Day 26: Out of Beverly Shores and along Lakeshore Drive into Chicago…which is on the shore

Riding into Chicago was a big day. It’s among my favorite cities, and after all I’ve been through on the bike, I couldn’t wait to ride into the best skyline in the world. To do that I had to leave the beautiful Beverly Shores and ride through the less beautiful industrial towns south of Chicago. 

In the morning Geoff rode out with me: he went to work, I went back to the beach we met at the night before. I wasn’t ready to say goodbye to the peaceful beach just yet. I thought about how it’s going to be my last time being around such a large body of water until I make the Pacific. Thinking like this used to make me anxious and intimidated by the thousands of miles. At this point I just have a steady resolve. 

I could just make out the skyline 53 miles away, and got very excited. I couldn’t quite grab a picture of it though. I did manage to get one of the playful warning about lake currents though:

I cruised along the beach for a few miles, taking my time, soaking it up, until I made it to US-12, which would take me all the way into the city. 

I made it past the South Shore Line train station in Dune Park, and I knew I was entering the metro area. 

And then the first sign is be going through Gary, IN. 

Time and time again I get warned about going through the dangerous, worn down towns that industry left behind that are outside of major cities. I got quite a few warnings about Gary, and here’s what happened:

I got welcomed.  

I saw a gutted hotel. 

I had empty roads along train tracks.

I saw City Hall.

I saw the sign to a business that no longer exists. 

I saw yet another massive industrial operation.

And that was it. People hold on to fears of these “problem cities” so tightly, yet I never feel unsafe or anything close to it. There’s hardly anyone in them to hassle me anyway. 

So then off to East Chicago:


The only thing that made me uncomfortable through here was some sort of celebratory tank on the side of the road. 

To be sure, these towns seem to be in pretty rough shape, and they hardly made for scenic riding. But there’s no way to avoid them if I want to ride in big cities, which I very much do. Even though they aren’t always the most beautiful, these towns are part of the landscape I’m conquering one pedal stroke at a time, and you can’t separate the sludge from the glamor. For every Times Square or National Mall there’s a Newark or Baltimore. By riding through it all I’m better able to see how the built environment is all interconnected, which is exactly what I wanted when I planned this all out. 

Illinois was the second state in a row that didn’t have a welcome sign for me, which bummed me out a little. The best I could get was this:

US-12 took me inland a bit and my anticipation was growing more and more to get into the city. I was making great time, which I figured was a function of my increased fitness and my excitement for the city up the road. But then I saw the sign I wanted:

Almost back to that big beautiful lake. 

Before long I made it to Rainbow Beach on the south side of the city. Whatever exhaustion I pushed through was worth it to get this view:

I just kept saying “wow” to myself like a little kid opening birthday gifts. I was tickled. I’ve driven in to Chicsgo so many times, and the skyline scratching the sky is always a beacon for good times. But on a bike, after more than a thousand miles since leaving New York, I just let the cool lake breeze blow over me while I was consumed with a profound sense of satisfaction. 

After a healthy break on a bench I pushed on through the south side of Chicago, another “problem area”:

Yes, I made it through just fine. 

I passed the Museum of Science and Industry:

As that skyline got bigger…

And bigger…

Until I was off Lakshore Trail and crossing under Michigan Avenue on my way to Pilsen, where my hosts Kaitie and Bethany live. 

They were amazing from before we met, saving a set of keys in a lock box for me to get in and clean up before they got back from work. Lugging 60 pounds of gear up to a third floor walk up isn’t exactly my favorite way to end 55 miles into a headwind, but I didn’t care. I was in Chicago and I cleaned up in the shower and stretched out on the couch feeling fantastic. It felt like a homecoming of sorts, although I’ve never lived in Chicago (yet…). What added to the smiles was knowing that I had the next day off the bike, free to enjoy one of the world’s great cities. I also felt very good about not feeling too spent: I was in much better shape comin into this rest day as opposed to the last two. I’ve really noticed an increase in my body’s ability to function. Stands to reason I guess, but feeling it is a whole different animal. 

Kaitie came home and it already felt like I was in the company of a friend, as we had been texting a bit in the days previous. She invited me to join her to her regular Monday night cookout with her friends in Bridgemont, about 20 minutes on the bike away. This meant I had to get back in the bike, which I wasn’t crazy about. But it was fantastic riding through the city like a local, with a local. Kaitie is a fearless, uncompromising city rider, and trying to keep up was humbling. But before I could kick myself I remembered that I had ridden there from New York and felt a bit better about it. 

Although I was tired it was great hanging out with Kaitie’s friends. We talked a lot about my tour but there was even more teacher talk; Kaitie teaches elementary and so do a couple of her friends, so I put the now dusty teacher hat back on to talk a little shop. The best part was being around young people. My hosts have been incredible all along, but it was a breath of fresh air being around a crowd in their mid/late 20s. I’ve really enjoyed Warmshowers for being around people on my solo endeavor but I made the decision then that whenever I look for potential hosts I’m going to try to mix up the demographics a bit to keep things interesting. 

The night wore thin, then it was back to Pilsen, where I crashed out on the couch, content to be in Chicago, and ready for Chicago fun the next day. 


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