milwaukee skyline on the riverwalk

17 Things to Do in Milwaukee This Memorial Day Weekend: May 26-29 

Check out BikerFest Block Party, Family Kite Festival, Rosé Fest and more.

1. Burlington Jamboree 

ALL WEEKEND | BURLINGTON FESTIVAL PARK 

Perfect for kids and families this Memorial Day Weekend, the Burlington Jamboree features live music, a traveling amusement park, a petting zoo, and more. The four-day event encourages all visitors to “be a kid again.”  

2. Carlos Mencia 

FRIDAY-SUNDAY | MILWAUKEE IMPROV 

Best known for his work in his Comedy Central show Mind of Mencia and The Proud Family, the comedian takes the stage this weekend in Milwaukee for three nights of laughs. Tickets are available online


 

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3. Milwaukee Metal Fest 

FRIDAY-SUNDAY | THE RAVE / EAGLES CLUB 

For fans of moshing music, the Milwaukee Metal Fest is back after a 16-year hiatus. Scream your heart out at the weekend-long festival that will include headliners Lamb of God, Anthrax, and Suicidal Tendencies. 

4. SuperYou 

FRIDAY-SUNDAY | SKYLIGHT MUSIC THEATRE 

This musical inspires audiences to “find the superhero” in themselves. It follows a comic book writer whose superheroine comes to life. The show runs until June 18. Get tickets on Skylight’s website

5. The Zodiac and the Planets 

FRIDAY-SUNDAY | BRADLEY SYMPHONY CENTER 

Take a trip through the stars with the Milwaukee Symphony Orchestra’s performance of The Zodiac and The Planets. The Zodiac, composed by jazz legend Mary Lou Williams, includes 12 movements, one for each astrological sign. 

6. Paper Airplane Day 

FRIDAY FROM 9 A.M.-2 P.M. | DISCOVERY WORLD 

Learn how to make paper airplanes, talk to aviation professionals and fly your paper airplane creations at Discovery World’s Paper Airplane Day. The winner of a distance contest will win 2 free plane tickets from Southwest Airlines.   

7. BikerFest Block Party

SATURDAY FROM 1-10 P.M. | FONDY FARMERS MARKET 

Teaching, supporting and partying is the mission of the BikerFest Block Party. The event hopes to make the motorcycle community more inclusive and provide newcomers with safety gear and job opportunities. Plus, there will be stunt shows and bike races aplenty. Leather not required. 

8. Bring Your Own Art 

SATURDAY FROM 12-2 P.M. | 3536 W. FOND DU LAC AVE. 

Looking to dip into your creative side? The BYOA series aims to make art and create community. Supplies will be provided, but bringing your own materials is encouraged. The event is free and open to all. 

9. Death’s Intern Derrick Book Signing 

SATURDAY FROM 5-7 P.M.  | LION’S TOOTH 

Milwaukee author Becky Franzel and a surprise guest will celebrate the release of her third book at Lion’s Tooth. Death’s Intern Derrick follows Death, Inc. and its employee Derrick as he navigates a PR issue and learns more about the company.  

10. Family Kite Festival 

SATURDAY AND SUNDAY FROM 10 A.M.-6 P.M. | VETERANS PARK 

The 36th year of this kite fest will include kite show performances by professional teams, and the aptly named “Kite Whisperer” will provide free lessons for those starting out. There will also be an opportunity for free kites for the first 100 kids to participate in the Kids Mad Dash.    

Family Kite Festival; Photo by Jason Kopp

11. Oddities and Curiosities Expo 

SATURDAY FROM 10 A.M. – 6 P.M. | WISCONSIN CENTER 

From taxidermy to unusual antiques to bones, you will surely find something bizarre at this event. Vendors and artists from around the country will sell their stock of weird goods – and don’t worry, all of it is legal. Get tickets here

12. East Troy Brewfest 

SUNDAY FROM 3-6 P.M. | EAST TROY VILLAGE SQUARE PARK 

Continue the springtime festivities with a stop at the East Troy Brewfest, which boasts a selection of over 65 beers, ciders and meads from local breweries. The event will also include music, beer pong and t-shirt printing.  

13. Janet Jackson: Together Again Tour 

SUNDAY AT 8 P.M. | AMERICAN FAMILY INSURANCE AMPHITHEATER 

The iconic singer is taking a stop in Milwaukee along her North American tour. Including songs from her 2023 album Discipline, as well as classic hits like “All For You” and “Rhythm Nation,” the show invites young and older fans alike. Plus, the tour features special guest Ludacris.

14. Out There Series 

SUNDAY AT 5 P.M. | DOCTOR’S PARK 

Combining experimental music with nature, the annual Out There Series kicks off this Sunday with performances from three artists. Bring a picnic blanket to the event and get ready to settle in for a unique concert experience.   

15. Rosé Fest 

SUNDAY FROM 11 A.M. – 5 P.M. | STRANGE TOWN 

If you love rosé and a good time, Rosé Fest is an event you won’t want to miss. For those not quite old enough to enjoy the drinks, there will be a bouncy castle and popsicles. And you can test your luck for a chance to win gift cards and gift bags through a raffle

16. Summer Book Swap 

SUNDAY FROM 12 – 3 P.M. | SUPERMOON BEER CO. 

Looking for a great new summer read? Head to Supermoon Beer Co. with a book to trade in for a new favorite. And, you can grab a beer and chat with other book lovers while you’re there.  

17. Memorial Day Water Ski Show 

MONDAY AT 6:45 P.M. | LAKEFRONT PARK 

Celebrate Memorial Day with a waterski performance in Pewaukee. The first show of the season, this performance kicks off another season for the Pewaukee Gators. And catch them this summer every Thursday through Labor Day!


Want more great Milwaukee events? Check out our calendar

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