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Your Guide to May 2025 in Madison

Posted on May 1, 2025   |   Updated on September 30, 2025
Rob Thomas

Rob Thomas

A baseball player in a gold uniform swings at a pitch.

The Madison Mallards throw their first pitch of their 25th anniversary season on Memorial Day. (Mallards Baseball / Flickr)

It’s May! A time of transition in Madison, as the warm weather is enticing people to hang out outside, and as graduating UW-Madison students transition into their post-college lives. On the City Cast Madison podcast today, host Bianca Martin, producer Jade Iseri-Ramos, and I talked about the things we’re most looking forward to doing, seeing, and eating this month.

City Cast

Your Guide to May 2025 in Madison

00:00:00

Here’s some more fun stuff to do in Madison this month.

Drinks are a Breese

Breese Stevens Field is hosting two events for imbibers this month. First off is Uncork Me Wisconsin, a May 10 event that celebrates the best wines, meads and ciders made right here in the Badger State. A $65-$75 ticket gets you several hours of unlimited samples from over 30 Wisconsin wineries and cider houses, and there’s live music, a drag show, and food trucks as well.

And May 31 brings the return of Distill America, sponsored by the Madison Malt Society. An $75-$90 ticket gives you the chance to sample spirits from 90 different producers from across the United States, including some bottles that haven’t even been publicly released yet.

Wide World of Madison Sports

Speaking of Breese Stevens, it is an athletic field, after all, and sports are coming back in May. The Madison Radicals start their 13th season as the city’s Ultimate team on May 17 with a match hosting the Pittsburgh Thunderbirds.

And the Madison Mallards will kick off their 25th anniversary season on Memorial Day at the Warner Park Duck Pond with a game against Fond du Lac. The Mallards revel in special promotions, giveaways, and other goodies, so expect them to pull out all the stops for their Silver Anniversary.

A Busy May at The Sylvee

May can be a quiet month on Madison’s live concert scene, as spring tours are winding down and summer tours have yet to get rolling. Both the Barrymore Theatre and the Orpheum Theater are pretty much dark for the month.

But The Sylvee has a lot going on in May. Shows by Amyl & The Sniffers (May 9), Sierra Ferrell (May 16), and Rainbow Kitten Surprise (May 17) are already sold out. But you can still get tickets to see the spiky rock of Beach Bunny (May 3) and Sharon Van Etten with her new band The Attachment Theory (May 8), and the sunny pop rock of Saint Motel (May 11).

“Hello, Jerry.”

Madison gets a double dose of Jerrys (Jerries?) at Overture Hall at the end of the month. First on May 29, the Jerry Ensemble Cabaret in Promenade Hall features top student performers from Wisconsin high schools performing a night of showstopping tunes.

Then the following night, on May 30, comedian Jerry Seinfeld performs two shows in Overture Hall. As has been reported, top tickets are going for $800 a pop, but there are still some tickets available in the cheap seats for $70-$90.

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