La Crosse

Why La Crosse: 

A few months ago, I invested in my friend’s real estate fund, Free Heel Capital, which purchased an apartment building in La Crosse. I happened be traveling for Minneapolis, 2.5 hours away, for a work trip. Since I was so close, I knew this was the best opportunity to see the building and to see the town. 

May 5, 2025: Supper Club

After a successful day training in Minneapolis, I started my drive to La Crosse around 14:00. The drive took 2.5 hours. The first two hours consisted of flat nothingness but the final bit of road curved into the Mississippi River Valley and along the river. Soon enough, I crossed the river into Wisconsin and into the surprisingly cute downtown La Crosse. 

The building we purchased is an apartment building right in the center of town. It is probably the nicest apartment building in La Crosse.

Max and Hunter from Free Heel gave me a VIP tour of the building which included going on the roof!

I then checked into my Airbnb just north of downtown. My host was a chill middle-aged lady who moved to La Crosse in college and never left. We watched a little tv and chatted about La Crosse and life. 

At 6:30, Max and Hunter picked me up and we drove north of town along the east bank of the Mississippi River. They explained that La Crosse is the center of a region known as the Driftless – a section of the river that was not glaciated during the last ice age. As a result, the bluffs are taller, steeper and more dramatic and the river is full of floating islands. The islands apparently move around each year. The Driftless is known as a paradise for fishing and fowl hunting and draws visitors from the region. 

We eventually reached a supper club called Sullivan’s. Supper clubs used to exist all over the US but now are concentrated in the upper Midwest. Wisconsin has about 250 supper clubs – the majority located in rural areas. Supper clubs generally have a “cabin” feel with dark wood paneling. Sullivan’s was Irish themed. 

Since it was a nice day, we decided to sit outside and strangely were the only ones.

We ordered Wisconsin old fashioned (made with brandy instead of bourbon), cheese curds, walleye and pork chop. And, as is typical at a supper club, we also got a pass at the salad bar. 

After dinner, we headed back to town to visit a fancy hotel for cocktails. 

May 6, 2025: La Croix

I started the day driving to the top of Grandad Bluff for a sweeping view of La Cross and the Mississippi River Valley. This is by far the prettiest spot I have visited on the river. 

Back in town, I visited the Heileman Brewery. Heileman was the original maker of Old Style Lager, a popular Midwest beer and longtime beer sponsor of the Chicago Cubs. In 1980, Heileman also created the carbonated water brand LaCroix, named after La Crosse. Heileman was acquired in 1996 and brewing/bottling operations for both beverages were moved to other cities. Currently, the brewery is owned by City Brewing Company which brews beer for other breweries on contract. 

Just across the street from the brewery is the World’s Largest Six Pack – painted like a six pack of Old Style. 

Next, I visited La Crosse’s main economic driver: the University of Wisconsin La Crosse.  UWL is a public university with 10,000 students. It was a gorgeous day in the mid-70’s so everybody was out and about. 

I then headed back to downtown for a quick meeting with Max, Hunter and the County. They are doing a great job!

For lunch, we went to a Cajun restaurant recommended by my Airbnb host. 

Then after we went for ice cream nearby. 

I had one hour to kill so I drove to a beach. A beach on the Mississippi River in Wisconsin sounds fake but it is indeed real. 

It was now 14:00 and time to head out. I drove to the tiny La Crosse airport to fly home via Chicago. 

Final Thoughts:

La Crosse is a surprisingly cute small town in a beautiful natural area. It is busy year-round due to the school and the summer tourism season operating countercyclically.  

There is no reason for the average person to visit, but if you live within driving distance and like the outdoors, La Crosse is a hidden gem.