Hostel Apostles

Epic Emails: A No-Concerts, No-Sports Milwaukee Weekend!

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So my high school friend Laura is about to embark on her first trip to Milwaukee, Wisconsin, a city that still holds a special place in my heart after having spend nearly 5 five years of my life there. She recently requested that I send her a list of must-dos in town for her and a group of friends that “aren’t really into sports or music.” Although I’m still trying to figure out how someone makes it through life without being really into either of those, she still received a killer – and more than likely overblown – response on things to do during a weekend in the Cream City.


How are you?! My apologies for getting this sent off to you a bit later than expected, but given that your Milwaukee weekend is still a few weeks off, you should have plenty of time to build some of these into your itinerary. Also, this email may or may not have been triggered by the fact that I was at Vesuvio this weekend in North Beach, and yes, it was awesome. Thanks for the tip!
So, although your friends are not necessarily into sports or live music (which unfortunately are 2 things Milwaukee does really well), YOU’RE STILL IN LUCK, because Milwaukee does so many other things awesomely too! To name a few:
  • Drinking on patios in the summer – You asked for it, and Milwaukee delivers in this category. However, my answer will change depending on whether you’re day-drinking or looking for a nighttime patio. If the latter, you will likely find yourself on Water Street at some point, in which case you should check out Trinity, which is a mega-bar that has 3 different Irish pubs joined together, and a big shared patio. Now that I think of it, you could totally hit this during the day too, and its neighbor across the street The Harp actually has a much nicer patio right on the Milwaukee River. For the best day drinking, I highly recommend grabbing Bloody Marys and brunch at either Trocadero, Cafe Hollander, or Benelux. They are owned by the same group and essentially have the same cuisine, but I would pick based on what is closest to where you’ll be hanging out.
  • Speaking of brunch…and restaurants in general… – Milwaukee is a fantastic food town, and predominantly in (but not limited to) the Midwestern sense. The town does burgers and comfort food very well, and even if that’s not your forte, I’d recommend you at least have one order of fried cheese curds while you’re there (it is Wisconsin after all). For burgers, pick either Sobelman’s or AJ Bombers. For creative comfort food, brunch or dinner at Comet Cafe is worth the wait, or the Water Buffalo in the 3rd Ward is a great alternative with patio seating along the river. For a bit of a fancier feel, the Rumpus Room is a solid choice if you’re all whiskey fans, or the Harbor House has good seafood and is right on Lake Michigan.
  • Hit up a brewery tour – …and since you’re from StL I don’t need to tell you to make sure that it shouldn’t be the Miller Tour 🙂 Lakefront Brewery is probably still the best tour in town, but Milwaukee Brewing Co. has been giving it a run for its money lately. You can easily do both in a day (and even throw in Miller for good measure), but I’d make Lakefront the priority, if for no other reason because their Riverwest Stein is one of the best damn ambers on the planet! DON’T leave Milwaukee without trying one, and while you’re at it, make an effort to have at least one Spotted Cow when you’re out at the bars as well.
  • Bryant’s Cocktail Lounge – This bar is so good it’s in its own category. I love this place! It’s my Vesuvio. It’s where I threw my college graduation party. It has over 300 cocktails, but no written menu. It’s off the beaten path (convenient to Milwaukee Brewing Co. though), but worth the cab ride and a great spot to start your night. It’s got this swanky, velvet-walled, 1920’s feel. It’s awesome. Go there! Order a Black Magic. You won’t regret it.
  • The rest of the bars… – If you make it down to Bryant’s, don’t bother walking around there. Hop in a cab to one Milwaukee’s many bar-dense neighborhoods. Cathedral Square is the nice yuppie spot these days, and Whiskey Bar is still the best joint in that area, good for both dancing and strong drinks. Water Street is your standard party block with no shortage of options, but right across the river is Old World 3rd Street, where you’ll find a Hofbrauhaus, a piano bar, and Buckhead Saloon for dancing. Brady Street has a bit more of a laid back vibe, and spots like Jo-Cat’s and Wolski’s are great if you want good beer and metal-tipped darts…these are your typical blue-collar Wisconsin bars! If you’re hanging out with pseudo-hipsters that are still somewhat mainstream, North Ave. is your spot. If you’re hanging out with complete hipsters, head to Riverwest, but only after you call me so that I can guide you to the nicer areas. Wherever you go, all roads often seem to lead to Victor’s at the end of the night, where the metal dance floor, mirrors, disco balls, and carpeting make this place a popular destination for the area’s cougars and cougar hunters.
  • Festivals every weekend – Although the 11-day-long music extravaganza known as Summerfest usually steals the spotlight, Milwaukee is renowned for having a festival virtually every weekend of the summer. Street fairs, concert fests, ethnic festivals…you name it! The weekend I think that you’re there is the Mexican Fiesta, which takes place in the same spot where Summerfest is at a month earlier (Maier Festival Park). I have never been to this particular festival, but if my appropriately-themed experiences at Festa Italiana, Irish Fest, and Polish Fest have been any indication, there will a fare amount of Mexican food and alcohol, likely in the form of margaritas. If you don’t feel like spending an afternoon at a festival, heading to Bradford Beach for some volleyball is another option that will still allow you to enjoy the sunny weather.
  • Art and culture – If I were to only talk about food and booze I’d probably be doing you a disservice. If you’ve got time and you want to peel away from the patios for a bit, the Milwaukee Art Museum is great, and at the very least it’s worth a look from the outside since it’s the town’s architectural landmark. And while I’ve only been to the Harley Museum for events and banquets, it’s a quintessential part of the city’s history and could be worth exploring if it’s convenient.

If you are still hotel-hunting, the Iron Horse (boutique, biker-themed), Pfister (fancy, with BLU bar & lounge and great city views on the 23rd floor), and Astor (basic and traditional, but charming and central) are my go-to’s.

I hope this helps, and I hope it wasn’t an overwhelming amount of information either. Needless to say I get super excited when I hear that someone’s going to Milwaukee and usually go overboard with my descriptions. Regardless, the city is one of America’s best kept secrets, and I’m confident you’ll have a blast regardless of what you do. If there’s anything else I can do to help lemme know. Enjoy your trip, and lemme know the next time you’re rolling through SF! See you out west!



Chris Luecke

Chris Luecke is the Chief Travel Officer at Hostel Apostles and aspiring digital nomad. He lives in San Francisco, California, where he spends his time as a marketer and blogger in the tech and travel industries.

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