City Cast Madison logo

Your Guide to May 2026 in Madison

Posted on April 30   |   Updated on June 4
Rob Thomas

Rob Thomas

A man in a gray shirt in front of a blue brick wall.

Wisconsin comedian Charlie Berens sold out three shows at Overture Hall in May, and is on his way to selling out the fourth (Overture Center)

Happy May! While UW-Madison commencement is the big event this month, there's plenty going on for townies and students alike. Here's your guide to the events you shouldn't miss.

😆 Charlie Berens Gets a Wisconsin Welcome

How popular is Wisconsin comedian Charlie Berens? He’s sold out three of his four shows at Overture Hall on May 8 and 9 – only a few seats for the late show on May 8 remain. Listen to him on the City Cast Madison podcast talk about what makes Wisconsin funny, and his surprisingly serious stance against data centers.

📰 Extra! Extra! Newsies Hit Madison!

Children’s Theater of Madison is putting on the hit Broadway musical about a group of ragtag newspaper boys who rally against their greedy publishers May 2 through 17 in the Starlight Theater at MYArts.

🎉 The Center for Black Excellence’s Grand Opening

Madison’s long-awaited Center for Black Excellence and Culture will open its doors on May 6, with a free grand opening celebration and open house, so you can explore all three levels of this testament to Black resilience and creativity.

📚 Jane Smiley Brings Back ‘Lidie’

Former Wisconsin author Jane Smiley (“A Thousand Acres”) will close out the Wisconsin Book Festival’s spring series with a free May 6 event at Madison Central Library to talk about her new book “Lidie,” which revisits the main character from her 1998 novel “The All-True Travels and Adventures of Lidie Newton.”

People walk under a large yellow banner in a park.

Brat Fest brings thousands to Willow Island on Memorial Day Weekend. (Corey Coyle / Wikimedia Commons)

🌭 Brat Fest Cuts the Mustard

It’s three days of food, music, and fun at Brat Fest on Memorial Day Weekend, May 22 through 24 on Willow Island at Alliant Energy Center. Headliners for the music stages include The Lovin’ Spoonful and Great White.

🎸 Courtney Barnett is Back!

Acclaimed indie-rock singer-songwriter Courtney Barnett took a few years off, but she’s back with a new album and tour. She’s playing The Sylvee on May 15.

🌷 Tiptoe Through the Tulips

Parrfection Produce Farm Market near Monticello is hosting its Tulip Fest 2026 on May 8. There’ll be over 100,000 tulips (minus any that the deer get into), plus food trucks, bouncy houses, and opportunities for lots of beautiful photos.

Share article

Hey Madison

Sign up for your free daily toolkit to get the most of the city you love.

Can't subscribe? Turn off your ad blocker and try again.

Madison's Best

See All
Madison's BestJune 10

How to Celebrate Pride Month 2026 in Madison

The city’s biggest LGBTQ+ gathering, OutReach Magic Pride Festival, isn’t actually until August, but there are still plenty of ways to ce...

A group of 6 people sit on a bench smiling, looking on at the Middleton Pride Festival
Madison's BestJune 3

Your Guide to Frank Lloyd Wright's Madison

Legendary designer Frank Lloyd Wright called Madison home and he left his mark on the city. Here's some of his most famous buildings, fro...

A building with glass windows and a triangular roof.
Madison's BestJune 2

Your Guide to June 2026 in Madison

If you’re looking for a page-turner to take to the beach this summer, UW-Madison graduate Joseph Eckert is coming back to town to Lake Ci...

A group of people at tables in front of a marble building.
Madison's BestJune 1

How Madison’s Capital City Theatre is Reinventing ‘RENT’

Madison's Capital City Theatre is putting on a bold new version of the Tony-winning musical 'RENT' at the Orpheum Theater June 5-7. For i...

A woman gestures to several other people in a room.
Madison's BestMay 12

Wisconsin Authors Are an Open Book on New Podcast

On the new podcast "Writing Forward," Madison writer Jeff Oloizia interviews Wisconsin authors about their writing process, how to be suc...

A man in a blue shirt stands next to a shelf of books.
Madison's BestApril 29

The Madison Mystery Tour Is Coming To Take You Away

Over a half-century after they broke up, the Beatles still have a huge hold on popular culture. For over a decade, the Madison Mystery To...

A man in a bow tie plays an electric guitar behind a man playing a keyboard.
Madison's BestApril 27

Madison’s Circus Scene isn’t Clowning Around

While Circus World in Baraboo is what put Wisconsin's circus scene on the map, there's lots of acrobatics, clowning and more going on in...

A man and a woman in a circus ring juggling hoops.
Madison's BestApril 21

Your Guide to the Barrymore Theatre’s Fit Film Fests

In addition to being a favorite spot for live music and comedy, the Barrymore Theatre on Madison's east side hosts one-night-only film fe...

The interior of a theater full of people.

The latest in Madison

Food & DrinkJune 11

Where to Watch the World Cup in Madison

The 2026 FIFA World Cup tournament kicks off today, and Madison soccer fans are ready. Here's where to watch the matches, including bars...

A man in purple cheers surrounded by fans in bleachers.
Food & DrinkMay 28

Madison's Best New Restaurants

This month's list of new restaurants include a new coffee shop on Winnebago Street, an ice cream shop coming to downtown Sun Prairie and...

A building with an orange outline of two palm trees on the side.
Madison, ExplainedMay 18

How Smart Studios Put Madison on the Musical Map

Why did Nirvana, Smashing Pumpkins, Death Cab for Cutie and other bands want to record songs in Madison? As a new documentary explains, S...

A two-story red brick building on a street.
Food & DrinkMay 14

These Madison Butcher Shops Are a Cut Above

With summer coming up, you might want to stock up for the next cookout. Here are some of Madison's favorite butcher shops, from Meat Peop...

A man in glasses peers at a stack of hamburger patties.
Food & DrinkMay 7

Supper Clubs in Madison You Have To Try

You can savor the Wisconsin supper club tradition without traveling far from Madison, hitting historic spots like Tornado Steak House, Ka...

A photo of a plate of food and a nighttime photo of the exterior of a restaurant.
Madison, ExplainedMay 4

Quiz: Are you a True Madisonian?

You may live in Madison, but are you a true Madisonian?

A downtown street scene with a capitol dome at the top of the street.
Food & DrinkApril 16

Madison’s Favorite Neighborhood Bars

Madison has its share of high-end cocktail bars, but there's nothing like a neighborhood bar where it feels like everybody knows your nam...

The exterior of a bar with brick and red wood.
Madison HistoryApril 15

The History of Madison in 10 Isthmus Headlines

Madison alt-weekly Isthmus is celebrating its 50th anniversary this month. The editors dug through the archives to look to see how the ne...

A black-and-white photo of two men surrounded by newspapers.