Afternoon Tea, ABBA, and Endless Wandering: A Weekend In Milwaukee

Category: Travel
October 6, 2026

Growing up just North of Milwaukee, I had an idea that the city was industrial, gross, and maybe a little dangerous. I’m not sure this was a fair assessment, but I’m happy to say that 20 years later, it’s time for that reputation to go away. The Milwaukee I spent a weekend in recently with my two teenage daughters is walkable, beautiful in places, rich in culture and history, and full of the kind of unplanned moments that make a girls’ weekend memorable long after it’s over.

If you’ve been avoiding Milwaukee, it might be time to think again.

Going Off-Script: The Milwaukee Art Museum Opens Its Wings

This weekend, we’d only planned only two things: Afternoon Tea at the Pfister Hotel and a matinee show of Mamma Mia!

Saturday morning, we took a long walk along the lakefront, which is wonderful. You can be on a prairie, lakeside path and still see all of downtown or turn around and there’s Lake Michigan stretching out as far as the eye can see. We happened to be walking back past the Milwaukee Art Museum right at 10am, when it opens its beautiful wings, like a floating ray.

The Milwaukee Art Museum

The Milwaukee Art Museum’s Quadracci Pavilion, designed by Santiago Calatrava, has a moveable sunscreen called the Burke Brise Soleil: two enormous white fins that open and close like the wings of a massive bird, twice a day if it’s not too windy. I remember it being a big deal when it opened in 2001. Everyone thought the wings would just break, but here they are, 25 years later, still drawing a crowd every day at 10am.

The Federal Courthouse and a Chance Encounter with Justice

On a complete whim, we decided to take advantage of Milwaukee’s Doors Open weekend, where many historic buildings open their doors for free tours all over the city. When we saw this castle-like building with a small crowd gathering to go inside, we stopped to ask the docent what it was.

Milwaukee’s Federal Courthouse

He was clearly surprised we didn’t know, but we were invited right inside, through the metal detectors and into a giant sun-drenched atrium. This is Milwaukee’s Federal Courthouse and it is a beautiful building, filled with courtrooms and offices, that is not normally open to the public.

The Courthouse Atrium

What we didn’t expect was to end up in a small courtroom hearing a lecture from Chief Justice Pepper, a U.S. District Court judge, who talked with us about her work: the complexity of it, what she handled, and what she didn’t. Unlike what you often hear about judges in the news today, you could tell she took her job very seriously and she restored my faith in the judicial system a tiny bit. She’s got an interesting, yet grueling job.

I also took the opportunity to let Senator Ron Johnson’s staffer know, in no uncertain terms, how I feel about his representation of Wisconsin. His staffer seemed to take my comments and concerns seriously, but just like every other time I’ve called, I’m sure I won’t hear back.

Afternoon Tea at the Pfister

After our unexpectedly neat walk in the morning, it was time for Afternoon Tea at the Pfister Hotel, one of Milwaukee’s great historic landmarks. The Pfister is incredible inside. There were several swanky weddings taking place on Saturday and one of them took over the entire Victorian lobby. Tea was on the top floor with a beautiful view of Lake Michigan and the surrounding city.

Afternoon Tea at the Pfister Hotel

Afternoon tea remains one of my favorite things to do and I’ve happily introduced my girls to it. Pfister’s tea is quite good. The tea presentation and selection from Rishi Tea is wonderful and the food is delicious. I’m planning to come back in December for their holiday tea.

Third Street Market and the Night Walk

After tea, we were ready for a rest and so we spent the remainder of the afternoon reading in our room and relaxing in our hotel hot tub. When we finally got hungry again, we made our way to the Third Street Market Hall, which has a lovely mix of food stalls. Everything from sushi to burgers. Everyone in your group is sure to find something they want without anyone having to compromise.

The Third Street Market Hall is not the only good, indoor market in Milwaukee either. After dinner, we took a night walk along the river, and saw gorgeous light displays, boats passing, and the other market hall: Milwaukee Public Market. We didn’t go in this time, but I’ve been there a few times and it is one of my parents’ favorite places to go.

Milwaukee Public Market

Mamma Mia! at the Marcus Uihlein

Sunday was brunch, then Mamma Mia! at the Marcus Uihlein Hall.

Marcus Uihlein Hall

The show was joyful, ridiculous, and very fun and the cast was excellent. After the final bow, when we had already given the cast a standing ovation and started mentally preparing to leave, they came back out and played three more numbers, including Dancing Queen.

Just so we could dance. It was awesome. What a fun show!

Milwaukee Is Worth a Trip

I never think of Milwaukee as a destination. It is only an hour and a half away and I often feel like I’ve been there and done that. But the city we wandered through this weekend: the lakefront, the art museum, the courthouse, the riverfront at night, tons of historic, interesting buildings, and the theater full of people dancing to ABBA is not the city I thought I knew.

Milwaukee seems to be a city that rewards wandering. The weekend with my kids was wonderful. The planned parts were great. The parts we stumbled into will not be forgotten any time soon.


Have you been to Milwaukee recently? I’d love to hear what you found when you went off-script. Drop your recommendations in the comments.

Search the Blog

Subscribe to Blog via Email

Enter your email address to subscribe to this blog. We will never share your email.

About Amber Field

Amber has over 20 years of experience working in the software industry with agile software teams and specializes in creating efficient, happy teams & clients while helping them scale, execute, and work / live intentionally.
Get to know Amber →

Check Amber Out On:

Browse Posts by Category

Recent Posts

Retiring Early When You Still Have Kids at Home

Retiring Early When You Still Have Kids at Home

Most retirement content (books, podcasts, financial planning guides) is written for people whose kids have left the nest. The vision it sells is the same as the one I had going in: extended travel, leisurely mornings, and complete control over your calendar. You do get some of that. It’s just not the whole picture when you have to get someone to dance at 6pm.

read more
Jane Austen’s Bookshelf by Rebecca Romney Is The Gift That Keeps on Giving

Jane Austen’s Bookshelf by Rebecca Romney Is The Gift That Keeps on Giving

Romney’s book, Jane Austen’s Bookshelf, is incredibly well-written and eye-opening. Somewhere between her descriptions of the fascinating world of rare book dealing and her excavation of the lives and hardships of famous female authors of the 1700s and 1800s, I realized something that stopped me cold: we have let men curate so much more than just our decisions about what to read. I quickly gave this book five stars. Here’s why you might like to read it too.

read more
How to Shed Obligations When You’re Feeling Overwhelmed

How to Shed Obligations When You’re Feeling Overwhelmed

I’ve been feeling a bit overwhelmed recently. What I’ve learned, after years of accumulating obligations and then having to shed them, is that the solution isn’t to be more disciplined about saying no in the future. It’s to do a periodic audit of everything you’ve already said yes to and then make some harder decisions than you made the first time around.

read more