A Milwaukee Story

…that of course includes a trip to Chicago.

Krista Marson
Taking Off
9 min readApr 6, 2023

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Milwaukee, photo by author

I actually never really minded having to go back to Milwaukee as often as I did, as there was a certain something about that city which has always intrigued me. Milwaukee is a city that no one seems to watch, and it never surprised me why a person like Jeffrey Dahmer was allowed to happen there. The city flies almost too low under the radar that it sometimes fails to detect its own pulse. I always felt that Milwaukee was there, but it also wasn’t due to the difficulty of adequately identifying it.

Milwaukee was once a beer brewing city, and then it wasn’t. Milwaukee was once a manufacturing city, and then it wasn’t. Milwaukee was once one of the largest cities in the United States, but then everyone moved into the suburbs. The relics of Milwaukee’s former selves was something I always tripped on, and although I always knew who Milwaukee used to be, I was never quite sure who Milwaukee was in the moment. The city’s ambiguity is its most defining feature as well as its greatest asset, although the citizens there often find it difficult to see that way. A city that most resembles an amoeba is nearly impossible to grasp as most people prefer to grab a city by its horns, but Milwaukee doesn’t have any horns to hold on to. Milwaukee doesn’t want nor need to be caught, and it harbors no desire to be corralled like some sort of a Chicago. Milwaukee may suffer a little bit from an identity crisis, but at least it doesn’t carry around a head that’s too big for its body.

If the city was blamed for having a fault, it would be that it’s almost too modest for its own good. Milwaukee has a lot of fine attributes, but since it never boasts about them, one has peel through the city as if it was an onion. It is necessary to tap into one’s inner chef instincts in order to navigate the city properly as one sorts through its many layers of charm.

old buildings, photo by author

My parent’s lived in Milwaukee all of their lives. Before my mom met my dad, I don’t think she ever left the state aside from a few requisite jaunts to go shopping in Chicago. My dad was way more traveled than her only because he did a stint in the navy for a number of years, but whatever traveling he did apparently wasn’t enough to inspire him to want to settle in any other location besides his hometown. Indeed, my dad wasn’t even inspired enough to want to buy any other house aside from the one he grew up in, a fact that he proved when he bought his childhood home off of his mother.

My sister and I followed the same path our dad trailblazed when we walked down the hill to the same elementary school that he once attended back in the day when it was still a one-room schoolhouse. Overall, though, my parents must have had a different connection to their hometown compared to the connection that either my sister or I developed towards it. As far as my sister and I were concerned, Milwaukee was a fine enough of a place to grow up, but it didn’t exert enough of a pull on our heartstrings to want either of us to stay there for the whole of our existences. I can only attribute the difference in attitudes to the generational gap.

Although we all grew up in the same city, we certainly didn’t grow up at the same time. I think the world was smaller when my parents came of age, and they were never taught to yearn for anything beyond what their immediate surroundings could provide. In a way, I’m jealous of their mentalities because they probably expected less out of life than I do. In a world that offers more, it’s natural to think you want everything. My parents were both born when the world was doing with a lot less, so I believe that being born during the depression marked them forever. They learned early on that one doesn’t need very much to live, but I don’t think that society passed down that same lesson to my generation or beyond.

My parents took frugality for granted, whereas I took frugality as punishment. I remember throwing tantrums when I didn’t get what I wanted, and my shrills wouldn’t cease until the object I desired was granted to me. I was definitely born in the wrong era. I absolutely deserved to have been born in the 1930s had karma knew that I was coming.

We never kayaked this river when I was growing up! photo by author

Even though I tried to get away from Milwaukee, my parents were still there and always would be, so I constantly had a reason to go back. It was inevitable that performing the exact same annual pilgrimage got boring to me after a while, so I naturally found it necessary to change things up.

Having a rental car at my disposal was always a good excuse to announce to my mother that it was time for a road trip, and some of my fondest memories of her were the times we spent together riding in the car to someplace new. Oftentimes, however, we wouldn’t end up going very far because she and I both enjoyed looking at buildings, and it was sufficient for us to simply tootle around the historic neighborhoods in Milwaukee and gawk at all the beautiful mansions. We did that tour so often that we both got intimately familiar with all the houses to the degree that when one would change its color, we would judge if it was an improvement or not. The mansions were our secret little joy, and there was never enough of them to satisfy our appetite. We always exhausted the available supply, and there were times when we would drive around to some other random neighborhood just for something to do. I saw so much of Milwaukee due to our joy rides, and I was always surprised by the sheer diversity of houses. That city never failed to disappoint us in our architectural adventures, and it was always our opinion that it was a shame that Frank Lloyd Wright was the only Wisconsin architect that the world had ever heard of. If only all the fine buildings had labels on them telling those who drive by who the architects were, Milwaukee could be dubbed the world’s first drive-through architectural museum.

As it was, my mom and I were left to make our own museum up, and every drive we did deviated a little bit from the last. We stayed in the greater Milwaukee area most of the time, but there was one particular instance when whatever Milwaukee was offering up wasn’t enough to satisfy our mood. One day, we both wanted more, and we were curious to know how many mansions lined the breath of Lake Michigan from Milwaukee to Chicago. Neither of us even knew if there was a road that hugged the lake all the way down to the Windy City, but we were game to find out, so we made a day of it.

good ‘ol Milwaukee, photo by author

I had never driven side streets all the way to Chicago before, although there had been many times when I thought about the possibility of doing so. There are a lot of reasons why someone from Milwaukee really can’t stand a single thing about the entire city of Chicago, but the reason that tops every Milwaukeean’s list is the stupid Illinois toll road that links the two cities together. The action of going back and forth to Chicago requires a physical hemorrhaging of fistfuls of cash in an amount that far exceeds anything dug out of the couch cushions. That toll road should be paved with marble for the amount of money that they have collected through the years, but marble it is not, for it’s just as cruddy as any other Midwestern highway.

So, yes, when my mom and I decided to surface street it all the way to Chicago, I was more than all for it. I was half tempted to roll the window down and leave my hand sticking out, replete with my middle finger flipping off in the direction of the highway as a proud display of my sheer satisfaction with our adventure, but I refrained from doing so only because it was drizzling out.

Milwaukee River view, photo by author

It turned out that our undertaking proved to be a more challenging endeavor than we anticipated. We lost the lake more than we found it, and there was one scary moment when I got so disoriented that I almost ended up on the highway. We really didn’t know what we were doing, but we’d be lying if we didn’t say we had fun doing it. That day remains as my personal benchmark for how many mansions I can possibly drive by in a single afternoon. We kept picking which mansion we wanted to live in, and in the course of three hours, we each must have mentally moved about a dozen times.

I was thankful that looking at houses was something we both enjoyed doing as it was easier to do that than it was to make conversation with her. We both needed a diversion when we spent time together because otherwise, we had a habit of filling our time with arguing. I hated arguing with her, mostly because she had a talent for it. She made an art in complaining about the same crap over and over again, so much so that she managed to utter the same repetitious lines as if they were some new concept that just popped into her head. I don’t know how many times I yelled that I heard her complain about whatever it was before. There was nothing that anyone could do to change the fact that my dad was in a nursing home, but my mom was convinced that yelling about it would somehow magically change the situation. Unfortunately, shouting about it never changed anything aside from making everything more miserable than it had to be.

Milwaukee Art Museum, photo by author

Taking my mom on a mini road trip was often the only remedy I had in my metaphorical pharmaceutical arsenal. Sometimes, having a destination wouldn’t matter, and we would simply drive to nowhere in particular, but other times we would intentionally go someplace specific, usually to an art museum.

I wouldn’t really describe Milwaukee as being some sort of a big art city, but the few art museums it has are more than just decent; they are Chicago-worthy good. Most notably, Milwaukee’s Calatrava-designed art museum is probably something Chicago covets, and they would undoubtedly steal it if it wasn’t cemented to the ground. Admittedly, Milwaukee’s Art Museum looks rather like a fish out of water as it sits on the very edge of the lakefront looking like something a bird just dropped out of its beak, but that’s precisely why I find that building appealing.

The white structure with outstretched wings owns the spot it’s on and rules from its perch with a sense of authority. Though the building may have been dropped there, it has firmly established itself as king of its domain. To go inside that museum is to submit oneself to its rule and experience life as that museum sees it. According to the interior of the Milwaukee Art Museum, the entire world exists inside the belly of a whale where life is surrounded by white and bones, shapes and sizes, light and shadows. Standing anywhere inside that building makes me feel like I have been swallowed whole by a larger entity than myself, and I find that feeling oddly compelling. I like being in that museum, and any exhibit that happened to be on tour while I was there was always an excuse for me to go inside.

There were many times when my mom wasn’t in the mood to go, so I have been alone in that belly of a whale museum enough times that if I actually get swallowed by a whale, the inside of its gut will be familiar territory to me, and I would risk getting a little too comfortable being in there.

Inside the museum, photo by author

My newest quasi-travel memoir Time Traveled is available as e-book or paperback! Buy it either at Amazon or at most major retailers.

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