Art Contest

Have an artsy kid?  Enter RAGBRAI's overnight town art contest for the chance to win $350! See below for contest details.

Art Contest Rules

Create an art piece showcasing what RAGBRAI means to you.  One statewide winner from all of the overnight town entries will be chosen and the young artist will win $350. The other entries will be displayed around town to help welcome riders to Winterset on Monday, July 22. To be eligible: 

Contest Rules:

  • Must be a child in grades K-5

  • Winterset’s theme: “Winterset: Where Everyone’s a Winner” should be incorporated into the art

  • Artwork can be no larger than 11” x 14”

  • The artwork can be a drawing, painting or sculpture

  • Child’s name, age, grade, address and phone number must be printed ON THE BACK of the entry

  • The deadline for entries is Saturday, May 18, 2019 by 4 p.m.

  • All entries should be turned in to the Winterset Library, Madison County Chamber of Commerce, Winterset Elementary School office or Winterset Middle School office


Winterset: Where Everyone’s A Winner is all about celebrating the numerous accomplishments and awards this community has received, as well as applauding the riders coming to town for RAGBRAI. Your artwork should incorporate what this looks like to you! To help get you started, think about the following: Do you know someone who is a winner in your mind? What makes the people of RAGBRAI and Winterset special? What traits does a winner have? Use your imagination and have fun! Thank you for helping us decorate the town for RAGBRAI!

If you have any questions, please email us at:

Art Contest Rules Download