Let me start this article by saying that I really like Madison. Though I personally love Milwaukee far more, Wisconsin’s second-most populous city and its capital is home to some very good friends. I’ve had great times at many of Madison’s character-laden bars, enjoyed wonderful meals at Madison restaurants (including Mint Mark, where I had my single best dining experience of 2024), witnessed some outstanding concerts and comedy shows at Madison venues, and felt a sense of being home away from home 80 miles away in a bizarro version of Milwaukee.
From time to time, work-related things have brought me to Madison. One such occasion happened earlier this month, when I made the short pilgrimage to “Mad Town” to host the second annual installment of our N/A Day “Dry January” Beverage Festival at The Bur Oak. While I made sure to take in some of the local flavor with visits to Madison-specific bars, breweries, and restaurants during my 45 or so hours in town, I thought it might be worthwhile to inject a little more “work” into the work trip with an article idea that loosely ties into Milwaukee.
You might not know this, but with it being Wisconsin’s other “big city”—complete with universities, entertainment and cultural amenities, major employers, and countless tourist destinations—Madison is actually home to a few satellite locations of established (and oh-so-polarizing) restaurant chains that started in Milwaukee. So with that in mind, I decided to see how the Madison locations of those Milwaukee-born chains compared to the ones here.
Café Hollander Hilldale
“Hey, Milwaukee man!” That’s what I heard from a server as I approached the bar at Madison’s first and only Café Hollander, which opened in the Hilldale Shopping Center in 2015. I was thrown off guard. Did my reputation precede me? I mean, Madison does account for more than 4% of our overall readership, so it was possible. Nope! It turned out she just made a safe assumption based on the Bay View Bash shirt I was wearing. Apparently, she used to live in Bay View and work for a Lowlands Group (of which Hollander is part) restaurant in Milwaukee before eventually transferring to Madison. Phew! My cover was safe.
No matter how you feel about Hollander’s food (and you’ll surely tell me in the comments), you can’t dispute the quality of their beer list. There are great Belgian beers and other excellent imports of note, there are specialty Lowlands collaborations with both Wisconsin-based and international breweries, and it’s also one of the only places you can consistently find Lakefront’s Fixed Gear. With that “when in Madison…at a Milwaukee chain” mindset, I ordered a Fixed Gear. Even there in Dane County, the “American red IPA” tasted just as good as it did at the flagship Downer Ave. location in November, when I had two of ’em.
As I waited for my lunch to arrive, I looked around for ways this particular Hollander differed from its Milwaukee-area counterparts. The menu, the beer list, music, and the decor were all very similar to other locations (especially the newer Hollanders, like the one in Brookfield). Really, the only difference I could spot was a clock far in the distance—hence the especially bad photo quality—that showed the time in “MAD” instead of displaying Milwaukee’s (exact same) time.
I ordered a Crispy Chicken Bowl. It was fine, just like pretty much everything I’ve ever had at any Milwaukee-area Hollander. I paid my bill, walked past an L.L. Bean in the shopping complex that seemed reminiscent of Bayshore, drove a few miles away, and checked into my hotel.
Colectivo On The Square
In addition to its dozen cafes in and around Milwaukee and seven in Chicagoland, Colectivo also has three locations in Madison proper. I went to the Colectivo On The Square (25 S. Pinckney St.), which is the oldest of Madison’s Colectivo locations, the closest to my hotel, and literally a block away from my next stop on this admittedly odd adventure.
Immediately upon entering about an hour before closing time, I encountered an Isthmus rack. Apart from that, there weren’t really any Madison-specific differences I spotted during my brief visit. The aesthetic, playlist, decor, drink offerings, and general vibes were all pretty much identical from what I’ve repeatedly encountered at the Bay View, Foundry, Prospect Ave., and Lakefront locations in Milwaukee. Except it’s located across the street from the Wisconsin State Capitol building. My Iced Cold Brew Oat-Chata—its actual name, sorry!—was pretty darn good. I sat for a spell and flipped through an Isthmus, then chugged the rest of my drink because I had another stop to make (two, if you count picking up beer at Young Blood to bring back to my hotel).
BelAir Cantina Madison Square
Since opening its original location on Milwaukee’s east side way back in 2010, BelAir Cantina has been growing and expanding. There are currently seven places in Wisconsin to enjoy the restaurant’s distinct brand of Mexican-fusion cuisine. Of those, five are located within 20 minutes of Milwaukee, the latest to open is in Green Bay, and the sixth one—which opened at 111 Martin Luther King Jr. Blvd back in 2017—is in Madison.
Arriving around 5:30 p.m., I was surprised to see a totally empty dining room. The Madison equivalent of Giannis (Ron Dayne?) would’ve had no problem getting a seat at this location. I took a spot at the bar and took advantage of the $5 house margarita happy hour special as I pondered my dinner order.
I eventually settled on a trio of tacos: one carne asada taco and two pollo verde tacos with a side of rice and pinto beans. The chicken tacos were decent, but as I’m sure you can see from the picture, the steak taco was incredibly dry and disappointing. All things considered, it was okay and the service was actually exceptional. Similar to its standing in Milwaukee, the BelAir in Madison isn’t “the worst” restaurant in the city…but, with all due respect, it was the most disappointing of the weekend.
Oh, and sticking with the whole Milwaukee thing, I ordered a Third Space with my meal.
Cousins Subs
Just to be completely clear, I was NOT setting out to go to every Milwaukee-based chain with a Madison location. For example, I’ve never been to Rare Steakhouse in Milwaukee, so I didn’t really have a point of comparison. Same goes for Red Rock Saloon, which I went to, like, once 10 years ago. Still, I felt my Milwaukee-tinged Madison mastication mission was missing something. Then it hit me: a vendor at N/A Day mentioned getting lunch at a nearby Cousins Subs before setting up for the event. “WAIT, COUSINS STARTED IN MILWAUKEE!” I quietly thought.
So on my way out of town, I went a few minutes out of my way to stop at the the Cousins at 3715 E. Washington Ave. It’s also the only Cousins location in Madison, which is kind of surprising, right? Anyway, I showed up shortly after it opened and, strangely, I wasn’t the first person there.
Lately, I’ve been in a Chicken Bacon Cheddar Cheese Steak pattern, but since I was in foreign territory, I decided to go for a literal “Classic” from the Cousins menu. Have I had better Pepperoni Melts? Sure. Have I eaten worse Pepperoni Melts? Absolutely. I put this one in the 70th percentile of all-time Pepperoni Melts.
MADISON LOCATIONS OF MILWAUKEE-BASED RESTAURANT CHAINS: You’ve had better and you’ve had worse, but they each serve a purpose. Sometimes they’re spacious and have a large menu. Sometimes they do a decent job and have a great location. Sometimes they’re literally just a Cousins near the highway out of town. If you live in Madison (or somewhere that’s not Milwaukee), go for any or all of these! If you live in Milwaukee and you’re visiting Madison, you should probably live a little and enjoy the wealth of amazing local options at your disposal in Wisconsin’s second-best city.
Epilogue
I owed Madison one (at least) after spending most of the weekend at Milwaukee-based establishments. So the least I could do was go to Rocky Rococo on Sunday afternoon when I returned home.
I got a Sausage & Pepperoni Super Slice. Even though it was the only Super Slice option available to me, it ruled. Doughy, salty, cheesy, and delightful! Long live Madison. Long live Milwaukee. Long live YOU.