An Overnight Trip to Milwaukee

Our stop in Milwaukee was originally just meant to be a quick detour to see our hometown Nationals take on the Brewers on our way from Chicago to Door County, Wisconsin. The plan was simple: catch the game, stay overnight, and move on. What I didn’t anticipate was how much Milwaukee had to offer. Not only did I discover my favorite restaurant of the entire six-day Midwest road trip (Uncle Wolfie’s), but I also loved our hotel, Saint Kate, so much that I asked my husband to get me the lobby’s signature fragrance (sold on their website) as a holiday gift. I left wishing we had carved out an extra day to explore the museums and breweries. Much like our trip to Louisville, Milwaukee completely surprised me. Below is the itinerary from our July visit with our 11- and 8-year-olds.

Practical Takeaways

• Milwaukee is only 90 minutes north of Chicago, making it easy to visit both cities on the same trip with easy flight options. 
• I was naively unaware that Milwaukee is such an arts and culture city, but it’s clear just from the public art everywhere that this is a major draw. If I were to go back, I would plan a trip around seeing shows at the many performing arts centers we kept walking past, such as the Marcus Performing Arts Center or the Pabst Theater. 
• We visited in July and had perfect weather, so this post does not consider the cold winters.

Accommodations

We stayed at the Saint Kate hotel, which quickly became one of my all-time favorites. And yes – the signature scent deserves another mention. I may have slipped a few of the travel-size lotions into my bag just to prolong the experience (thankfully, I can purchase more of the fragrance from afar).

I had originally booked a deluxe room with two queen beds. However, our room wasn’t ready when we arrived and we were upgraded to a Superior King. The space was perfect: a king bed for us and a separate living room with a pullout couch for the kids. No complaints about our room not being ready! The living room even came with a record player, an art table stocked with paper and colored pencils, and a ukulele in the corner with sheet music. Honestly, it took some convincing to pull the kids away from all of this and actually go explore the city.

The Saint Kate isn’t just a hotel – it’s also an art experience. Much like our stay at the 21c Museum Hotel in Louisville, this property features a gallery off the lobby that’s open to the public, along with curated artwork throughout the space and live music in the buzzing bar. Also, its central location made everything easy. It’s directly across from the Marcus Performing Arts Center and within walking distance of restaurants and museums.

Our short list of Milwaukee Activities

American Family Field

Being from the Washington, DC area, we lucked out when we realized the Nationals would be in Milwaukee the same weekend we were planning a trip from Chicago to Door County, WI. It was the perfect excuse to stop at the ballpark. We did exactly what you’re supposed to do there: drink Milwaukee-brewed beer and eat brats. To our relief, no one minded that we were decked out in Nats gear. This is something we could never pull off in certain other stadiums (looking at you, Philly). Then again, that may have been because our team trailed the entire game and practically handed the Brewers the win. Afterward, the kids got to run the bases while I marveled at the engineering of the retractable roof.

SafeHouse

My kids haven’t stopped talking about this spy-themed restaurant. It was easily one of the highlights of our Midwest road trip. The adventure begins before you even get inside: tucked down an alley. An unmarked door sets the tone for what’s to come.

After passing the guard, Moneypenny, in the entryway, we stepped into a space filled with espionage memorabilia. Once we were seated and had ordered our food, the kids were off on a scavenger hunt. It sent them through hidden passageways, down a set of stairs, and through the kitchen. The biggest thrill though was the Magic Bar, where a magician wowed us with mind-bending card tricks and illusions. And yes, beyond the entertainment, the food was surprisingly good, too. 

Uncle Wolfie’s

For breakfast we ate at Uncle Wolfie’s Downtown restaurant. Oh my goodness, it was so tasty. Seriously, we all couldn’t stop stealing my son’s pancakes from his plate. I rarely ever order or eat pancakes, but these were so fluffy and delicious. My daughter and I had the avocado toast and nothing was left on our plates. My husband had the “Wolfundido” – a mix of chorizo, peppers, and potatoes, which was worth traveling back to Milwaukee for alone. It’s no wonder it has been featured in Food and Wine and Michelin. It’s also an easy walk from here to the Milwaukee Art Museum after breakfast, which you may feel is needed after such a hearty meal.

Kohler-Andrae State Park

This beautiful park is an hour north, close to Sheboygan, but is worth noting here as a beach or hiking destination. The boardwalk through the sand dunes provides beautiful views of Lake Michigan. It’s easy to access and has many trails of varying lengths. If we had more time I would also have liked to hike a trail in Lion’s Den Gorge Preserve, which is closer to Milwaukee than Kohler-Andrae.

Helpful Hints

• Spend more time planning a visit here than I did and seek out a food and beer tour to fully appreciate the breweries and brats.
• It was fun to walk along the RiverWalk, where you’ll find the Fonz statue and other public art pieces. Also, on the other side of the river is a bar called 90s2K, with decor that will make any Millennial nostalgic for the Tetris and boy band era.

• Milwaukee is an easy drive from Chicago. Along the way there are some fun stops, including the Mars Cheese Castle, the Home Alone House, and many beaches.
• While walking around downtown, check out the grand lobby of the famous Pfister Hotel. The hotel houses the largest Victorian art collection of any hotel in the world and there is a self-guided tour for visitors.