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Your Guide to September 2025 in Madison

Posted on September 2, 2025   |   Updated on September 30, 2025
Rob Thomas

Rob Thomas

Cyclists coming down a ramp with people watching along the sides.

Ironman athletes love the crowds at Ironman Wisconsin, which returns Sept 7. (Matt Schilder / Flickr)




All you autumn lovers who have been waiting for August to end can rejoice! It’s September, and while it may not feel much like fall right now, I promise by the end of the month you’ll be wearing your flannel and sipping on cider. On the City Cast Madison podcast today, the team talks about what we’re most looking forward to doing, seeing, and eating this month.

Here are a few more things going on in Madison to make it a September to remember!

🎽 I Am Ironman!

For triathletes, Ironman Wisconsin is a very special event. Not only is the event itself pretty unique among Ironman competitions because of its location, but the city really comes out to support the athletes.

This year’s Ironman takes place on Sept. 7. Athletes will take a two-lap swim in Lake Monona, a bike ride through the scenic rural countryside, and a punishing run around campus and through downtown. There are events planned Sept. 4-8 at Monona Terrace, as well as an “Ironkids” fun run on Sept. 6. Good luck, athletes!

🛍️ Meet Me on Monroe Street

One of my favorite September festivals is the Monroe Street Festival on Sept. 13, where businesses up and down the west side thoroughfare participating. Grab a slice at Pizza Brutta, pick up some vinyl bargains at Strictly Discs, take part in the community scavenger hunt, and enjoy live music, a bouncy castle for the kids, and other goodies. It’s a festival that’s as eclectic as the street it's on.

🎭 The Play’s the Thing

September is the time when many local theater companies launch their seasons, and there are some strong lineups this month.

Forward Theater launches its 2025-26 season in the Overture Center Playhouse with Eboni Booth’s “Primary Trust” (Sept. 4-21), a comedy about an ordinary man forced by economic circumstances to reinvent himself.

The Bartell Theater is presenting a pair of productions that provide contemporary spins on classic theater. William Shakespeare’s “Hamlet” (Sept. 19-Oct. 4) is reimagined as a tale of addiction, with its protagonist recounting his tragedy at an AA meeting. And “An Ideal Husband” (Sept. 26-Oct. 11) transports Oscar Wilde’s comedy to the backstabbing world of “The Real Housewives of D.C.”

University Theatre will bring back its well-received summer production of “Dance Nation”(Sept. 11-21), which is about the cutthroat world of preteen competitive dance.

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