Top 8 Fun Things to Do in Milwaukee

If you’re asking, “How can I have fun in Milwaukee?” You’re in the right place. Obviously, going skydiving is one of the most fun things to do in Milwaukee. Why? Wisconsin Skydiving Center is a family-friendly dropzone, every day is full of smiles, hugs, high-fives, fist bumps, and huge helpings of confidence-boosting empowerment – all the things that add up to create lifelong memories!  

If you’re here for more than one day (yay!) and searching for unique Milwaukeean activities, we’re just the experts you need! Let’s go on a little tour of our beloved city!

First Things First … Is Milwaukee Wisconsin Worth Visiting? 

ABSOLUTELY! Milwaukee is a hidden gem just waiting to be discovered. Nestled on the western shores of Lake Michigan, our vibrant home offers a blend of rich culture, stunning architecture, and Midwestern charm. The city’s historic neighborhoods boast architectural marvels. Foodies will rejoice in Milwaukee’s culinary scene, where local favorites like cheese curds and custard share the spotlight. Nature lovers will find solace in Milwaukee’s abundant green spaces, from the scenic shores of Lake Michigan to the trails intentionally woven throughout the city. Simply put, Milwaukee has something for everyone, and we can’t wait to host you! 

1. Go Skydiving

What is the best month to visit Milwaukee? Any month that it isn’t snowing – that way you can jump from a perfectly good airplane! Soaring through the sky is the adventure of a lifetime! We could go on and on, but words will never be able to do a skydive justice – you just have to experience it yourself. The sense of freedom, exhilaration, and accomplishment you gain when you jump is unmatched. 

2. Experience the Arts

The Milwaukee Film Festival and Art In Bloom at the Milwaukee Art Museum are two popular events that are anticipated all year long. When springtime encompasses the city, imagine the biggest and best botanical garden exploded all over. If you’re searching for an artsy activity and fun things to do in Milwaukee for couples at night, take your date glass blowing at Square One! 

3. Taste the Brews

On the hunt for things for couples to do in Milwaukee? What about the things to do indoors in Milwaukee? (Rainy days are also a recurring theme here.) Here’s a twofer: our beverage scene! Walker’s Point is one of our most trendy neighborhoods, and is home to the Great Lakes Distillery, Wisconsin’s first distillery since Prohibition! If your opinion is that Milwaukee’s beverage of choice is an icy cold brewski, we’ve got you covered there too. IPA tastings at Lakefront Brewery and a tour through Miller: The Brewery are great options for couples and groups.

4. Music

Music festivals? More lowkey nights? Milwaukee has every type of music lover covered. Milwaukee is known as the City of Festivals! There’s a constant kaleidoscope of colors and a sweet symphony of musical genius that seems to unite the entire city. Our most popular festival, Summerfest, happens in July and is LOADS of fun. If music festivals aren’t your jam (hehe) the intimate atmosphere of Caroline’s Jazz Club is totally worth it.

5. Get Outside 

We think the best way to be outside is with those knees in the breeze two miles up in the sky! BUT, Milwaukee offers a treasure trove of other (way less cool than skydiving) outdoor activities. There’s no shortage of fun things to do in Milwaukee for couples, groups, and families. And the Milwaukee County Zoo in Yankee Hill is a great option for all. Excited chatter from visitors, cheerful chirps of exotic birds, and roars from the world’s most powerful beasts is grounds to create lasting memories with your partner or your crew. For a more self-guided option, take a stroll on part of the Oak Leaf Trail, which spans for over 100 miles. 

6. Enjoy The Water

Clear Water Outdoor is an outfitter for stand up paddleboarding or kayaking on Lake Geneva, Nagawicka Lake, or the Milwaukee River! What is the nicest part of Milwaukee? For us the sky, but we can agree that we have beautiful bodies of water! Enjoying the sparkling and refreshing waters in the heat of summer is ah-mazing and a fantastic option for fun family things to do in Milwaukee. 

7. Stroll Through History 

Go visit Historic Third Ward! Classified as “10 square blocks of O.G. Milwaukee,” the things to do in Historic Third Ward Milwaukee are nearly infinite. Being a warehouse district, the Third Ward is a testament to Milwaukee’s industrious past. The eclectic area seamlessly combined historic charm and modern flair. If you’re looking to explore art galleries, immerse yourself in local theater, and taste some of the best coffee and wine the city has to offer, Third Ward is your spot. Not to be missed is Anodyne Coffee Roasting, which has been serving up the best brews since 1999.

8. Go Brewers! 

Attending a Brewers baseball game offers an electrifying blend of excitement, camaraderie, and joy that makes it undeniably worth it! It’s an easy win to add to your list things to do in Milwaukee with teenagers. Go grab a hot dog, some Cracker Jacks, and an icy lemonade, and watch one of the best MLB teams CRUSH IT. 

We can’t wait for you to experience the beauty of our city in any way you choose but, let’s be real, we’d especially enjoy hosting you for the best Milwaukee activity of all at Wisconsin Skydiving Center! Experience Milwaukee from a whole new angle – book your jump today! Blue skies!