One of the biggest recurring themes on this trip is the need to be extremely flexible. Any number of things can instantly flip your schedule on its head. And that’s okay. You might have a mechanical. You might get slowed down because there are a metric ton of hills. Google might send you through someone’s orchard or on a trail that isn’t a trail. In this case, it was the weather.
Our plan was to ride up to Iowa after we wrapped up the Katy Trail. But there were quite a few thunderstorms—and tornadoes—in the forecast. Lucky for us, May is the most active time for tornadoes in the Midwest. So we made the executive decision to skip Iowa altogether. We went to Chicago.
Why Chicago? Good question.
Cortney’s cousin and her beautiful family live there. They had reached out when we first rode into Illinois and extended an invite for us to stay. Also, we’d heard from several people how awesome the cycling is in Wisconsin. We’d never even thought about Wisconsin to be honest, and Milwaukee isn’t far from the Windy City. So there you go.
We rented a truck in Columbia, MO, and drove to O’Hare. Some might find cycling out of one of the nation’s largest airports intimidating, and for good reason. We honestly didn’t know what to expect.
Turns out, the riding couldn’t have been easier.
Sure, it was busy and congested. But there were nice wide shoulders and bike lanes all the way into the city. Crisis averted.
We stayed a couple of nights and were able to spend a day off the bikes. We got the Chicago experience riding the subway, exploring downtown and a few neighborhoods, and even had some brats. (Of course we had brats.)
The best part of Chicago was visiting with family. Extra bonus: Since our niece is a student and lives in town, we were able to spend some time with her as well. It was really special.
As we went further north, the cycling in the Upper Midwest continued to get easier. The route to Milwaukee was almost exclusively car-free bike trails.
The city took this old elevated line (called the 606) and converted it into a landscaped multi-use path. I love it.
About halfway to Milwaukee, we camped along Lake Michigan at Illinois State Beach, just south of the Wisconsin border. It was beautiful.
The trails continued all the way into MKE. And there were tons of cyclists out enjoying the weather.
Cortney and I stayed for a couple days to get some work done and explore a bit. I’m embarrassed to say I didn’t know much about the city other than it’s where Laverne & Shirley made their dreams come true, and it’s the renowned macro brewery capital.
Sadly, there wasn’t a trace of Laverne & Shirley. But we’re happy to report that we also found a thriving beer scene along with The Fonz (aka Arthur Fonzarelli). I guess he loves Milwaukee so much they made him an honorary citizen.
We took the Hank Aaron to Glacial Drumlin State Trails on our way out of the city. At the risk of being repetitive, we discovered more car-free bike paths and rail trails with nice camping options for us. All the way to Madison.
When it comes to a killer bike infrastructure, Portland, OR, is tough to beat. Madison, however, gives it a run for its money. So many people out enjoying the day. So many designated bike lanes and pathways. So impressive for a city of 270,000+.
Our stay in Madison was topped off with a fantastic Warm Showers stay. Hosts N & E were more than generous, sharing beautiful home-cooked meals, homebrew, and bike stories. (Thank you, N & E!)
One of the coolest parts of travel for us is discovering places you didn’t know existed—or hadn’t really thought of—till you got there. This state wasn’t on our radar, but has proven itself an incredible surprise. The people are nice, the scenery is beautiful, and in this moment, the cycling has been outstanding. Nice work, Wisconsin!
Next up: The Driftless Region, more rail trails, and La Crosse.
