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How the Willy Street Fair Keeps Madison Weird

Posted on September 19, 2024   |   Updated on September 30, 2025
Rob Thomas

Rob Thomas

A man in a white suit waves a bubble wand for a crowd.

Jim Wildeman makes bubbles using his iconic Bubblemobile at the Willy Street Fair. (Emily Mills/Flickr)

It might seem weird to have a summer festival in late September. But Willy Street is a weird place, and darn proud of it. Willy Street, (nobody calls it by its actual name, Williamson Street) has a decades-old reputation as a haven for hippies and rebels, and while the near east side neighborhood may have changed as new residents have moved in, the Willy Street Fair proudly lets that freak flag fly.

Heading to this year’s festival on Saturday and Sunday? Here’s what you need to know:

Origins of the Fair

The fair began in 1978 as a small neighborhood gathering, making it Madison’s longest-running neighborhood fest. It now draws thousands to the 800-1000 blocks of Willy Street as well as the 300 block of N. Brearly. It’s put on by Common Wealth Development and Wil-Mar Neighborhood Center, which offers a food pantry, wellness programs, and much more to the community.

Sounds Good!

Bands will be playing for free on four stages dotted throughout the festival from 2-10 p.m. Saturday and 11 a.m. to 6:30 p.m. Sunday. If that’s not enough tuneage, head to the High Noon Saloon for Willy Street Beats After Dark at 10 p.m. ($25), a four-hour dance party.

Street Shopping

While the music is all free, there will be plenty of food and drink vendors and local artists more than happy to take your money and support the local scene.

Freak Show

The one unmissable event at the Willy Street Fair is the annual parade starting at 11 a.m. Sunday. The funky procession includes costumed revelers, marching bands, hula hoopers, stilt walkers, and more, all led by a converted Cadillac known as the Bubblemobile.

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