How to Have the Best Fall Day Trip to Madison Wisconsin from Chicago

The air is crisp and cool. It’s the perfect time for a fall day trip to Madison, Wisconsin. Here is everything I ate, did, and saw. I only had Sunday- less than 24 hours to spend in Madison, Wisconsin. Anna, one of my best friends from high school, was sent on a week-long work trip but had the weekend free. I would have spent the whole weekend with her, but photographing a wedding in Chicago on Saturday- Sunday would have to be enough for the perfect day trip to Madison, Wisconsin.

The day is sunny and beautiful. I leave around 8 am and plan on making it to Madison around 10 am for brunch.

The further I start to drive, the weather begins to change, and it starts to rain; by the time I make it to Madison, it is downright dreary outside, but I am determined to make a good day out of it. I pick up Anna at the house she is staying at, and we head downtown. It’s been a few years since we have seen each other, and we have much catching up to do. The last time we were together was when we were quarantined with our parents in 2020.

She came over to have photoshoots and go on walks. I even bought a kiddy pool to take her portrait submerged in water. Those were exciting times, but now she has an internship that sent her on a trip to Madison, Wisconsin and I moved to Chicago to pursue a career in photography and marketing. It’s nice when worlds can collide again. There is nothing quite like seeing old friends.

Brunch & Coffee at Marigold Cafe

We started the day with a cup of coffee at one of Madison’s many cozy cafes; we decided on Marigold Cafe. The menu has fall-friendly options offering skillets, scrambled eggs, and Pumpkin Spice lattes. We catch up over our brunch and sip on our lattes as we spill the tea of what’s new in our lives. I started dating someone new-. She got a new job.

Tour the Capitol Building

After brunch with a belly full of eggs and coffee, we walk around for a little while. First, we take a tour of the Madison Capitol Building. As someone who interned in Washington D.C. the summer after college, I have always loved the United States Capitol Building, which looks very similar to the Madison State Capitol Building. It’s white with a spherical middle. The flowers outside the building are beginning to bloom. The rain begins to drizzle again, and as we rush inside the building. The interior is dramatic to say the least. I stare up into the ornately crafted ceiling. “Let’s go to the roof”, Anna says.

We walk up a narrow winding staircase to the roof above. The rain had slowed for a little while, and I could feel any drops as we stepped onto the expansive balcony. The balcony path wraps in a circle around the dome part of the building. We take a few laps to see the view below. I see a large fountain. It’s the same fountain I remember hearing stories about. My uncle attended the University of Madison for a few years. He and a few fraternity brothers put soap in the fountain until it bubbled. No one ever got caught but the fountain had to be drained for days.

Rooftop Views

The views from the top allowed us to see part of the campus and the water. The rain, and the fact that it was a Sunday, must have kept the crowds away because Anna and I were the only ones at the top of the building. Just as we decide to head back down, a few families showed up for the tour, but other than that, we were isolated.

Other museums you could see in town are the Chazen Museum of Art or the Wisconsin Historical Museum, but we walk around a do some shopping instead. I am on the hunt to find good Wisconsin cheese.

Day trip to Madison, Wisconsin

Wisconsin Cheese Mart

It doesn’t get better than Wisconsin cheddar. Although I have heard about Wisconsin cheese for as long as I could remember, I have never tasted it, until today. The Wisconsin Cheese Mart has samples of Wisconsin cheese to taste and buy. I try the sharp white cheddar and a sweet desert carmel cheese. I ultimately decide to buy a bag of Wisconsin cheese curds for a snack for later.

Local Downtown

Not ready for our day to end, we walk around Downtown Madison stores and eventually find a Good Style Shop Vintage Shop and Rethreads to pop in for some retail therapy.

Tour the University of Madison Campus and Lake Mendota

Madison is a college town, but that doesn’t mean visitors can’t enjoy the beauty of the campus. Madison has several lakes surrounding it, including Lake Mendota, Lake Monona, and Lake Wingra. While walking, we stop next to a fraternity house with the most incredible views of Lake Mendota. While staying in a greek life fraternityhouse is only something from my nightmares, I wouldn’t have complained about the views of the Lake. Although it’s chilly today, there are some still enjoying a day out on on the water.

Madison Wisconson

It’s getting closer to when I need to drop my friend off at the airport, so we say goodbye to downtown Madison. Although there are other things I would love to see in Madison, we only had a day, so this was the perfect day trip from Chicago to Madison, Wisconsin.

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