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Entertainment: Cinco de Mayo Collides With Fastest Two Minutes in Sports » Urban Milwaukee

Story Center by Story Center
April 30, 2026
Reading Time: 4 mins read
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2014 Kentucky Derby. Photo by Bill Brine, CC BY 2.0 , via Wikimedia Commons

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Kentucky Derby. Photo by Bill Brine, (CC BY 2.0), via Wikimedia Commons

We got more than our fair share of April showers, so hopefully we can expect plenty of May flowers. One thing is for certain – May will bring plenty of events to check out in Milwaukee. This weekend you can raise money for cancer charities while playing board games at the Gaming Hoopla and get inspired for your big day at the Wisconsin Bridal & Wedding Expo. Bust out your big hats and extravagant outfits for the Kentucky Derby Day at Saint Kate and celebrate Cinco de Mayo at one of Milwaukee’s longest-running festivals.

May 1-3: Gaming Hoopla

Raise money to help fight cancer while also playing your favorite tabletop games at the Gaming Hoopla. The Baird Center will host the event, which will host board games, card games, roleplaying games and more as well as hundreds of scheduled events like tournaments and silent auctions. Guests can also check out the open gaming areas and participate in raffles, all while raising money for cancer charities. For more information, visit the Gaming Hoopla website.

May 2: Cinco de Mayo Festival

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Join UMOS and the El Conquistador Latino Newspaper in celebrating Cinco de Mayo at one of Milwaukee’s longest-running festivals. The Cinco de Mayo Festival will bring Mexican food, live music and dance, taco trucks and more outside of the UMOS corporate headquarters. Cheer on your favorite pup at the Chihuahua Beauty Contest or try your hand (and stomach) at the Tamale Eating Contest. The festival also promises a carnival, a car show and much, much more. The event is free to attend and will run from 11 a.m. to 7 p.m.

May 2: Kentucky Derby Day at Saint Kate

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Saint Kate The Arts Hotel is teaming up with Woodford Reserve to throw a free Kentucky Derby Party. The hotel will have the races streaming on a giant projector screen while guests try Derby-inspired foods, enjoy specialty cocktails like the Mint Julep and participate in raffles. Don’t forget to dress the part, as the event will also host Best Dressed and Best Hat contests. The event will begin at 1 p.m. To RSVP, visit the Saint Kate website.

May 3: Schlitz Audubon May Market

Over a dozen local vendors will set up shop at the Schlitz Audubon Nature Center for the May Market. Local vendors will sell wares such as pottery, jewelry, art and more. The center will also grant full access to its trails, so guests can shop and then explore. The event will also offer free wine samples and additional beverages and snacks for purchase. For more information, visit the Schlitz Audubon Nature Center’s website.

May 3: Wisconsin Bridal & Wedding Expo

Wedding planning is tough, but thankfully, the Wisconsin Bridal & Wedding Expo is here to make things a little easier. Guests can get inspired for all aspects of their special day, from sampling caterers to meeting the perfect wedding planner. Guests can try out photo booths, get dolled up by makeup professionals at the Glam Bar and win prizes. The Wisconsin Bridal & Wedding Expo will run from 1 p.m. to 5 p.m. at the Baird Center. For more information, visit the event’s website.

May 3: David Byrne at Miller High Life Theatre

Whether or not you caught the annual showing of Stop Making Sense at the Milwaukee Film Fest last month, you can never have too much David Byrne in your life. Thankfully, the Talking Heads frontman is performing in Milwaukee for the first time in eight years. Byrne will perform at the Miller High Life Theatre in support of his latest album Who Is the Sky? The show will begin at 8 p.m. For more information and to purchase tickets, visit the Pabst Theater Group’s website.

‘ The preceding article may include information circulated by third parties ’

‘ Some details of this article were extracted from the following source urbanmilwaukee.com ’

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