By Raynee Hamilton. Written for J405 (Creative Journalism). Written Fall 2020
It was early October and I was standing alone, terrified and overwhelmed, on the side of I-290E, the major highway leading East into Chicago. This was a situation that I was fully responsible for getting myself into, having decided that morning that I would try hitchhiking for the first time. I had no real plan, except to see how far away from Madison I could get in a day.
I had never hitchhiked before, but it was on my bucket list because it seemed like a very 1970s thing to do, and I am someone who does things for very stupid reasons. So, armed with nothing but pepper spray and the knowledge I had retained from half reading “On The Road” in high school, I set out. The first car that picked me up was going to Chicago. The driver was heading to his job at a railyard just outside the city. He smoked cigars but didn’t have a lighter - I gave him mine and told him to keep it.
I’d heard that it’s more difficult to catch a ride if you’re in a city, so I asked him to drop me off before he took the last Chicago exit. He pulled over on the shoulder, gave me his number and told me to let him know when I got to my destination. I lied and said I would, grabbed my bag, and got out of the car.
I quickly realized that I-290E is not, in fact, the ideal place to hitchhike from. I made a halfhearted attempt to catch a ride but after getting honked at once I gave up in embarrassment. As I stood on the side of the freeway, dangerously close to the 2,000 pound hunks of metal whizzing by me at 70 miles an hour, I fantasized about getting on a safe, quiet bus back to Madison.
But first I had to deal with the matter at hand, which was that I was stranded on the side of the freeway. I figured that my chances of flagging down a ride were slim, and honestly I didn’t want to stand there any longer than I had to. I made my way up onto the grassy hill that ran alongside the freeway and started my walking tour of the Chicago interstate, hoping I would eventually be able to make it to a more pedestrian friendly area. After traveling under a bridge littered with drug paraphernalia and beer cans, falling down a deceptively steep slope, and stepping in a puddle of water that soaked through my only pair of shoes, I saw a small dirt path that led away from the freeway. Eager to leave my traumatizing experiences on I-290E behind, I followed the path, which led me to railroad tracks where a train was passing by.
While waiting for the train to pass, I realized for the first time how stupid I was. This certainly was not the ‘hitchhiking to Woodstock in 1969’ experience that I had anticipated (I even wore my bell bottoms for historical accuracy!), instead it was overwhelming and stressful, and mostly just a lot more effort than it was worth. It was also during this time that I realized how dangerous this adventure probably was, I was a 125 pound 19 year old girl who was willingly getting into cars with strange men who could almost certainly murder me if they really wanted to. It’s not that I was worried about getting murdered as much as I was worried about what newspapers would write about me after the fact. “Idiot girl killed while trying to be Jack Keroac”, I imagined the headlines would read.
But, I was already in Chicago and it wasn’t even noon yet, so I decided to keep going. I followed the train tracks as they led me away from the highway and into a residential area, where I spotted a water tower that let me know I was in Elmhurst. This was also when I remembered that I had a cell phone with google maps on it (suck it, Jack Keroac), which proved to make the whole hitchhiking thing a lot easier. I found the nearest freeway exit that looked like it would take me south towards Indiana, and headed that direction.
One thing I had learned about hitchhiking from the wikihow article titled “How to Hitchhike” (it was actually quite useful, I swear!) is that people are more likely to pick you up if you have a sign that says, in a general sense, where you are trying to go. So, that’s why I ended up dumpster diving for a sign-worthy piece of cardboard in the recycling behind a Shell gas station in Elmhurst, Illinois. I found my cardboard, wrote “Gary, Indiana”, and headed to the I-294 freeway exit which led southeast into Indiana.
Freeway exits are the best place to hitchhike from, in my limited experience - there are usually traffic lights, which means cars move slower and have time to see you and stop. I stood on the sidewalk next to the traffic lights for about 20 minutes, long enough for me to get impatient and start looking up the nearest bus I could take back to madison, when a woman in a white truck leaned out her window and told me she was headed to Gary if I wanted a ride. I got in the truck and she immediately turned to me and, in an incredibly midwestern accent, asked me “what the hell are you going to Gary, Indiana for?”, which is the only acceptable thing to ask a person who is hitchhiking to Gary, Indiana.