An Illinois Road Trip Adventure

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.

When my alarm dinged at five I’d already been up for an hour and a half. Not by choice. I was anxious and excited. That day I would leave to drive four of Illinois’ scenic byways. During a pandemic. I didn’t know what to expect. I didn’t even really know how I was going to accomplish it. I had Google maps and a rough idea of where I was going and simply trusted that everything would work out.

Where would I park at night? Where would I go to the bathroom? Those were my main concerns. I packed enough food to last a few days. I put the seat down in the back of my rented SUV, spread out a comforter and a couple blankets, and added a pillow and a sleeping bag. Would it be comfortable? Would I be able to sleep? I have a tendency to jump in and figure things out along the way, but this was extreme even for me.

That would prove to be exhausting. I had to drive into Kentucky one night to find a safe place to sleep. I peed by a corn field. In pit toilets. In port-a-potties. Hiding behind my car in a nature preserve. Crouched in the shadow of an old Texaco station. 

Thank goodness I brought toilet paper.

Sleeping was easier than I thought. The most stressful was the last night when I parked in a hotel parking lot. It was bright, the lot was crowded, and I just knew that somebody was going to knock on my window in the middle of the night and tell me to get out of there. The third night some weird man driving a white box truck kept walking around the parking lot of the Flying J. All four nights I was on constant alert – until I fell asleep. Who could see me sleeping? Could anyone see in? What in the Hell was I doing? Would this be worth it? Yes. I will make it worth it.

I pulled out of our driveway at 6:18 am on Tuesday, June 30. An hour later I was at the Chicago Cultural Center. This was staging; my destination and the official start of my journey would be the intersection of Adams and Michigan, but when I approached it was blocked. A machine broke up the old pavement and tossed 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. “Is this a bad omen?” I wondered. The trip began with a literal road block. I 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. One of them 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

I always do.

Is it luck? Good fortune? Am I blessed? Maybe all, but I think it’s also because I choose to look at each experience as a chance to learn. I can find something good no matter what. That was a coping mechanism for many years. I had to see the good to survive the bad.

Next: Route 66 in Illinois

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