Madison and Milwaukee, Wisconsin are two great cities around the corner from Chicago worth jumping in the car to see over the course of a day. The State Capitol in Madison is the second tallest and offers a 360 degree view of the city!
Madison, Wisconsin Highlights for Saturday, October 7:
- University of Wisconsin-Madison
- Michelangelo’s, coffee shop
- Market in Capitol Square (Saturdays only)
- State Capitol rooftop
- State Street
- Thai Pavilion in the Olbrich Botanical Garden
As soon as we arrived at Chicago O’Hare (ORD) airport at 7 am, we took the Budget-Avis shuttle to get our rental car and hit the road for Madison, Wisconsin. Luckily, I found an amazing car rental deal through CarRental.com days before our trip (under $72 for 3 days)! The fastest route is taking a toll road, so having cash is key! It cost less than $10 across 4-5 toll booths which are located on the right side of the road when it splits. When we arrived in Madison, we drove through the University of Wisconsin-Madison campus, which is beautiful! One amazing thing is there is tons of free parking on campus during the weekends and it’s walking distance from all of the sites. Click here for a list. We parked in “Lot 26” which was along the main road, directly outside the Observatory and had a front row view of Lake Mendota.
We walked down to the lake and over by the Memorial Union Terrace. There are lots of nice boats docked and seating to take in the scene. You can also pose for a picture with UW’s mascot, the badger. 
We walked along Langdon Street to see a lot of Greek houses before making our way toward Capitol Square. I spotted Michelangelo’s, an artsy, large coffee shop which has two entrances. 
The specialty menu is really unique as it’s made up of drinks created by current and former employees. I tried the “espresso miel” which was a latte of honey and cinnamon that I enjoyed!
On Saturdays, there is a large market (Dane County’s Farmers Market) that starts early and usually ends by 1:30 pm in Capitol Square. This is the area that surrounds the State Capitol, which is the second tallest one in the U.S. (behind Louisiana). While I didn’t have a chance to try it myself, Stella’s Bakery is a popular offering. Exploring the Capitol is a must! The rotunda is beautiful, you can explore on multiple floors (with or without a guided tour) and the bathrooms are clean. Plus, it seems like a well-kept secret, but you can find the spiral staircase to the rooftop and enjoy a 360 degree view of Madison for free. This was a highlight for us. From here, walking along State Street is ideal as there are lots of shops, restaurants and bars before you return back to UW-M’s campus. If you’re a bookstore person, definitely check out A Room of One’s Own.
Once you’re back at your car, take the 15 minute ride to the Olbrich Botanical Gardens.
It’s free to walk around and there’s a beautiful Thai Pavilion that was donated by the Thai government.We accomplished this itinerary and a few other spots in about 5 hours. If you have more time, some other ideas would be to rent bikes and explore the lakes along the paved bike paths, take in the view of the city from Olin Park or check out the places along Williamson (“Willie”) Street.
Milwaukee, Wisconsin Highlights for Saturday, October 7:
- Milwaukee Public Market
- Milwaukee Riverwalk and Art
- View from Veterans Park
The drive from Madison to Milwaukee was very easy, under 90 minutes and toll free. It was raining when we arrived, but stopped shortly after. We found free parking near Van Buren and Michigan Avenue. The location was great because it was walking distance to the Milwaukee Public Market in the Historic Third Ward.
The market is small, but has a good variety. I tried the bee at Anodyne, saw the around the world market clocks and got a classic picture of the “Milwaukee Public Market” sign.
Milwaukee is very walkable and it’s only a few blocks to the Milwaukee River. All along the river you’ll find public art such as Rosie the duck, the Bronze Fonz, a statue of Arthur Fonzarelli from Happy Days and other artistic pieces. 
I recommend timing your walk close to sunset so you can enjoy the colorful sky and reflections on the water. We were particularly lucky because a little boy called out a rainbow that appeared near the duck family statues.
Break from the main path to see the Old World Third Street. Before starting our drive to Chicago, we drove to Veterans Park for a short walk which has a lovely view of the city and would also be a great place for the sunset along Lake Michigan.
Be sure to check out my next entry on our two days in Chicago that followed.
Treat Yourself to Travel 