October 30th 2026 - Fall travels to Chicago and Wisconsin - Chicago to Madison - 3.3 miles hike with minimal elevation gain
Friday:
One of the parts of our trip logistics that was harder to figure out was how to get to O’Hare to pick up the rental car. Since I wanted to get the day started as early as possible, I would have preferred to take the L to O’Hare and head out from there. Unfortunately we had too much luggage to realistically navigate public transit at rush hour. In the end I decided to that the conventional answer was probably the best answer. Take a Lyft to the airport with all our stuff. The trip to the airport wasn’t terribly congested but it wasn’t fast either. Thankfully we were dropped off right in front of the ‘multi-modal center’ which houses the rentals so we had just a short walk to get to the Enterprise office. There was absolutely no line and we were in a brand new Kia Carnival with 54 miles on the odometer in just minutes.
We had breakfast at a bagel shop/deli in Buffalo Grove IL. We also tried to find a coin laundry but our initial attempt at that wasn’t successful so we decided to wait on laundry until we got to the hotel in Madison. I picked out at trail at Moraine Hills State Park near McHenry Illinois and we enjoyed the fresh air and easy wide trail with crunchy leaves and plenty of end-of-fall color.
The rest of the drive to Madison went smoothly and, after a bit of a wait, we were checked into our 2 King Bed Suite room at the Embassy Suites downtown. I started laundry washing while we waited for our room to be cleaned. For dinner we went with a cheap casual favorite that Brian and I miss being able to go to, Noddles & Company. On the way we took in some of the sights along Madison’s famous pedestrian focused State Street including checking out their new Museum of Contemporary Art. What a stunning space! There was a fascinating exhibit in the lobby with 3 large video monitors that rotated in opposite directions slowly. A control panel mounted a few feet away allows you to change both the images shown and the hue or color palette used in the images. It’s all very slick and smooth and the colors on the displays are so saturated they look like wet paint. The museum also has a stunning large glass staircase leading to the 2nd floor and the stunning rooftop deck. All of this was open, accessible and free to explore. There were very few people in the museum and it felt like we were just trusted to poke around as we pleased. The rooftop garden puts you at a great vantage point to see the Orpheum Theater sign and other sites along State Street. And this was exactly across the street from dinner so it was very convenient.
The bar, Woofs, was absolutely joyous, just as it has been all 3 times we’re been there in the last year or so. We met a number of people, had laughs and fantastic cocktails. Our favorite bartender was there and some people were in costumes. It’s hard to express how deeply satisfying it is to have an engaging embracing fun time out with other gay men. There are (gay) bars all over the place but for the vast majority of bars and the vast majority of visits they are, at best, hook-up opportunities (for those who are there for that) and an alcohol dispensary for the rest of us. The very best bar visit I had in Rochester in the 7 years or whatever we lived near there was a long conversation with a guy who was once in prison and was working at a Cajun restaurant. That is, to be charitable, a very low-bar to clear. Woofs reminds me of the very best visits from long ago to the Lone Star in San Francisco many years ago.
Saturday:
Brian and Jim were sending clear messages that they didn’t want another busy day walking a lot in Madison. My left food is actually starting to chafe from the 52 thousand steps we’ve had in the last 3 days so I don’t think the idea of a ‘down day’ is so terrible. But what exactly we will do with our last day in Madison remains to be seen. For now, I told Brian and Jim that I would eat alone when I inevitably got up hours earlier than they did. To that end I passed up on the very complete but pedestrian breakfast offered by Embassy Suites and walked half a block to Marigold Kitchen. The chorizo breakfast bowl I had was the best tasting and most nourishing feeling breakfast I’ve had since I was in California for a conference about 5 years ago eating Huevos Rancheros on the beachfront patio of the Hyatt in Huntington Beach. I also had an eye-rollingly great cookie with Biscoff and chocolate chunks that I’m very tempted to go get another of to share with Brian.

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