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Year in and year out, people across the country go crazy for March Madness. This year Downtown Waukesha is getting involved again with Main Street Madness. Every Monday – Thursday starting in March, head over to the Downtown Waukesha Facebook or Instagram page to vote for your favorite Downtown Waukesha experience!

As the winners are announced, we’ll update this page so check back often! Bracket will be released soon, check back to see who is up to win the crown this year!

Hall of Champions
2023 – Tossin’ Bags at Bosco’s Social Club
2024 – Chillin’ with Gelato at Divino Gelato Cafe
2025 – Glowin’ Up at Mia Mya’s

2025 Bracket

A few upcoming events...

Outskirts Theatre Co’s Stayin’ Alive: A Night of Disco- Waukesha Civic Theatre

  • 264 W Main Street
  • Adult — $21
    Senior (60+) & Military
    & Subscriber & Group (10+) — $18
    Under 18 — $15
    Educational Group (10+) — $12

Outskirts Theatre Co.’s Stayin’ Alive: A Night of Disco – Waukesha Civic Theatre Get ready to groove with...

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Xeno and Joe- Nice Ash Cigar Bar

  • 323 W Main Street

Calendar – Nice Ash Cigar Bar Expect great music when you hear long time BAD BOY vocalist and...

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Road X, Live Music- Maddy’s Bar & Music Lounge

  • 200 Madison Street

Weekend Music Lineup | Maddy’s

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