Winona Business Cup 2026

Three Events. One Cup. Who Will Take Home the Championship?

Get ready for some friendly competition, plenty of laughs, and serious bragging rights! The Winona Business Cup brings area businesses together for three fun-filled events designed to test your knowledge, creativity, communication, and teamwork. Gather your coworkers, create a team name, and get ready to compete for the title of 2026 Winona Business Cup Champion!

Event 1: Business Trivia

Monday, November 9 | 4:00–5:30 PM

How well do YOU know the businesses in our area?

Put your local business knowledge to the test! From familiar favorites to fun facts and surprising history, this trivia competition is all about the businesses that make the Winona area such a great place to live, work, and do business. Think you know Winona? Let's find out!

Event 2: Business Olympics

Tuesday, November 17 | 4-5:30PM

It's time to put your team's communication, creativity, and collaboration skills to the test with three entertaining challenges!

• Communication Breakdown: Can you get your message across? One teammate describes a mystery picture while another attempts to draw it without seeing the original.

• Business Flight Plan: Design, fold, and fly your team's paper airplane toward victory in a target-landing competition.

• Teamwork Takeover: Work together using strings and a rubber band to stack cups without touching them. Communication is everything!

Event 3: Holiday Challenge

Wednesday, November 18 | 4:00–5:30 PM

We're wrapping up the competition with three festive challenges full of holiday cheer!

• Wrap Battle: Two teammates, two hands, one gift! Work together to wrap the perfect present.

• The Frosting Face-Off: Show off your creativity by decorating holiday cookies inspired by your business, the Winona area, and the holiday season.

• Candy Cane Chaos: Hook, move, and race against the clock to transfer as many candy canes as possible!

The Championship Reveal!

Thursday, November 19 | 5:30 PM
Light Up Downtown

The competition is over, the points are tallied, and it's time for the big reveal! Join us at Light Up Downtown as we announce and celebrate the 2026 Winona Business Cup Champion!

Registration & Details

$350 per team | NO LIMIT on team members! Different members can do each event!

Your registration includes:

• Participation in all three Business Cup events

• A beverage and snack at each event

• A $50 donation to local charities

• A chance to win the championship and ultimate bragging rights!

BONUS POINTS! Bring non-perishable food items to each competition to earn extra points while supporting our community.

Whether you're playing to win or simply looking for a fun team-building experience, the Winona Business Cup is a great way to connect with coworkers, celebrate our business community, and give back!

Three Events. One Cup. Let the games begin!