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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...

Genealogy 101- Waukesha Public Library

  • 321 Wisconsin Avenue

Month Calendar | Waukesha Public Library Learn how to get started on your genealogical research journey with the...

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Waukesha Wine & Cheese Fest

  • 314 W Main Street
  • $75 for VIP
    $55 per person

Waukesha Wine & Cheese Fest | Facebook Waukesha Wine & Cheese Fest! Saturday, April 5Location: Travieso Restaurant at...

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Guess How Much I Love You- Adventure Walk

  • Frame Park- 1150 Baxter Street
  • Family Registration (max 5): $40/Individual Registration $20

Join us for a 1-mile adventure walk with fun activity stations just in time for the spring season!...

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