Milwaukee & Chicago Travel
I don’t know much about Milwaukee.
My earliest recollection of the area comes from Frasier. Rozz Doyle, (Played by Perri Gilpin) is from Wisconsin and her mother was a high ranking political official there. Rozz makes a joke about cheese. From there I know that Milwaukee, WI is part of the cheese capital of the world. That’s about it. I never even thought Black people lived there.
It wasn’t until a some 20 years later that I became friends with someone from there that I realize, the nicest people are from Milwaukee. OK, this is barring a serial killer who shall not be named.
Let’s Take a Trip
My Milwaukee friend says to me; let’s take a trip. We can hang out in the Ill Mill (Milwaukee) for the day and head to Chicago the next.
Your girl is always down for an adventure, and though I’d been to Chicago many times on business, I’ve never been to Milwaukee. Always up for a new experience, I agree to take the trip to Milwaukee.
It’s crazy too – the trip wasn’t a me and him thing – I was meeting his friends. I hate meeting new people. It pulls at my deepest of insecurities. I’m a trooper though. Plus time spent hanging with him is worth its weight in gold. I’ve got to put those, “will they like me” questions to the side to spend time with a friend and explore a new city.
The Milwaukee Experience
Flying into Milwaukee, felt like flying into NYC’s LaGuardia airport. You’re essentially flying into a city over a body of water. I learn that Milwaukee is nestled right alongside Lake Michigan.
As soon as I get to the airport, my friend calls me to give me a short tour of his city before I check in.
To be completely honest, I’m a little annoyed. Looking rough in my flight gear, I want a chance to make it to the hotel to beg for an early check-in to get spruced up before seeing him.
On the flip side though, I land in Milwaukee at 10am. Therefore, I really do need to burn the time before checking into the hotel. He’s right though – seeing a little bit of the city straight from the airport is a good idea.
My friend takes me on a drive through W Capitol Drive in Milwaukee. To my right is beautiful Lake Michigan, where you can see the boating on the lake and folks running. If you like exercise, there are plenty of things to do in Milwaukee.
To my left, are the quaint coffee shops where folks congregate early in the morning to sip a cup and catch up. I think to myself, “I didn’t think Milwaukee was so picturesque.”
He makes a turn onto Lake Drive, where we see a row of expansive mansions. These homes are larger than anything that I could ever think of living in or being able to afford. He says to me: “These houses are where I’ve dreamed of living.” Lake Drive in Wisconsin has the sweet aroma of generational wealth.
What really impresses me are the placards placed outside these beautiful homes.
Although my friend says that WI is a conservative state, these beautiful homes are lined with Biden / Harris signs. Wisconsin may be a conservative state, but this street is Democratic.
When I see a Black Lives Matter sign firmly affixed on a University of Wisconsin – Milwaukee dorm; I nearly pass out. My expectation of Milwaukee is White & conservative. From what I saw and the neighborhoods he drives me through – I was dead wrong. My heart grew warm as the drive through the city continues.
His Milwaukee Neighborhood & The Passage of time
One thing he tells me about Milwaukee is that it is a highly segregated city and systemic racism in the from of high property taxes keeps Blacks out of certain neighborhoods.
The drive up Capitol Drive serves as an illustration of his experience growing up in Milwaukee. As he drives up Capitol Drive the neighborhood changes. We leave Lake Michigan and the quaint coffee shops behind for liquor stores and fried chicken spots.
There’s a sharp, palatable change as the mansions become homes in need of desperate maintenance.
He drives by his old house. This is the house where he’s had his earliest experiences. My eyes grow wide.
Remembering his stories about how meticulous his parents were about the upkeep of their homes, I look over at him and ask a question wrapped in a statement – “The house didn’t look like this when your parents owned it, right?” His “HELL NAH” response gave me the answer I seek as I shake my head in disbelief. Saying the house was run down would be a compliment.
He drives me to his grandparents former house next, which isn’t too far from the house he grew up in. Last stop was the park where he used to hoop, which has now been updated. The tour he takes me on shows me his Milwaukee neighborhood and the passage of time. Now in our 40’s, there’s nothing like visiting the neighborhood you grew up in that illustrates that time isn’t standing still.
Chicago Travels
The next day we head to Chicago with his best friend driving. Again, I just hate meeting new people because the fear of being judged hangs on me like a cloak of insecurity.
Knowing this, we take an Uber to a nearby grocery store and he purchases a bottle of Casimigos tequila. That does the trick. By the time his friend picks us up to drive is to Chicago, the tequila slows down my thoughts and quells my unfounded insecurities.
The drive to Milwaukee to Chicago isn’t long and during this time, we talk real life including, the uncertainties of corporate America, the decline of living standards for Black people in Milwaukee and everything else in between.
Expanding Bean’s Gallery of Friends in The Chi
As apprehensive as I was travelling The Chi (Chicago) and meeting his friends, I must admit, it was the experience I needed.
If you’ve read my blog post about expanding my gallery of friends – you’ll see that as a 42 year old woman, I just don’t have many friends my age. My closest friends are my cousins and they are all considerably younger than I am.
Taking that trip to Chicago, we stop to eat at the Hampton Rooftop in Skokie, IL. The amazing rooftop reminds me of what I am missing living in NY. There’s more refreshing conversation with folks my age. I’m finally not the oldest person in the room.
We take a trip to an Amazon and I buy a book: “The Subtle Art of Not Giving a F*CK.” Necessary reading for your girl Bean.
From there we head to another of friend’s condo. The flex was so real. We took shots. Talked some more and then I took a drive with a Queen to get some fried catfish. I was grateful for being around the fellow company of 40 year old’s. By taking this trip, I’m expanding my gallery of friends and I was thankful.
Blissfully Single Bean Keeps It Moving
Granted, COVID-19 has stalled both work and personal travel for me. However, this Blissfully Single Bean is going to keep things moving. While I’m not as mobile as I’d like to be during a pandemic, but those now rare moments that I can take to travel and getaway, I will take them. Life is way to short to not live.
I wonder what my next travel experience will be next? Either camping with the boys or a lake house excursion? Who knows? But time will tell.
Follow me on Instagram and Twitter at beans4reezy to see where I end up next!
Thanks so much for reading!
Blissfully Single and Yours,
