An Illinois Road Trip Adventure: Route 66

Start where the Mother Road begins and explore Route 66 in Illinois.

In July, 2020, I drove nearly 1800 miles in four and a half days researching scenic drives for “Midwest Road Trip Adventures,” an anthology from experts in the Midwest Travel Network. This is my account of the experience.

I pulled out of our driveway at 6:18 am on Tuesday, June 30. An hour later I was at the Chicago Cultural Center.

I wasn’t quite at the beginning of Route 66, yet. The official start of my journey would be the intersection of Adams and Michigan, but when I approached the turn was blocked. A machine was breaking up old pavement and tossing it through a chute into a dump truck in front of it, both tailed by a machine that rolled fresh asphalt over the top. There was no way I could cross anytime soon.

My trip began with a literal road block.

“Is this a bad omen?” I wondered. Then stopped myself. That’s not me. I’m not doom and gloom. This happened for a reason.

And so it had. I found a parking spot on Wabash Avenue and walked around the corner. Found the “Historic Illinois Route 66” sign covered with stickers.

The beginning of Route 66 in Illinois is at Adams and Michigan in downtown Chicago

One of the stickers said “Live a Great Story.” I turned around to walk back to Sally the Santa Fe (for Sally Ride, because I would be flying through these byways) and came across another sign. It stood in the shadow of a tree and the L, proclaiming “Illinois US 66 – Historic Route Begins.”

Stickers in multiple languages covered the back side of this sign. There was even a NASA sticker – is that where I decided to name her Sally?

It was a proud sign. A tall sign. It was my sign, that yes, there would be road blocks. I’d make wrong turns. I’d deal with frustration. But, I would find my way. I would live a great story.

Illinois Route 66 sign with the L tracks in the background
This sign is at Wabash and Adams, a block west of the “official” start of Route 66 in Illinois

As I walked back to Sally, the SUV I’d rented for this crazy excursion, the thing I dreaded most happened:

I had to use the bathroom.

It was 7:40 am. Nothing was open since it was early and the city was still shut down. I drove west on Adams, picked up Ogden, following the Route 66 signs.

I would quickly learn, and this fact remained consistent on all four byways I drove, that while the routes are fairly well marked, there’s seldom advance warning before a turn. (I did a lot of U-turns.)

I couldn’t plug the drive into Waze or Google maps. This hadn’t been an official route since 1985. I had to rely on my state to show me the way.

Somewhere near Berwyn I followed a sign and to my left was a Jewel-Osco.  Aha!

Grocery stores had been on my potty break potential list. I went inside, did my business, washed my hands, got back into Sally. Wiped my hands, my purse, the door handle, the keys, anything I’d touched with a wipe, then liberally applied sanitizer. Oh, what was that smell?! Tequila. The sanitizer smelled like tequila.

Finding that bathroom was a relief, in more than one way. I knew I’d been anxious about relieving my bladder; I didn’t realize how anxious. I wouldn’t be driving interstates, so rest areas weren’t an option.

Gas stations, I knew from previous experience, could be a bit sketchy. Grocery stores, with their emphasis on selling things people put in their mouths, tend to have cleaner facilities. (Tend to. We both know there are grocery store bathrooms that seem like a piece of fruit somebody forgot in the back of the crisper.)

Now. Now I was on my way. Let the adventure begin!

Jake and Elwood at Route 66 Park in Joliet Illinois

Jerry McClanahan’s Easy Guide to Route 66 sat on top of my mini-cooler in the passenger seat. Mr. TLT and I had picked up this turn-by-turn bible when we drove the Mother Road in 2011. We didn’t get it until we were in Missouri, though, so we missed several stops in Illinois. Several. For instance, the Vegas-like sign in McCook, and Route 66 Park in Joliet.

Announced by an ice cream shack topped with Jake and Elwood Blues, it should have been hard to miss. It wasn’t new, either: I could barely read the several wayside exhibits because their surfaces were warped and peeling and the text and images had faded.

I know I would have remembered the old gas pump or the statue of a thin, reclining man atop a mosaic column of undersea life. We must not have driven that way.

Old gas pump at Route 66 park in Joliet
Sculpture in Route 66 Park in Joliet

I spent a lot of time at that park. I think I was getting acclimated to the idea of driving Route 66 in Illinois in one day, then driving the National Road, then Ohio River Scenic Byway, then the Great River Road.

I had made my decision to do this trip quickly. The deadline for the Midwest Road Trip Adventures anthology was approaching – the whole project seemed to drop in my lap in a blink. I considered doing my research after the July 4th weekend, but knew that would give me all of about five days to do the actual writing. I decided on Monday morning, rented a vehicle by noon, picked it up at 5 pm, and thirteen hours and eighteen minutes later I was driving.

It’s no wonder Jim thinks I’m crazy.

I took pictures of every faded sign, of the gas pump, of the fountain. I walked a short path to an overlook to see the prison from the Blues Brothers. The overgrowth was so thick I could barely see the landmark. That’s how long that park had been there. 

I continued to follow Jerry’s turn-by-turn instructions, but I soon realized I didn’t need to because the route was marked. The book still helped because it pointed out things I should look for along the way, like Gemini Man in Pontiac and The Shop, a Coca-Cola-themed stop, in Gardner, population 1200.

The Gemini Giant on Route 66 in Illinois

I turned a corner in that town and pulled over to take a picture of a faded Route 66 sign on the road itself, moving out of the way as an older couple backed out of their driveway and stared at me. I couldn’t be the first person they’d seen stand in the middle of the road gawking at the painted emblem, but they sure looked at me like I was. Around the corner, in front of The Shop, fresher signs pointed the way around a bend, each sign advertising one of the eight states the route traverses. 

The Stop along Route 66

I saw a “Pritzker Sucks” sign. I was shocked and dismayed that someone saw fit to display this in their yard. It was my first hint that, even if I avoided people and the radio, politics would invade. 


In Dwight, Illinois, I pulled into the parking lot of Ambler’s Texaco. It was a surprisingly well-kept Texaco station. Surprising, because I was expecting merely a gas station on the corner, one like I’ve seen many times in many different places.

Instead, I found a full-on visitors center. Large parking lot. Family taking selfies in front of the big sign. Several interpretive markers. Old pumps restored. A thin man in a mask got out of his air conditioned red car and invited me to sign the guests’ log. He told me a bit about the history. He talked to a couple of women traveling this part of Route 66.

Wayside exhibit and billboard at the Dwight Illinois Visitor Center on Route 66
Ambler’s Texaco - Dwight Visitor Center on Route 66 Illinois

That station was the busiest attraction, besides Casey, that I’d see during the whole trip. He was a kind man who was proud of his town. When I asked if the renovation was sponsored by the state, he was affronted. “No!” he exclaimed. “This is all Dwight. All volunteers.”

He’d introduced himself as Jack, a volunteer, so maybe I should have guessed. Either way, he was proud. He told me other places I should see in his town. The windmill. The train station. The bank. It’s one of only two banks designed by Frank Lloyd Wright.

This was his home, and he wanted to show it off. He gave me clear and precise directions, including how to navigate the one-way streets around the town center.

Those are experiences you can’t have unless you get out of your car and say hello. The only down side was that I had a hard time hearing him through his mask and over the running vehicles. That’s OK. I’d rather he wore a mask to protect me, to protect those women, and to protect that young family.

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Even with his directions I still got a bit turned around. I was still trying to wrap my head around the whole experience. It was 12:30 or so by the time I left Dwight. I’d been traveling for over six hours and was still in the northeast part of the state. By that night I needed to be almost to St. Louis. Could I do it? Sure. I had to.

I was on the road for all of ten minutes when I pulled over at another refurbished gas station, this time in Odell. I listened to a recording about the history of the station. Previous travelers had plastered stickers, including my new mantra.

Live a great story.

That’s certainly what I was doing. Driving a road that symbolized, and still symbolizes, freedom.

The miles accumulated. I pulled over for every historical marker and wayside exhibit. I felt a jolt of glee every time I successfully found one of the points of interest Jerry mentioned in his book. My favorite was probably the stretch of bricks painted with bright yellow, threading through fields of corn and soybeans.

Original red brick on Route 66 in Illinois

It was supposed to thunderstorm all day, yet I managed to miss all but a few sprinkles. In one of the lonely stretches I pulled over to inspect the original pavement. Here I was, bent over to see what materials people of 1920 would have driven over. A couple slowed down to make sure I was alright. 

I drove. Past a giant Paul Bunyan cradling a hot dog. I missed turn after turn in Springfield, yet somehow found my way again. I passed the grave of a revolutionary soldier in Chatham. I followed the signs as they led me ever south and west towards the Mississippi.

As dusk descended I crossed a one-lane bridge over the Chain of Rocks Canal. There was a stoplight that turned green as I approached. I was alone. I crossed the bridge and the narrow road seemed like it hadn’t been driven in ages. I’d never disturbed so many birds. They hung out on the pavement like they were having a party. I reached the end and recognized the bridge. Jim and I had stopped there nine years ago on our Route 66 return trip. It had been dusk then, too.

Chain-o-Rocks Bridge on Choteau Island, the old Route 66 crossing from Illinois to Missouri

There were a couple of cars in the parking lot, but I didn’t see their occupants. I was uncomfortable; the area before the bridge was run-down, filled with abandoned buildings. Would the park close at night? Would I be stuck on Chouteau Island? Well, if I would be, at least I had my accommodations with me. I walked a bit of the bridge but not enough to see the river. I wish I had, but I needed to be safe.

As I walked back to Sally, people began to arrive. On my drive out car after car passed. It seemed that the island didn’t close, and that the park was the place to be at night.

I think it’s a good thing I left.

It was time to find a place to sleep. My son and his girlfriend told me they’ve slept in hotel parking lots because they’re well-lit. I didn’t know if I wanted to do that. It was getting dark and I needed to figure it out soon. The next day’s drive would be the National Road, which historically ended at Vandalia.

I pulled up Google maps and searched for truck stops. Greenville was close, and there was a Love’s just south of US 40. I backtracked through Edwardsville and Hamel, drove east. When I pulled into the station it was black out. Dozens of semis idled in the truck lot. In the car lot, one stretch said no overnight parking was allowed. I went inside and approached a woman cleaning the hot dog rollers and asked her where I could park overnight. She told me pretty much anywhere but that one row. Okay, I thought. Okay. 

I drove around the lot. Pulled into a spot. Drove around the lot and the gas pumps. Pulled into another one. Looked around. Would that one be better? I backed into a spot that was separated from the semi lot by a wide strip of grass. Okay. Okay. I started to climb into the back. Hmm. That semi’s backed up awfully close. What if he backs up more and hits me? I pulled forward and backed into the spot next to it. My new neighbor was much shorter. He wouldn’t hit me. A woman in a large black Grand Cherokee backed into the spot I’d been in and casually, promptly hung her coat over the window and reclined her seat. Okay, so this was a place I could stay. I linked short orange bungee cords across the back seat and hung a blanket over them. Stuck a towel in the window. Sat with my head hunched over because my ponytail hit the ceiling, and when I’d get to close to the bungee cords they’d grab strands and I’d be stuck. After taking my contacts out, changing into something comfortable for sleep, and setting my $6.99 battery-operated fan on top of the cooler, I finally lay down.

It wasn’t comfortable. It wasn’t entirely uncomfortable, but this side-sleeper should have thought to bring more padding for her bony hips. Finally, I fell asleep.

Driving Route 66 in Illinois

Route 66 is the stuff of movies, music, and lore. It’s part of the American vernacular and epitomizes the freedom of the open road. When the route became official in 1926, the planners decided it should go through small towns. Today, that decision means that anyone driving Route 66 can skip the homogeneity of the highway and see what the U.S. is really like. 

If you want to learn more about the attractions and things to do along Route 66 in Illinois, get your copy of Midwest Road Trip Adventures. This fun anthology will be out at the end of November, 2020. Pre-order your copy now and I’ll autograph it. I’ll also send you send you a FREE e-book of Ultimate Road Trip Guide and Planner! I’m massively expanding the current 60-page guide into a full-fledged book, and that will be out by the end of the year. (Chemo treatments willing!)

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