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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

2024 Bracket

Click the above image to view a larger version

A few upcoming events...

Cordes De Lion, Live Music- Nice Ash Cigar Bar

  • 323 W Main Street

Calendar – Nice Ash Cigar Bar (theniceash.com) A high-class, fun guitar/cello duo for any occasion: weddings, private parties,...

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Professor Pinkerton and the Irrelevant Orchestra- Waukesha Civic Theatre

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

    No Refunds.

Professor Pinkerton and the Irrelevant Orchestra – Waukesha Civic Theatre Professor Pinkerton’s Irrelevant Orchestra maintains an impressive balancing...

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Boeing, Boeing- Waukesha Civic Theatre

  • 264 W Main Street
  • Adult: $30
    Senior (60+) / Military: $27
    Subscriber / Group (10+): $24
    Under 18: $21
    Educational Group (10+): $15

Boeing, Boeing – Waukesha Civic Theatre This 1960’s French farce adapted for the English-speaking stage features self-styled Parisian...

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