Mishaps and Misfires: Memorable Moments in Milwaukee

Milwaukee, Wisconsin

Monday, September 26, 2022 - Wednesday, September 28, 2022

Written January 28, 2025

Traveling from Rossford, Ohio – Approx: a 5-3/4 hour drive. This was part of a longer road trip that started and ended on Long Island, NY. It included: Milwaukee, Wisconsin, Chicago, Illinois, and Detroit, Michigan with quick overnight stops in Rossford, Ohio and Drums, PA

A Little Background

Milwaukee has always been high on my list of places to visit. Blame it on 1970’s television, Happy Days, Laverne & Shirley… The Big Ragu…FONZI! They may have been all make-believe, but they were a big part of my childhood. I loved these shows! A second reason was that I had taken a weekend road trip to Rockford, Illinois back in the 90’s once, but no one mentioned that Milwaukee was only 2 hours away. I only found out after I returned to New York, and I was pretty bummed. My early days of planning road trips weren’t exactly spot on, for instance I didn’t know that I needed to drive through Indiana to get to Illinois, found that out by talking to a friend, like 2 nights before I left on that 90’s trip, hah!

While our main reason for this visit was baseball, I had jotted down a few other things I wanted to see and do. For instance, seeing the Bronze Fonz on the Milwaukee Riverwalk. This is a statue of Henry Winkler dressed as his character Fonzi from the 1970’s Happy Days series. As always, I wanted to see something with historic significance, well the hotel I booked our nights for was built in 1907 and was formerly a brick bedding factory, so these places are a good start!

We’re Here!

We arrived in Milwaukee at around 5:30PM and are spending the next two nights at The Ironhorse Hotel, I wouldn’t consider it a large hotel, but it does list 100 rooms and two restaurants. The hotel doesn’t offer parking, but there was a parking garage next door for $15 per 24 hours. Once we checked in and got up to our room, I looked out of our room window and saw that we had a view of the traffic circle that we arrived by. To the right of our window view, I saw covered parking areas for motorcycles in front. That’s kinda neat since we are walking distance from the Harley Davidson Museum.

While unwinding, we talked about where we’d want to go for dinner (Yup, no plan). We really should have gotten right back into the car and drove around to find somewhere to eat, but we had been in the car all day, neither of us were overly eager to climb back in. We also discussed whether to use a shuttle service from one of the local bars to travel to the baseball game the next day. The only bar shuttle we’d used thus far was in St. Louis to get to the Budweiser Biergarten. No decisions were made that night as we both fell asleep.

So, unfortunately, we lost our opportunity to have dinner in Milwaukee, because by the time we were both awake again, it was after midnight. I think if we had gone out at that time, we’d screw up our next day, so the decision although disappointing at the time, was right.

Looking around out the window at midnight, I noticed the prettiest water tower. It was brightly lit and looked like it was surrounded by stained glass. It appeared to be part of the Coakley Brothers building which was on the same circle that I mentioned earlier. The whole area was very clean and quiet. Only one or two cars stopped at the light each time it switched, sometimes no cars at all.

Photo 1: inside our hotel room at Ironhorse hotel

Photo 2: the Coakley Brothers watertower at night

Photo 3: view from outside our hotel window

Aaaayyyyy

The next morning, we woke up early and famished. I think we were out of the hotel before 8:00AM and were taking photos of the Bronze Fonz not that much later. On our way to the Fonz statue, we parked and got out of the car, a worker from the area asked us if we needed help. We were a bit further away from the statue than expected. He pointed us in the right direction, even told us to drive there because it was too cold to be out walking. I thought that was so nice. For reference it was between 40-45 degrees, not cold for the area but maybe cold for how we were dressed.

The Bronze Fonz has water from the Milwaukee River flowing right next to it. Our timing for the Riverwalk probably wasn’t the best. Aside from being a pandemic year, not many stores were open as it was early in the morning, and several were marked as vacant. Additionally, it was a gloomy weekday, windy by the water and chilly in the shade. It would have been nice if we happened upon a breakfast place where we could sit inside and look at the water, but we didn’t come across anything like that on our walk.

We walked around another 60-90 minutes and took photos of the buildings, the water, the plaques and statues in the area. Everything looked so clean and crisp, I couldn’t get over how clean the streets and buildings were.

Photo 1: view of the Milwaukee River along the river walk

Photo 2: the Bronze Fonz

Photo 3: buildings along the Milwaukee river walk

Breakfast/Crisis Averted

Next stop, breakfast! While I had a few places that I had researched, we opted for a place nearby that seemed to be a local chain, Brunch It Up! Although it wasn’t too far away from where we were, we were a bit chilled from our walk, so we warmed up in the car and used the time to drive around and see more of the area. We parked on the street near the restaurant. As my partner went to the parking meter, he realized his credit card wasn’t with him. We did a pretty thorough search around the car wheels and the surrounding area, just in case it fell out when he got out of the car. What started as a decent day was now riddled with anxiety and frustration. Luckily, it didn’t last too long, as the card became visible when we returned from breakfast, it was hiding between the car door and the seat.

Brunch It Up! (or Brunch! as it’s what their sign says), was a sassy, little place. It was a deep and narrow restaurant with bench seating along the left wall and several tables with two additional chairs each facing the bench. There were also a couple of tables with four chairs in the center. We both ordered omelettes with coffee. Looking around at the walls and set up, I couldn’t help but notice how cheery and airy the place was. I thought it would be a nice place to work on a laptop for a few hours. I don’t know if they’d allow that though.

Getting The Lay of The Land

After breakfast, we went back to the hotel to buy tickets to the baseball game and made final plans for transportation to the stadium. On our way we drove by O’Lydia’s Bar & Grill on S. First Street. This was one of the many bars that offered a shuttle to the baseball game, and it was less than ½ a mile from our hotel so we could potentially walk there. Ultimately, we did not choose this, but I think it would have been a lot of fun. We also took a ride over to American Family Field to get a feel for the parking and roads around it.

Pre-Dinner, First Dinner?

By late afternoon, we were a bit snacky, but didn’t want to eat a big meal because we’d left our dinner plans for the Brewers game. Across the traffic circle from the hotel was a place called Conejito’s Place. We decided to walk over. They have a corner entrance and from the outside you could easily miss it. The inside, however, was festive and inviting. As we entered, we saw a long, family-style table with stools in the center of the room. A bar on one side of the room, and a few two-seater tables. We were seated at the end of that table closest to the door, with the bar behind us. The menu was straightforward, and our order was simple, tacos and iced tea. The conversation around us was lively, although we were there a very short time, we both discussed returning the next time we visited Milwaukee.

Photo 1: The Iron Horse Hotel all lit up

Photo 2: inside the check in area of The Iron Horse Hotel

Photo 3: Milwaukee at night

It Was Just Too Short.

Since we did a run-through to the stadium, our drive back and forth went smoothly. The stadium was a nice place to spend an evening. Along the road, we passed a place called Potawatomi Casino Hotel. I’m not much of a gambler, but I do like the atmosphere of casino hotels, there’s usually something else to see or do in addition to gambling. On our drive home from the game, we detoured a little bit more trying to get some night-time photos of the city. It made me sad that there was still so much to see, but we’d be leaving the next day.

Things I learned from this trip:

1.Time to start planning shorter road trips and more time at each location. Lessen the amount of time in the car between cities/hotels. Or both! We were much too tired to only be two days into a road trip.

2.This visit was entirely too short to get a feel for Milwaukee, the next one needs to include a weekend and maybe a few weekdays.

Things I keep in mind when organizing a trip for myself:

Go back for more! There is so much I want to see and do here: stay at the same hotel and visit the Harley Davidson Museum, Visit the water area when it’s warmer, maybe on a weekend, stop in or spend the night at Potawatomi Casino Hotel. Food: I want to try Mader Restaurant! Bar shuttle to the baseball game! That seems like an experience I want to have, and Milwaukee seems to offer lots of options for it.

Some information, such as baseball game information and directions were sought by using ChatGPT or Perplexity.

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