The Route 66 Bike Tour

Recently my Facebook feed brought up a photo album from ten years ago of a bike tour I did from Joliet to St. Louis on America’s historic Route 66. It was the first major trip I had taken since I moved to Chicago almost two years prior. Up to that point I was content exploring Chicago’s neighborhoods and finding things to do in the city. And as fun as it was, it did eventually feel like a normal part of my life. By the early summer of the second year, I was starting to look beyond the city limits for new things to explore. This bike tour in particular was the first multi-day outdoor trip I had ever done, and happened at a time when I was just beginning to find my place in a bigger world. Starting on a dark highway just southwest of the metropolis I had spent two years getting to know, I faced an uncertain future.

The Metra train left the city and made its final stop at the southwest suburb of Joliet in mid-evening on a Tuesday. I wheeled my bike into the platform elevator next to a young guy in a wheelchair. He asked me about my trip and I told him I would get to St. Louis if all goes well. He went on to say that he cycled a century not long ago on a handbike. Then he wished me luck and wheeled in the opposite direction as I turned south, already feeling inspired and challenged.

I rode southward out of Joliet on the main corridor, eventually leaving the last stoplight behind and continuing on into a dark, silent prairie, with no idea how far I would get or where I would stay. There was little to see between the towns other than farmhouses silhouetted on the dark horizon, and occasionally the headlights of a passing car. I soon reached Wilmington and was greeted by the Gemini Giant, the first of many classic landmarks on the route.

Four miles after that was Braidwood, another quiet town in the late summer night. Lights outside of a diner remained open, illuminating icons of an older era.

The interstate was just west of the town, where I turned off from the main road to find a shitty hotel for the night. I found one near the exit, checked in, wheeled my bike into the room, and turned on the TV. A huge rainstorm was closing in, according to the forecast. I went back outside to the far end of the parking lot and looked out at the west across the interstate towards the approaching storm. It was all for the best that I didn’t try to ride any further.

I continued south from Braidwood the next morning. For hours I rode on a straight, flat highway, passing an occasional gas station or diner with Rt. 66 memorabilia. A Polish friend of mine went on a roadtrip in this same place a year later, from Chicago all the way to Santa Monica, and posted all kinds of pictures of landmarks along the way. I told her that if she really wanted to experience my country, that a roadtrip on Route 66 is as American as it gets.

The midday sun was hot as I reached the outskirts of Bloomington, tired from the 70 miles I spent chasing vanishing points on a mostly featureless countryside. When I checked for evidence of chafing, I realized why distance cycling in khaki shorts was a bad idea. I wasn’t in any serious trouble yet, but a rash was starting to form from all of the sweat and friction. It got bad enough that I had to pedal the last 5 miles into the city standing up. I knew there was no way I could go another 200 miles with a ravaged taint, and found a bike shop in town to hopefully get help. The guys there had a good laugh, and sold me a pair of padded bike shorts and bottle of Chamois Butter (or what I like to call Ass Lube).

On a better note, my Couchsurfing host in Bloomington had the most kickass array of old Nintendo gear I’ve ever seen.

I left town the next morning, wondering if I would make any more rookie mistakes, like say, taking the wrong road out of the city. After what ended up being a ten mile detour, I found the main road again and continued southwest. It was more of the same, with long stretches of flat, open road, and a town with a stoplight or two every 30 minutes. I reached Springfield halfway through the day and took the main beltway around it. I continued south on a steady pace, losing track of the little towns and their names as I rode on for hours into the afternoon. I must have gone at least 80 miles so far, yet for some reason I had an endurance that I couldn’t explain. I wasn’t getting tired. I just kept going.

I made it to Carlinville around 6pm and found a good Sicilian pizzeria at the town centre. The hot sun was finally starting to disappear behind the buildings. Maybe it was the nice temperature that put me in such a good mood. Or the boost of protein that gave me such a strong second wind. Or maybe it was the realization that even with my mistakes, this multi-day adventure was coming together without any major problems. Whatever it was, I was going harder than ever on the country road amidst the darkening cornfields, even as the day was coming to an end.

I could have kept going, but I decided to stop in the town of Staunton 20 miles later. St. Louis wasn’t much farther, but I didn’t want to get there at night. I found a hotel on the west edge of town and checked in. From Bloomington to Staunton, I rode 130 miles that day.

A bike path crosses the main road going south out of town. When I reached it the next morning, I decided I had seen enough of Americana and took it into downtown St. Louis.

Route 66 continued west through the city. I rode on for a final hour before reaching the west suburbs where I planned to stay with a Couchsurfing host for the weekend.

I started using Couchsurfing in 2008 when I moved to Chicago and needed a place to stay while I looked for a job. After settling into a routine, I started hosting people, and actively attended weekly bar meetups with the local Chicago group. Over the years, Couchsurfing became my primary way of meeting people when I traveled to new cities. It turned out that my host for the weekend, Tiffany, was also active in the community, and an organizer for the St. Louis Couchcrash that weekend.

A Couchcrash is like a marathon of events that each city does once a year, usually in the summer. From three days up to a week, local organizers schedule bar meetups, walking tours, picnics, house parties, and whatever else they can do to showcase their local scene to the visitors. Many Couchsurfers from out of town come together for the Couchcrashes and tour the cities in big groups, all people of whom share the same ethos of community and travel experiences. You can find events like this in New York, DC, Chicago, Minneapolis, and many other cities (or at least you could before the Covid-19 pandemic banished all of us to Zoom meetings).

That night, Tiffany drove me to their Friday night event at the City Museum, a huge monstrosity of what I could only describe as a jungle gym for grownups. Inside the big downtown building is a network of tunnels, mega-slides, and caves that span over multiple floors. You can find a massive ball pit outside, if you can handle the pain of children throwing watermelon sized balls at your face. And there are even more slides, a ferris wheel, and bus hanging off of the roof. And to top it all off, they have a bar on the bottom floor. A group of us hung around drinking there before exploring the cavern passageways and eventually going to the rooftop to view the city.

We went to a picnic and city zoo the next day, and then met up for a big bar crawl in downtown that night. It was a fun weekend overall, and wouldn’t be the last time I would crash in St. Louis in such a fashion. Throughout this event and others, I became familiar with the network of Couchsurfers who built an online community of travelers in cities across America and elsewhere.

I left Tiffany’s house the next morning and rode to the train station in downtown. I wheeled my bike on the train car for a 5 hour ride back home. I didn’t realize until later that the tire pump in my cargo had the wrong valve… good thing I didn’t get any flats on that trip!

Since then, I continued to take other trips all across Illinois, like the weekend later that year up the Great River Trail on the Mississippi north of the Quad Cities. Or the overnight century in a state park south of Carbondale. Eventually I toured even bigger places out west with a newer bike and better gear. Over time, bicycle touring became just one column among five different things I liked to do. I started to feel like the open road was just one way to go on an adventure. But even more could be explored in the oceans, down the rivers, in the high mountains, and from the sky. Even now, the next adventure is in the forefront of my mind. It never stops.

About Dan Hagen

I’m a guy from Chicago who travels as often as possible. It is my lifelong goal to see the world by train, foot, bicycle, and raft. I like open country roads, urban nightlife, good cuisine, local beer, alpine mountains, wild rivers, and lots of other badass shit. And I will write about it as often as I can.