the memory.
The Tallest Rocking Chair on Route 66
How do you pass up the Fanning Outpost in Cuba, Missouri, home of the world-famous Route 66 Rocker — the tallest rocking chairs anywhere on the road? You do not. You pull
over.
Walmart has its greeter. Fanning has Oreo the cat, who greets you, more or less, on his own schedule. Inside you will find cold drinks, snacks, souvenirs, and — Grandpa Scott’s favorite — homemade fudge.
And somewhere in Missouri there is a roadside sign for a place called Uranus. It is not an iconic Route 66 sign by any stretch. It did give two grown grandpas a very good chuckle.
St. Louis: A Very Big Arch and One Very Big Mistake
Good morning from St. Louis, home of the Gateway Arch. We got there early, we stood underneath it, and boy is this puppy big.
We had every intention of riding to the top and filming it for you. And then we did a boo-boo — we forgot to make reservations. Traveling the way we were, never quite knowing where we would land each night, booking ahead was genuinely hard. But by the time the park opened, tickets for the elevators were completely sold out for the day. So, learn from us: make your Gateway Arch reservations in advance.
It is still a beautiful thing to stand under. Designed by Eero Saarinen — one of Grandpa Bobby’s favorite architects — and finished in the 1960s, it’s 630 feet tall and 630 feet wide, which makes it taller than the Space Needle in Seattle.
We then walked down from the Arch to the Mississippi River, and this was a first. Scott is one of nine children, and the only one in the family who had never laid eyes on the Mississippi River — until his seventy-seventh year.
Seven kicks — even from the ground.
Concretes at Ted Drewes
We had a goal of eating our way across Route 66, and Ted Drewes Frozen Custard on Chippewa Street is one of the great required stops. The Drewes family has been making custard in St. Louis since 1929, and this stand has sat right on the Mother Road since 1941.
Their shakes are so thick they refuse to call them shakes. They are called Concretes — and they encourage you to hold them upside down to prove the custard will not budge. We did not test this in the car. We are not brave, nor did we relish a cleanup on aisle nine! We simply enjoyed them: lemon for Grandpa Scott, chocolate for Grandpa Bobby.
Eight kicks.
Crossing Into Illinois
Just north of St. Louis, near Chouteau Island, is the old Chain of Rocks Bridge — built in 1929, with a famous twenty-two-degree bend right in the middle of it. From 1936 until the interstate took over in the late sixties, this was how Route 66 crossed the Mississippi. Cars have not driven the bridge in decades; today it belongs to walkers and cyclists. We love a historic bridge, so three kicks from us.
Further down the road we encountered the age-old question: is it catsup or ketchup? Neither, really. The giant bottle is actually a water tower. Four kicks, and on we went.
Drive-Ins, Corn Dogs, and the Oldest Cafe on the Road
The Sky View Drive-In in Litchfield, Illinois, opened along Route 66 in 1950 and has been running ever since. Grandpa Bobby made us stop, because drive-ins were the whole of his childhood and they are pure Americana.
Grandpa Scott remembered his first one: freshly minted learner’s permit, the family car borrowed, and two extra friends smuggled in the trunk. Very common at the time. Grandpas Bobby remembered being on the other end of it — little kids sent to the drive-in in their pajamas because it was always a double feature, falling asleep in the back seat while the grown-ups sat up front with a paper bag of homemade popcorn. Seven kicks from both of us.
A little further along is the Ariston Cafe, founded in 1924 and settled into its current building in Litchfield in 1935. It is the oldest continuously operating restaurant on Route 66 and it is on the National Register of Historic Places. It is also closed on Mondays, which is exactly the day we arrived. Oh well, you can’t win them all! Next time.
We made up for it in Springfield, Illinois, at the Cozy Dog Drive In, which claims to have introduced the corn dog back in the 1940s. Your grandpas felt obligated to do our due diligence. The verdict: a really crisp corn taste on the outside, and — this is the part that matters — the batter does not fall away from the hot dog. It sticks right to it. The dog inside was fresh and tasty, and the people working there were as nice as anyone we met all trip.
Eight kicks each, and we agreed on it — which, for us, is news. Love always wins. Even in corn dogs.
Seventeen Years at the Lincoln Home
Also in Springfield, Illinois, is the home where Abraham and Mary Lincoln lived for seventeen years — the longest Lincoln ever lived anywhere before he left for the White House. While it is not a typical Route 66 stop, we think it is an important one.
Walking through those rooms, you cannot help but imagine the life inside them: how they entertained, where they sat. The colors and bold patterns look loud to modern eyes, but that was high Victorian style and very much in vogue. The bedrooms are all upstairs, and Mr. and Mrs. Lincoln had separate ones.
Yes, that really is horsehair upholstery. The enormous kitchen stove was state of the art when it was made, and we understand getting it there was quite an undertaking.
And you find yourself wondering. Did he stand in this house thinking about becoming president? Did he have any sense of the war he would carry? Did Mary Todd Lincoln imagine how completely her life was about to change?
Ten kicks — A moving experience and the highest single score we gave on the whole road.
The Last Muffler Man
In Wilmington, Illinois, stands the Gemini Giant — thirty feet of fiberglass astronaut holding a rocket, wearing a helmet that looks a great deal like a welding mask. He is the last muffler man of our trip, and he closes out our road.
He spent almost sixty years outside the Launching Pad Cafe. The cafe is gone now, and in late 2024 the Giant was restored and moved a few blocks down to South Island Park, where he has a new pedestal and is looked after properly — just in time for the centennial.
Eight kicks — For our final kicks along the road
Chicago, Where It All Started
Final day. We took the Mother Road all the way to its inception — the very beginning of Route 66, right there in Chicago. But there was one more thing.
We began this trip on the wharf in Santa Monica. So we finished it on the wharf at Navy Pier, where the commemorative start marker for Route 66’s hundredth birthday now stands. Pier to pier, backwards, the whole way. We could not have asked for a better ending.
The Final Leg, in Kicks
• Rockwood Motor Court, Springfield, MO — 9 kicks
• Red’s Giant Hamburg sign, Springfield, MO — 6 kicks
• Munger Moss Motel, Lebanon, MO — 4 kicks
• Satellite Cafe missile, east of Lebanon, MO — 2 kicks
• Gateway Arch, St. Louis, MO — 7 kicks
• Ted Drewes Frozen Custard, St. Louis, MO — 8 kicks
• Chain of Rocks Bridge, IL — 3 kicks
• Giant Catsup Bottle, IL — 4 kicks
• Sky View Drive-In, Litchfield, IL — 7 kicks
• Cozy Dog Drive In, Springfield, IL — 8 kicks
• Lincoln Home, Springfield, IL — 10 kicks
• Gemini Giant, Wilmington, IL — 8 kicks
So How Many Kicks Did We Get on Route 66?
We did it. Every mile from Santa Monica to Chicago.
When we sat down to sum it up, the places came first — the Bagdad Cafe out in the California desert, POPS in Oklahoma, the trestle at Santa Rosa, New Mexico, where Tom Joad sat and watched the trains go by in The Grapes of Wrath. Standing under that trestle, thinking about the book and the film and about what this road meant to families like ours, was one of the best moments of the trip. And here is something we did not expect: every site we visited, every place we parked, was free. Not a dollar
spent to stand in front of any of it.
But the places are not the answer. The people are.
Everywhere we went, in every small town, we were met with hospitality and friendliness — every single person. We wore our Two Gay Grandpas Travel shirts through all eight states on this road, and we did
not get one negative word. What we got instead was slaps on the back, hugs, and conversation. America is celebrating its two hundred and fiftieth birthday this year, and aside from the fireworks and the parades and the fairs, we cannot think of a better way to have commemorated it. Driving through all those small towns and meeting all those people left us certain of something: the vast majority of people in this country are gracious, kind and welcoming. In difficult times, that is worth remembering. It gives
us hope. That, for us, is the whole message of Route 66 — a road that ties this country together.
So, the final score for the entire trip? There is only one right answer.
2,448 kicks — one for every mile of Route 66, so that no one gets left out!
Have you driven any part of the Mother Road — or is it still on your list? Tell us in the comments!
Watch the full final episode of our Route 66 Centennial series on YouTube, where you can see every one of these stops for yourself — and catch up on Part 1 and Part 2 if you are joining us late.
Follow along on Instagram, Facebook and TikTok for more from the road, and subscribe so you do not miss where these two grandpas turn up next.
Travel Your Heart
Grandpa Bobby &
Grandpa Scott
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