Milwaukee in the Fall: A Perfect 4-Day Midwest Getaway
For Minnesotans, the coveted four-day MEA weekend in mid-October is a perfect excuse for a fall road trip. And at about 5½ hours from the Twin Cities, Milwaukee makes a great long-weekend destination.
We spent an MEA weekend there several years ago, and it exceeded our expectations. I had been to Milwaukee many times for work and conferences but had never really had the chance to settle in and experience the city for more than a day.
I really enjoy MKE. It’s diverse and vibrant, with a working-class ethos and a wonderful setting along Lake Michigan and the Milwaukee River. I’ve described it as “Chicago without all the people”—although perhaps Chicago is really Milwaukee with more people. Either way, for travelers like us who appreciate a little less congestion, Milwaukee hits a sweet spot.
Oh, and did I mention how great the people are?
We do have a lot of friends in Brew City, and I’d be remiss not to give them a shout-out and thanks for many of these recommendations.
Here’s the 4-day itinerary:
Day 1: Minneapolis → Holy Hill → Milwaukee
This day offers a scenic stop on the long drive to Milwaukee, a classic MKE food stop, and stay in the historic and iconic Pabst brewing area.
Drive from Minneapolis
Stop for views at Holy Hill Basilica + Scenic Tower
Continue into Milwaukee and stop at Kopp’s Frozen Custard for a burger & custard
Check into Airbnb at Malt House / former Pabst Brewery
Walk around the old Pabst complex. Notice the history exhibits.
Casual first evening: San Giorgio Pizzeria Napoletana or Calderone Club next door (Milwaukee thin-crust style)
Night cap at Stella’s: A Cocktail Dive.
Day 2: Milwaukee Architecture, Art + Lakefront
This day has some great architecture, museums, and wonderful strolls on the lakefront and Riverwalk.
Comet Café for breakfast/brunch
Milwaukee Art Museum
Walk the lakefront, check out Pier Wisconsin area
Wander around the Historic Third Ward
Stroll through the Milwaukee Public Market
RiverWalk- take a selfie with the bronze Fonzie
Milwaukee City Hall- quick pop in to see the wonderful atrium
Saint Kate Arts Hotel galleries – another quick pop-in
Lakefront Brewery: If you are going to do a brewery tour, do this one.
Drinks on the Journeyman Hotel rooftop for sunset.
Dinner at TreRivali or Onesto
Day 3: Harley-Davidson, Bronzeville, Walker’s Point
Even if you aren’t a motorcycle enthusiast, you will appreciate the history and design behind the iconic Harley-Davidson brand. You will explore two neighborhoods, Bronzeville and Walker’s Point. Car is needed for this day.
Harley-Davidson Museum - spend several hours here.
Lunch at Sherman Phoenix Marketplace
Head to Bronzeville for America’s Black Holocaust Museum
Walk along King Drive to see the public art
Stop at Indeed Brewery for afternoon drink
Dinner at La Dama or somewhere in/near Walker’s Point
OR visit the Boerner Botanical Gardens China Lights Wisconsin display.
Day 4: Breakfast + The Domes before heading home
Grab breakfast, browse the stop at the unique Mitchell Park Domes before heading home.
Tupelo Honey Southern Kitchen & Bar
Mitchell Park Domes
Head home and stop somewhere before crossing the border to pick up your New Glarus beer (which can’t be sold in MN).
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Here's a bit more detail on some of the spots we're recommending:
Holy Hill Panorama Viewpoint
A pit-stop on the way from Minneapolis to Milwaukee that deserves time (especially in the fall) is the Basilica of Holy Hill. Located 35 miles northwest of Milwaukee, this is a very popular spot in the fall and for good reason. Situated atop a hill, the Basilica has a Scenic Tower that can be climbed to get an awe-inspiring panoramic view of the Kettle Moraine area. Hope for a blue sky day like we were lucky to have!
Pabst Malt House AirBNB
In a city known for beer, what better place to stay than an historic former brewery building? Our Airbnb was in the Malt House, connected to the old Pabst Brewery sign. The adaptive reuse had many nods to its brewing past and a large atrium. We loved the convenient location and the ability to walk to most things within the city.
Milwaukee Art Museum
This museum is an architectural gem. The original War Memorial Center (1957) was designed by Eero Saarinen. The Quadracci Pavilion (2001) by Santiago Calatra features the iconic Burke Brise Soleil- moveable wings that unfold and fold daily. And HGA did the East End addition in 2015. Oh, and there is some art there too.
Harley-Davidson Museum
Another building that HGA had a hand in, the Harley David-Museum is another iconic must-see. Even if you aren't a Hog-loving rider, this museum is a master class in brand. Make sure to see the impressive collection space--- ideally on a guided tour, where they will tell some of the fascinating stories around the history of HD and the collection.
Stella's: A Cocktail Dive
This classic dive bar has a quirky nightly happy hour from 9:00 to 9:15 pm featuring $1 drinks. Yes, you read that correctly!
Boerner Botanical Garden- China Lights Wisconsin
The county botanical garden features a light, music and cultural festival in September and October. Stroll through the gardens and enjoy the impressive displays of light and color.
Brew City: Beer is likely the thing that Milwaukee is most famous for. Whether it's the classics like Schlitz, Miller or Pabst, or one of the newer breweries, make sure to check out some of the history as well as some samples!
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