Today I celebrated, or at least achieved, the milestone of working 20 years at Amazon. I woke up and reflected on my time there, typing up a multi-threaded post about the history I had for the past twenty years and what I think may come next. I got my things all packed up, found a local coffee shop I could work from to catch up on photos and post for a minute, before I set out for Chicago.
I stopped by the town of Pontiac, Illinois, where there were several murals painted along the town center. I pulled down one side street and saw this sprawling mural. It was the artist who had done my State Map postcards that I had been sending to myself since Arizona. The mural had paintings of each of the postcards and a portrait of the artist on the wall. Since I was missing a card for California, I thought maybe the Route 66 museum here might have one in its gift shop.
I walk in and the first floor of the museum takes you on a tour of Illinois on Route 66. There is a converted VW Van in the middle of the museum floor. I overheard one of the staff mention that this was Bob Waldmire’s bus, that he drove up and down 66 doing his art. I finally had the name of the artist from my postcards; his designs are hand-drawn maps and points of interest of each state on the Route. The postcards were so detailed yet seemed so simplistic.
The museum had on display tons of his art as well as his personal bus he had converted. The inside of the bus was filled with more of his work and sketches. I now have a new favorite artist, I thought to myself. What I found so interesting was the tiny handwriting, filling every space on the 4×6 cards. [I later read about the fine-point pens that he would use to achieve such tiny writing on the limited space he had].
I went up to the gift shop, where they sold several of his postcards, some in the classic black and white and some done in color. Unfortunately, no California postcard. So I asked the person in the gift shop. She was nice enough to check their extra inventory; she only found other Illinois cars, but none from the other states. I still found other cards I enjoyed sending back home and to family. [I ended up buying the card I was missing from Bob Waldmire’s website.]
After the museum, I called my mom to help reset a password for Ryder’s Facebook account. We ended up talking on the phone for the next couple of hours while I made my way closer to Chicago through farmlands and small towns. It was nice getting to talk with her about the trip, outside the postcards I had been sending home. My mom is and has always been my biggest supporter; it’s where I get my adventurous nature from. She will always support me in whatever I choose to do next with my career after I’m done with this current adventure. I’m missing everyone that are 2,000 miles away. I got off the phone now that I’m entering the Chicago suburbs and need to focus on the directions now.
Since I am driving up from the South but staying North, I figured I might as well drive all the way to the start of the route tonight, which for me is the end. Coming into Chicago, you go through the South Side, Cicero, and such, doing so you get a fantastic view of the Willis Tower at night [formerly the Sears Tower]. Then you cross under the ‘L’ and hit Michigan Ave, then that’s it. Fifteen total days on 66, Santa Monica to Chicago, I made it. Now I’m off to my Airbnb. I’ll come back later this week to the proper end for photos and such.
I’m staying at the same Airbnb I stayed in for a month in 2018. As I came into the apartment, memories flooded back. The place looks the same; this was my last pre-2020 vacation. I fell in love with Chicago on that trip. I open the guest book, flipping back to 2018 and there was my original entry on May 1, 2018. Kind of emotional to read it again, who I was 8 years ago was different, I had just turned 30, now my entire 30s were like a haze. A pandemic, an asshole president, the last 8 years seem like a dream I can’t remember, but the bad parts.
To finish out my night, I go to Cheesy’s down the block (Best Grilled Cheese in Chicago). I went there on my first night back in 2018. I met my bartender, Sarah. I walked in, I asked is the time 10 o’clock or 9? She looked confused, like Is this guy drunk? “What?” she responded. I wanted to know if it was 9 or 10, this time explaining I had been driving for 12 hours and wanted to make sure my phone had actually updated the timezone change. That’s when we started talking about why I drove to Chicago from Washington. In April of all months. I tell her I’m living in a new city for 30 days, an adventure I was planning to start every year. Spoiler: COVID stopped this plan, as I was in Austin, Texas, in March 2020, when COVID took off. 2026 was my first long-term trip since then.
From that point, Cheesy’s was my second home. After days of exploring, I would come in for a drink and food, and tell Sarah of that day’s adventure. I got to know the regulars of the bar, and Sarah was leaving for the West Coast that summer. We kept in touch on socials briefly, and last I knew, she moved back to Chicago.
Anyways, I decompress while I have dinner. This bar is busy with people watching football. I reflect on the last 22 days. I paid my bill, and the bartender gave me a free beer. Just like Sarah had. I go walk around and take in the city and get some shots of the neon around the ‘L’ Station.
