GETTING OUR KICKS ON ROUTE 66

PART ONE

Follow us all the way to Santa Monica, CA, in the next three TravelWorld International issues!

Since the day I first got my license, I’ve dreamed of driving on Route 66. With 2026 marking the famed highway’s 100th anniversary, it was time for the rubber to hit the road. I had planned to take the trip alone, but never one to miss a good time, Terri decided to join me after I repeatedly assured her husband that—at some point—we would return.

Spanning 2,400 miles from Chicago to Santa Monica, CA, this “Main Street of America” was officially established in 1926. From the 1920s to the 1950s, the Mother Road was in its heyday, with roadside businesses popping up all along the route to service adventurous drivers. Unfortunately, the development of the interstate highway system led to the downfall of the original route, though its centennial year is once again attracting road trippers to this All-American journey—and the weird and wonderful roadside attractions that still stand along the way.   

Day 1: Chicago 

We started in Chicago, where Route 66 officially begins, and spent our first day exploring the Windy City. Our first stop was lunch at the Elephant & Castle, an English pub, which has absolutely nothing to do with the route, but we needed to officially toast the trip before we hit the road. We wandered through Millennium Park, made faces in the reflective art piece, “The Bean,” and rode around the Chicago Loop on the El, peering into office windows. We spent the night in luxury at Terri’s brother’s apartment, which was the last time we would experience any form of luxury for the foreseeable future.  

Day 2: Chicago to Bloomington, Illinois 

After a good night’s sleep, we began our journey at the famed Lou Mitchell’s Café, where we sat with other Route 66ers (we forgot to make matching t-shirts) before hitting the road. Lou Mitchell’s has been a Chicago institution since 1923 and is a popular starting spot for in-the-know Route 66 fans—which is us, of course. 

Terri (perusing her book): This EZ66 Guide for
Travelers doesn’t just give us directions; it lists
attractions along the way. So, in addition to
directing every turn, I’ll be telling you every stop
for photos.
Vanessa: I was not aware that Route 66 goes
through Hell on the way to Santa Monica.

We are both mural junkies and had to stop for every mural and every Route 66 giant Muffler Man-type statue in our path. Our first sighting was a barbecue joint with a Route 66 mural displaying aliens and a cigar-smoking man on top of the building. Next came White Fence Farms, where large cow statues distracted us from a very angry nesting goose, which was nestled in a large barrel lined with “Do Not Disturb” signs in front of the restaurant. An odd mix for sure, but this was a popular stop on Route 66 in the early 1920s and still attracts diners today.  

Next, we hit Route 66 Park in Joliet, IL where Blues Brothers statues dance on the roof of an ice cream stand. The real attraction, however, was across the street: Dick’s on 66—an old garage with vintage cars, a tow truck and car on the roof, and the name DICK’S spelled out in license plates. The funky scene also included a small section of the original Route 66 roadway crafted from bricks, where of course, we had to stop for a selfie. 

Day 3: Bloomington, IL to Cuba, Missouri 

Why they have an Atlanta in Illinois and a Cuba in Missouri is beyond us, but it turns out, those cities were two of our favorite stops. We liked Bloomington so much, in fact, that we drove in circles for an hour—thanks to Terri’s navigational expertise.

Terri: Why do you keep turning?
I didn’t say to turn!
Vanessa: You absolutely did!
Terri: I was reading the map to myself.
I wasn’t talking to you.
Vanessa: I’m supposed to know that? Like
you’re talking to me for 500 miles, and now
you’re not? But you’re still talking? Who does
that?

Terri Pleads Her Case: When you’re on the road with a friend for several weeks, you need to learn how they take instruction—especially as the navigator. I talk a lot, and that includes reading aloud the upcoming set of directions from the guidebook. This turned out to be overwhelming for my driver, who rarely takes instructions, but somehow decided that she was going to listen to those. After three or four or 100 wrong turns (and SO many swear words), we resolved the problem by me saying “Vanessa” before giving her any instructions. Then I started saying her name in different accents. As you can imagine, she absolutely LOVED that. 

Arriving in Atlanta, IL, we noticed a decided lack of traffic; we were actually the only car around. It was a far cry from the Atlanta we know, and that was fine with us. The town is home to the American Giants Museum, which you can’t miss because there is a massive Texaco serviceman and oversized Alfred E. Neuman statue outside. (It is also located directly across from Chubby’s Bar and Grill, whose mural promotes Reisch beer—”To Give You Health and Strength”). 

Inside the museum, we found two lovely docents who shared fascinating information on the history of these roadside giants, as well as a collection of nostalgic statues, including Big Boy, Mama Burger, Baby Burger, and the Texaco Tiger, among others. We were smitten.  

Heading out of town, we spotted a Bunyon Giant holding a hot dog, which used to be in Cicero, IL, on a hot dog stand until an ordinance said it had to come down, and a giant Pie Lady proudly standing in front of the local diner. Surreal doesn’t begin to explain it. 

Crossing a bridge into St. Louis, MO, we decided to take a detour to visit Gateway Arch National Park and take a ride to the top of the 630-foot-high, 630-foot-wide arch, which is a modern-day architectural miracle. However, the “pod” you ride in is tiny and feels akin to sitting in a hot, sticky, damp clothes dryer, which Vanessa loved, since she is semi-claustrophobic.  

Terri: Just relax! You’ll love the
stunning views at the top; you
can see 30 miles in each direction
on a clear day.
Vanessa: I hope so, because I’ll be
living there until there’s another
way to get back down.

After much persuasion, we made it back to ground level and took off for Cuba, MO, and the Wagon Wheel Motel, where the owner had left the key to our cottage under the plant outside the office. Some trusting people live in Cuba, MO. We finished the evening with dinner at the restaurant Frisco, where a singing server shared her goal of becoming president one day. We signed up to become her campaign managers and called it a night. 

Follow us all the way to Santa Monica, CA, in the next three TravelWorld International issues!