Things to do in Milwaukee Wisconsin

Although I grew up outside of Chicago, I had never been to Milwaukee until a job interview in my mid-20s.  Spoiler, I got the job and lived there for the next six years.  I was surprised to discover how much Milwaukee has to offer considering it’s a mid-size city.  Here are my recommendations on the best of Milwaukee…where to sleep, what to eat, and where to go.

You can visit Milwaukee in any season but I would advise against the winters.  You just never know what you are going to get in a midwest winter.  Since the city is such a manageable size, it’s only a 20-minute ride from the airport to downtown.

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Where to Stay

There are different reasons to choose where to stay.  Usually, it depends on what type of trip I’m planning and looking to spend.  In Milwaukee, I recommend a cool hotel with a great location.

• The Pfister Hotel | The Pfister is a beautifully opulent hotel.  At over 100 years old, they’ve kept the charm but it has all the modern amenities.  It’s in a great downtown location – close to restaurants, theaters and the lake. Bonus, it also has a solid restaurant, Mason Street Grill, in the building.

• The Iron Horse Hotel | The Iron Horse is near the Harley-Davidson Museum (natch) and while its name speaks to the motorcycle enthusiast, there’s no denying it’s just the coolest hotel in the city.  The hotel was created out of a completely renovated mattress factory and it still has a loft vibe.

• Hotel Metro | If you are looking to earn or redeem points (ain’t no shame in that game) then Hotel Metro is where it’s at for your Marriott Bonvoy points.  As part of the Autograph Collection, you’ll have an upscale boutique feel but with corporate amenities.  It’s located directly downtown so you’ll be close to everything!

Where to Caffeinate

What makes a good coffeehouse to me is a place that has a good vibe, good coffee, and good food; the trifecta for me to go back. If not all 3 are in place, it’s not on my list.

• Colectivo | With a few locations in the city, you’re never far from a Colectivo.  Their coffee is great, they have fun seasonal offerings and I’ve never had a bad pastry there.  The Prospect Ave location also has an entertainment venue attached run by The Pabst Theater Group.  

• Stone Creek Coffee | Still very local to Milwaukee, Stone Creek offers fun coffee drinks and a solid offering of baked goods.

• Anodyne Coffee Roasting Co. | Yes they have coffee (it’s good), yes they have pastries but they now (at least in their Bayview location) also serve beer, wine, and pizza. 

Where to Brunch

I prefer this over lunch, you can get something savory or sweet and day drinking is encouraged.

• The Knick | Located inside The Knickerbocker Hotel, The Knick offers up one of the best bloody marys in the city (and the best bloody marys are in the midwest).  Although only offered on Sunday’s the menu is made up of classic American fare.

• Toast | The brunch spot is as cool as the neighborhood it’s located in.  It has a wide variety of fun brunch cocktails, and as someone who loves pancakes, happy to see a few of those options as well.

• Cafe Centraal | One of my go-to brunch spots, Cafe Centraal has a European vibe with a lot of craft beers on tap.  Even their courtyard for outdoor seating is reminiscent of Europe, but the food strikes the perfect balance with American comfort. 

The Dinner Scene

One of life’s simple pleasures is a long leisurely meal with wonderful company and great conversation. 

• 5 O’Clock Steakhouse | This restaurant is a hidden gem in Milwaukee and one of my favorites in the midwest.  It’s a classic supper club, which you can’t find just anywhere, and has amazing food.  My brandy old fashioned sweet recipe is inspired by their version as I think it’s the best I’ve ever had.  

A little to know before you go.  You’ll walk in, sit at the bar, and place your food order as you sip on the cocktail of your choice, I highly recommend the old-fashioned.  When they seat you at your table they will have the quintessential relish tray ready for you to enjoy before your meal comes.  All of those things don’t take away from just how amazing the steak is.  Be warned you probably won’t be able to finish.  Side note, t’s not in the best neighborhood.  Most people park in the lot next to the restaurant but if you choose to take a Lyft maybe stay inside until the car arrives.

• Maxie’s | Located on the outskirts of town, near American Family Field, Maxie’s is worth the trip.  It’s an upscale southern restaurant and I’ve never had a bad meal.  The cocktails are delightful, one of the few places I can get a Pimm’s Cup.  Some of my particular favorite foods there are the fried green tomatoes, ribs, and mac & cheese.  Just know, you probably won’t feel like doing much after dinner.. 

• Botanas Restaurant | You may not know that Milwaukee has a thriving Mexican restaurant scene so I had to include one on the list.  Botanas is what you think of when you want just really good, casual Mexican food.  Sit on the patio, eat the chips and salsa, and drink from the many margarita options to your heart’s content. 

What to do in Milwaukee

Here’s how to fill the time in between eating.

• Milwaukee Public Market | I love a public market and Milwaukee has one of the best!  Filled with local vendors, you can buy cheese, or olive oil, or t-shirts, or spices.  And if you do want to eat or drink, some personal favorites are Thief Wine Bar (get a glass of wine and the Marcona almonds) and St. Paul Fish Company. 

• Lakefront Brewery | Milwaukee is a city known for beer so I have to include at least one brewery on the list. Lakefront is the best when it comes to tours (although you could make a day of it and go to Miller and Sprecher too).  Not only is the technical tour great and you get samples of beer, but they also have a full restaurant where you can stay and dine and continue to enjoy the beer.  A fish fry is something that is a staple in Milwaukee, so if you find yourself there on a Friday, you know what to order. 

• Milwaukee Art Museum | Not only does the Milwaukee Art Museum house one of the largest collections of art in the world, but the building itself is also a piece of art.  It’s right on Lake Michigan and designed by the world-renowned artist Santiago Calatrava.  It’s a key component in the Milwaukee skyline.

• Milwaukee County Zoo | Milwaukee has a great zoo, but it won’t be cheap!  They charge for admission and parking.  If you want to cut down on the budget a bit (or just elevate your food options) you can pack a picnic lunch, but if you choose to dine there they do offer alcohol (it is Milwaukee after all).  There are a ton of animal exhibits and a little train that will take you around the zoo too.

• The Pabst Theater Group | There are three main theaters downtown all owned by The Pabst Theater Group, and they all have a different vibe.  The Riverside is your traditional live theater while the Pabst theater has the grandeur and opulence of days gone by.  Turner Hall is on the opposite side of the spectrum with a little grit.  Depending on what you are looking for, chances are one of the theaters will be able to deliver.

Treat Yo Self

Cocktails or cake (or why not both?), treats are for celebrating every day.

• Leon’s Frozen Custard | In a suburban part of the city, right in front of a Wal-Mart, sits the home to the best frozen custard you will have in your life.  Milwaukee has a few frozen custard spots (love me some Kopp’s too) but Leon’s is the absolute best.  If you’ve had Culvers and you think that is custard, think again.  Real fresh frozen custard is thick and creamy and delicious.  They make it fresh on-site, and although only a few flavors to choose from I’m partial to a sundae.  It doesn’t matter if it’s winter, you will find people lined up outside their walk-up window.  And it’s worth it.

• Von Trier | On the trendy East Side, there is a German bar and cocktail lounge.  They have excellent cocktails but I love to go there for a warm spiked beverage.  IMO, there aren’t enough places that offer a wide variety of warm cocktails.  Von Trier is actually what inspired my spiked apple cider recipe.  While I recommend visiting Milwaukee in the summer if you do go when it’s cold make sure you hit up Von Trier.  Nothing better than coming in from a cold snowy night and warming up with a hot toddy.

• At Random | One of my favorite bars in Milwaukee, and one that holds a lot of memories, is held in an unassuming white building and is called At Random.  Inside you will find a dimly lit bar with a long list of exotic and retro-inspired drinks, cozy tables for two, and u-shaped booths.  I was heartbroken when they closed a few years ago but luckily they were bought. Word has it the new owners are keeping what we all love about the place, check it out and let me know if you love it as much as I do! 

If you will be visiting Milwaukee, Chicago is a short drive away! Check out the what to do in Chicago and a Chicago 3-Day Itinerary.

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