The 14 Best Things To Do in One of the Midwest's Most Underrated Cities

Known by the nicknames the Good Land and the City of Champions—and abbreviated as MKE—Milwaukee, Wisconsin is an underrated vacation. This is especially true if you’re someone looking for a walkable city with some free transit options and an abundance of breweries, bars and restaurants.

Milwaukee is located about an hour and a half north of Chicago and—just like the Windy City—also sits on the coast of Lake Michigan. The City of Champions has a riverwalk and rivers that connect to Lake Michigan as well. But MKE has its own unique vibe and personality, which means there are plenty of fun things to do—whether you're planning a weekend trip, looking for something to do today or scheduling a longer stay within an upcoming road trip with friends.

I just returned from spending a few days in Milwaukee, WI, and have plenty of recommendations to share from my amazing getaway. So, if you’re looking for a new place to visit this year, take a look at the 14 best things to do in Milwaukee to see what this Midwestern city has to offer.

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Best Things To Do in Milwaukee

1. Milwaukee Public Market

Part market, part eatery, the Milwaukee Public Market is an indoor block of food stalls, bars and shops. You can get sushi, fresh fish, Bloody Marys, artsy cupcakes and much more. It can be really crowded, but the range of food offered is worth checking out.

The market is located in the Historic Third Ward, so if you don’t find something you want to eat inside here, you can head outside and walk around to one of the many other restaurants in the area.

2. New Barons Brewing Cooperative

Located south of the city’s downtown, in a more industrial, spread-out part of town called Bay View, is New Barons Brewing Cooperative. It’s Wisconsin’s first co-op brewery and patrons can become member-owners of the brewery, which gives them a say in what they brew and they receive their first beer free every day when visiting the taproom—for life.

But if you’re like me and just want to pop in for some beer and to check out the vibes, that’s more than welcome, too. The night I went, the brewery was hosting a special night with live music, which added a lot of fun to the evening.

3. Afternoon Tea at The Pfister

The Pfister Hotel in Milwaukee offers an Afternoon Tea, which is a lovely high tea experience. It takes place in the hotel’s Blu cocktail lounge and is complete with a "Tea Butler" and all. You definitely feel like you’re transported back in time to when the Pfister first opened in 1893.

You get a tower of delectable tea treats (tiny sandwiches, gorgeous cookies, tarts and more) and each person gets to pick their own blend of tea. During the experience, the Tea Butler gives you an in-depth explanation of all the tea blends they have, which are from Rishi Teas (a Milwaukee-based company). Then, you can make your own blend with special additions like fresh ginger, fruit, mint, cinnamon sticks and more.

Afternoon Tea at The Pfister is truly an elegant experience with a lovely view of the lake side of the city. It happens on Thursdays–Sundays, with seating times at 12:00, 12:30, 1:00, 1:30 and 2:00. You can make a reservation on their site; it costs $68 for adults and $32 for children.

4. Take the HOP Streetcar System

I truly love any city that has free transit, and The HOP streetcar system in Milwaukee is just that. If you thought only San Francisco had streetcars, you’d be wrong; The HOP is a sleek, modern streetcar that has two routes through the downtown area of Milwaukee. There was a stop that was a five-minute walk from The Pfister (where I was staying) and it was able to take us to the lakefront, near the Milwaukee Art Museum (more on that later) and the Historic Third Ward.

While it doesn’t span a huge area of Milwaukee, it does get to all the tourist spots in the downtown area, and that beats walking sometimes. It’s also easy to track with an app or their easy-to-read schedule and map (from our experience it was always pretty punctual).

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Fun Things To Do in Milwaukee

5. Amped Karaoke Private Karaoke

If you like karaoke and want to sing your heart out with all your friends, Amped Karaoke is such a fun place to do that. The rooms are modern and they have a nice touchscreen system that allows you to queue songs easily. While they don’t have songs from the last year or so, I was able to find hits from Grease, Bad Bunny, Selena, High School Musical and more (basically, any classic karaoke song should be available).

Their drink menu is also amazing if you drink alcohol, with all the cocktails and shots named after iconic songs. I ordered the Honey Honey (an ABBA song), which had Jack Daniel’s Tennessee Honey, Sweet Vermouth, a cinnamon stick and club soda in it, and my partner ordered Cherry Pie (a Warrant song), which had Maker’s Mark Bourbon, Cherry Syrup, Lime Juice and Lemon-Lime Soda in it. Both of the cocktails came in little disco ball cups we were able to take home. We also had the Cake by the Ocean (a DNCE song) shot, which was made with vanilla vodka, strawberry simple, whipped cream and sprinkles. Lots of sweet flavors, I can tell you that much!

It's also pretty affordable, with Standard Karaoke Suites (two to nine people) and Large Karaoke Suites (10 to 16 people) costing $12 per person, per hour. Their Premier Karaoke Suite (for more than 17 people) costs $17 per person, per hour. All suites have a 2-hour minimum.

6. Street Fairs and Timely Fests (Festa Italiana, Beer Fest)

Like many lively cities, Milwaukee has great street fests, fairs and seasonal events. While we were there at the end of May, we were able to attend Festa Italiana—which was a major celebration of Italian culture with food, music and more hosted by the Italian Community Center of Milwaukee—and the Wisconsin Beer Lovers Festival, which was put on by the Wisconsin Brewers Guild and featured tasting from tons of local breweries.

If you want to see what events are going on while you’re visiting Milwaukee, check out their website. They also call themselves the City of Festivals, so you can check out that part of their site too, for yearly fests.

7. This Is It Bar

If you’re looking for a fun night out and don’t want to go to a club, This Is It is it. This Is It is a gay bar that’s been open since 1968 and is currently co-owned by world-famous drag queen, Trixie Mattel (who’s from Milwaukee, WI) and George Schneider. It’s the oldest gay bar in Wisconsin and the vibes are immaculate.

The drinks were great and so affordable, plus everything is a double, according to a bartender we spoke to. There was so much joy around us and the music was great as well. It definitely looks and feels like a neighborhood bar, but no frills are needed when you’re out to have a great, queer time. There was also a group of straight people there having a fun time; it was truly a welcoming space for all. We wish we’d seen a drag show there, but maybe next time.

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Things To Do in Milwaukee With Kids

8. Milwaukee Brewers Game

We attended a Milwaukee Brewers vs. Chicago Cubs game while in town, and the Brewers stadium, American Family Field, is such a nice ballpark. The parking situation is a bit time-consuming, but we’re used to taking the train to Wrigley Field in Chicago, which we didn’t realize spoiled us a bit.

It’s a nice, newer stadium with a retractable roof for rainy games. There was a lot of interaction with the kids in the audience—plus, their mascot, Bernie Brewer, has his own slide that kids will get a kick out of. It’s definitely a pretty family-friendly atmosphere, but most baseball games usually are (from my experience). Who doesn’t love sharing America’s favorite pastime with their kids?

9. Milwaukee County Zoo

Most zoos are great places for kids, and the Milwaukee County Zoo is no different. Located 20 minutes or so from downtown Milwaukee, the Milwaukee County Zoo has a lot of immersive and fun exhibits and activities for kids. They also have a ton of “rides,” from a carousel to the Sky Safari, which is a ski lift that goes around the park.

Admission ranges from $15 to $18 if you’re a county resident and $16.75 to $19.75 if you’re not a resident. Parking is $15.

10. Walk Along the Milwaukee River and See the City

This is an activity that you can do if you don’t have children, but it’s nice to have some free options if you do have kids.

You can take your kids and walk along the Milwaukee River in the downtown area. The RiverWalk district of the city was established in the early 1990s and now features boardwalks and trails all along the river. The RiverWalk connects three downtown neighborhoods with 20 blocks of “pedestrian promenade.”

You can watch them raise and lower the bridges for boats that pass and look at the pretty city lights. There are also a lot of nice restaurants and shops along different spots of the RiverWalk if you do want to splurge a little.

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Things To Do in Milwaukee Over 50

11. Colectivo Coffee Lakefront

If you want to enjoy some yummy coffee and breakfast burritos while also getting a gorgeous outdoor spot to relax, the Lakefront location of Colectivo Coffee in Milwaukee is the perfect place for you. While anyone can enjoy this little cafe spot, there were a lot of people over 50 meeting up with friends or in groups, enjoying the nice outdoor seating area they have set up.

12. Milwaukee Art Museum

Back to the Milwaukee Art Museum—if you’re interested in an art museum with a simple layout, not a lot of stairs and a lot of natural light, then this place is for you. The outside of the museum is enough to stare at for a long time; the Burke Brise Soleil on the outside of the museum is a moveable sunscreen that looks like wings that can open and close. You can watch them open when the museum opens, “flap” at noon and close back up at 10 p.m. This was all designed by Spanish architect Santiago Calatrava and opened in 2001.

And once inside, the museum has more than 30,000 works and has almost 400,000 visitors every year. Some famous artists that have pieces in the Milwaukee Art Museum include Georgia O’Keefe (they have one of the largest collections of her work and she’s a Wisconsin native), Andy Warhol, Claude Monet and Roy Lichtenstein. Again, the natural light and setup make this an enjoyable museum to walk through.

13. Stay at The Pfister, Eat at The Cafe

We’ve mentioned The Pfister a bit already, but if you want to splurge and love historic hotels that look like they did when they opened, then The Pfister is for you. 

There is a wide range of people who stay here, not just people over 50, but this is definitely a lovely place for a more mature couple to stay.

It’s in a great location in the downtown area, the rooms are gorgeous and it has a Cafe on site if you want to have a decked-out breakfast. You even get a complimentary glass of champagne when you check in if you’d like, which just screams luxury.

14. Mason Street Grill for Lunch

Attached to The Pfister is Mason Street Grill, though it’s not fully affiliated with the hotel. It’s reminiscent of a jazz club or a fancy 1940s cocktail bar, with plush leather seats, a fancy bar and a laidback vibe.

We enjoyed brunch here on a Sunday morning, and it’s also one of Milwaukee’s top restaurants, so I’d be interested to see how dinner feels here too. Regardless of what time of day you come in, you’ll definitely get a fancy meal. 

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