Ride 16: Wisconsin
The Badger State

State: Wisconsin (#16)
Area: Madison
Route: Loop around the city on its extensive trail system; highlights included Lake Monona, wildlife and nature preserves, the UW campus, and the state capitol
Final Mileage: 50.85
Date: September 1, 2023
We’ve officially arrived at a new phase of this project: expanding beyond the eastern seaboard and into the Midwest.1 With Alex’s move to Springfield, IL, we’re now well positioned to conquer a new set of states. For this round, we decided to do our second double-header, landing on the great states of Wisconsin and Minnesota.
This tandem was the perfect candidate for several reasons. Both are within driving distance for Alex, and Chicago’s airports, which are on the way from Springfield to Wisconsin, made it easy for Alex to pick up Michael on the way. Both states are home to cities with solid biking infrastructures that made it easy to plan routes—cities that are only a few hours’ drive apart. And perhaps most importantly: each of us knew people on the ground in these places.
In fact, our socializing began before the trip even started when one of Alex’s friends from Kansas City decided he would join for both rides! Bing (whom some of you may remember from our Kansas ride) tagged along for the road trip, joining Alex as they picked up Michael from Chicago-Midway and continued onto the Wisconsin state capitol, Madison, for the first of the two rides.
Both of us also have local ties to Madison. One of Alex’s med school friends had relocated there recently, and Michael has long had family connections in the area. The latter led to another great addition on this trip: Michael’s parents decided to drive up to spend time with our crew and see their family while in the state!
After a lovely Thursday evening dinner at Sol’s on the Square and post-dinner drinks at Eno Vino, we all turned in so the three riders could rest up before setting sail in the morning.2
Our route for this ride was fairly tame—it didn’t include significant elevation change or rocky roads—and featured stunning scenery throughout. We patched together several trails that took us around much of the city south of Lake Mendota, including around Lake Monona, beautiful wildlife and nature preserves, the University of Wisconsin campus, and the state capitol.
We started from Michael’s family’s Airbnb near Lake Monona and headed south. Much of the first stretch of this ride was on suburban streets as we headed for (literally) greener pastures. After about seven miles, we finally hit Lake Waubesa, and thus began the bulk of our ride on Madison’s extensive trail system. (The following pictures don’t really do these areas justice, but believe us when we say they were absolutely gorgeous in person.)
Although our surroundings were pretty and the course was relatively flat, we did experience a few challenges on the route. For starters, the Midwest had been coming off of a heat wave that we’d been keeping an eye on all week. By the time we arrived in Wisconsin, it had thankfully dissipated quite a bit, but the highs that week were still reaching the low 90s. We ultimately decided to start the ride early in the morning while it was still cool and clock as many miles as we could before it got toasty.
It’s also probably worth mentioning at this point that our trip to the upper Midwest very nearly didn’t happen! Alex got hit with a case of something gross the previous weekend that took him out of commission for a couple of days. Fortunately, given the relatively early timing of the illness, it had passed by mid-week and we were able to proceed with everything as planned. However, there was still some lingering fatigue that made the early going of this ride somewhat difficult. (He was a trooper and gutted it out for a while anyway.)
Thankfully, a couple (belated) Ibuprofen tablets and some delectable food at Mickie’s Dairy Bar set everything right, and the final stretch of the ride went much more smoothly.
By lunch, we had completed 37 miles, leaving us with only a fraction of the ride left to do as the sun became a little more oppressive. So we took off for the UW campus. As it happens, the school was in the middle of move-in weekend, meaning the grounds were abuzz with students cheerfully socializing and preparing for the fall semester.
At this point, we were in the home stretch. From the campus, we headed to our final point of interest: the state capitol building. On our way there, we rounded the Monona Bay, whose adjacent roads were lined with beautiful homes overlooking the water with a direct view of the capitol and downtown across the way.
After navigating some unexpected construction in downtown, we finally made our way to the top of the hill to the state’s seat of government.
We then took the Capital City Trail to the Airbnb, where we celebrated the end of our 16th 50-miler! To round out our time in Madison, Michael’s parents joined the three of us for dinner on State Street—a multi-block pedestrian area filled with restaurants and bars that extends from the UW campus to the state capitol. There, we enjoyed a fantastic meal at a place called Taste of Sichuan and post-dinner drinks at a nearby bar called Paul’s Club.
All in all, Madison was a lovely city with a ton of charm and some of the best cycling infrastructure we’ve encountered to this point. Perhaps one day we’ll return for just a for-fun ride and explore even more of what it has to offer.
Yes, we’ve previously done rides in Missouri and Kansas, but those were both near our hometown of Kansas City and very easy to knock out.
Shoutout to Jeremy Busch for his excellent food/drink recommendations for this trip.


















