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When we told people we were heading to Milwaukee for Memorial Weekend, the response was almost universally the same: Why?
Here’s the thing — we’d been before, almost by accident. A few years ago we ended up spending a night there after Wisconsin Badgers football sent Madison hotel prices into the stratosphere. We had a genuinely great time. So this time, we went on purpose.
Where We Stayed: Drury Plaza Hotel
Where We Stayed: Drury Plaza HotelWe booked the Drury Plaza Hotel right in the heart of downtown. If you haven’t encountered Drury before, they include a free hot breakfast and an evening “Kickback” — nightly drinks (yes, including mixed cocktails) plus enough food to function as dinner if you want it to. We had dinner reservations both nights so we treated it as happy hour, but the value is hard to argue with. We’ll be looking for Drury locations everywhere we travel now.
Day One: Architecture, Coffee, and a Truly Enormous Mozzarella Stick
We found an architecture walking tour through Historic Milwaukee for around $15 a person and it turned out to be the perfect way to orient ourselves. Milwaukee has a genuinely eclectic mix of buildings — German-influenced, Parisian-looking, an early proto-data-center wrapped in fiber optic cable — that we’d have walked right past without context. The tour ended near the Milwaukee Art Museum, designed by Santiago Calatrava (same architect behind the famous Zubizuri bridge in Bilbao). Worth seeing even from the outside.
Before the tour, we stopped at Discourse Coffee, a hip coffee shop affiliated with Milwaukee Public Radio. Adventurous signature lattes. Bitters and citrus were involved. We liked it.
After, we hit the Third Street Market Hall — one of those modern food halls popping up everywhere — and ordered what may have been billed as the world’s largest mozzarella stick. It arrived in a pizza box. We have no further questions.
That evening we drove to Wauwatosa for dinner Buckatabon Tavern & Supper Club. The food was good. Our kayak guide the next day confirmed it was not, in fact, a real supper club. We’re still searching. We did, however, have our first Wisconsin old fashioned — brandy instead of whiskey, topped with your choice of sweet, sour, or push. Go sour (that’s Squirt). Trust us.
Day Two: Kayaking the River
Brew City Kayak offers guided tours up the Milwaukee River and back, and it was one of the highlights of the trip. The city looks completely different from the water. We learned more Milwaukee history in two hours than we had all of the previous day. We also learned that hot tub boats exist and that Milwaukee has one.
Afterward, we made our way to Boone & Crockett, a cocktail bar where specialty drinks are $7 all day on Sundays. Creative cocktails. Genuinely great bar. Wisconsin alcohol prices remain undefeated.
Dinner was at Mader’s, Milwaukee’s classic German restaurant. We ordered the Taste of Germany for two — schnitzel, sauerbraten, Kessler chop, pork shank, spaetzle, potato salad, cabbage. We took half of it home. It was a lot of meat, and it was fantastic.
Don’t Miss: The Bronze Fonz
On the Milwaukee Riverwalk, there is a life-size bronze statue of Henry Winkler as the Fonz. TV Land commissioned it, then backed out. The city paid for it themselves. He is smaller than you’d expect. People take photos with him; most of the children do not know who he is.
Mars Cheese Castle (On Your Way Home)
If you’re driving back toward Michigan, stop at the Mars Cheese Castle in Kenosha. Fresh cheese curds, string cheese, Wisconsin wines, bratwurst, and an on-site tavern. Technically a tourist stop. Genuinely worth it.
Milwaukee doesn’t show up on a lot of weekend trip radar, and we genuinely don’t understand why. Good food, a beautiful riverwalk, interesting architecture, a great cocktail scene. It’s walkable, unpretentious, and right on the lake. If you’re within driving distance, give it a long weekend
Thanks for stopping by! Check out our Go See Do Explore Podcast, available wherever you listen to podcasts. To read about some of our previous trips, visit my Trips Page. If you like my photos be sure to “like” my Facebook Page and follow me on Instagram! For my list of gadgets to make your travels easier, click here.