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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
2026 – Dinner Datin’ at Tofte’s Table

A graphic titled “Main Street Madness Tournament Bracket” shows a multi‑round bracket with activities competing through four stages: Round 1, Round 2, Round 3, and Finals. Each matchup is listed in rectangular boxes connected by lines indicating progression. The Round 1 entries include activities such as “Lookin’ for Local Authors at Martha Merrell’s Books & Toys,” “Watchin’ the Water by the Fox River,” “Dressin’ Like a Diva at Divine Dresses,” “Soothin’ Stresses at Elysian Studio Spa,” “Pumpin’ Up the Pios at Carroll University,” “Dinner Datin’ at Tofte’s Table,” “Pickin’ Pies at Periwinkle Bakery,” “Sourcin’ Sustainability at Plowshare Fair Trade Marketplace,” “Samplin’ Sashimi at Koi Sushi,” “Makin’ Masterpieces at Otto’s Fine Art,” “Easter Eggin’ at the Downtown Bunny Hop,” “Playin’ Poker at Nice Ash Cigar Bar,” “Craftin’ Candles at Waukesha Candle Co.,” “Friday Fish Fryin’ at Matty’s Bar & Grille,” “Traversin’ Trees with Treetop Explorer,” and “Uncoverin’ the Unknown at Waukesha Unlocked.” Winning entries advance through Round 2 and Round 3, where “Dinner Datin’ at Tofte’s Table” and “Soothin’ Stresses at Elysian Studio Spa” appear as the final Round 3 competitors. In the Finals, “Dinner Datin’ at Tofte’s Table” advances. The Champion section at the center of the graphic shows “Dinner Datin’ at Tofte’s Table” as the overall winner. The bottom right corner includes the Downtown Waukesha logo.
Round 1 Matchups

  • Lookin’ for Local Authors at Martha Merrell’s Books & Toys vs Watchin’ the Water by the Fox River **Winner**
  • Dressin’ like a Diva at Divine Dressed vs Soothin’ Stress at Elysian Studio Spa **Winner**
  • Pumpin’ up the Pios at Carroll University vs Dinner Datin’ at Tofte’s Table **Winner**
  • Pickin’ Pies at Periwinkle Bakery **Winner** vs Sourcin’ Sustainibly at Plowshare Fair Trade Marketplace
  • Samplin’ Sashimi at Kumi Sushi **Winner** vs Makin’ Masterpieces at Stroke of Genius
  • Easter Eggin’ at the Bunny Hop vs Playin’ Poker at Nice Ash Cigar Bar **Winner**
  • Craftin’ Candles at Waxed Candle Co. **Winner** vs Friday Fish Fryin’ at Mayor’s Restaurant
  • Traversin’ Trees with Treetop Explorer **Winner** vs Uncoverin’ the Unknown at Waukesha Unlocked

Round 2 Matchups

  • Watchin’ the Water by the Fox River vs Soothin’ Stress at Elysian Studio Spa **Winner**
  • Dinner Datin’ at Tofte’s Table **Winner** vs Pickin’ Pies at Periwinkle Bakery
  • Samplin’ Sashimi at Kumi Sushi vs Playin’ Poker at Nice Ash Cigar Bar
  • Craftin’ Candles at Waxed Candle Co. **Winner** vs Traversin’ Trees with Treetop Explorer

Round 3 Matchups

  • Soothin’ Stress at Elysian Studio Spa vs Dinner Datin’ at Tofte’s Table **Winner**
  • Samplin’ Sashimi at Kumi Sushi vs Craftin’ Candles at Waxed Candle Co. **Winner**

FinalS Matchups

  • Dinner Datin’ at Tofte’s Table **Winner** vs Craftin’ Candles at Waxed Candle Co.

A few upcoming events...

Give Me Moonlight- Waukesha Civic Theatre

  • 264 W Main Street
  • Adult: $22
    Senior (60+) / Military/ Subscriber / Group (10+) / : $19
    Under 18: $16
    Educational Group (10+): $13

Give Me Moonlight – Waukesha Civic Theatre Stuck in the desert of a happily ever after that is...

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The Consequence- Nice Ash Cigar Bar

  • 323 W Main Street

Calendar – Nice Ash Cigar Bar

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Night Fever- Maddy’s Bar & Music Lounge

  • 200 Madison Street
  • $5

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