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Events & Programs

Art on the Square

Join us for the 55th Annual Art on the Square, one of Iowa's oldest continuing art festivals, on Saturday, June 8 in the downtown city square park.

Art on the Square 2024

Saturday, June 8 | 9AM- 3PM 

Downtown Oskaloosa City Square Park

Artist Application Information

Early Bird Deadline: April 12, 2024

Final Deadline: May 3, 2024

2024 Art Vendor Application Fillable 

2024 Art Vendor Application Print

High School Emerging Application Fillable 

High School Emerging Application Print 

Questions?  Contact Oskaloosa Main Street or call 641-672-2591.

Looking to Volunteer? 2024 Volunteer Sign-Up Coming Soon! 

Sign Up Here!


2024 Food Vendors 
  • Coffee Cruiser - Espresso drinks, smoothies, Italian sodas

  • Eatery Island - Fresh Squeezed lemonade, corn dogs, funnel cakes, hot dogs

  • Grubby's Kettle Korn

  • Mr. Taco - Tacos, Walking Tacos, Drinks, & more

  • My Eatzz - BBQ favorites 

  • Pho T - Vietnamese food truck with Pho soup, egg rolls, and more

  • SnoBiz

  • Tacos Jalisco - Tacos, burritos, totas, quesadillas 

Interested in Being a Food Vendor? 

Food Vendor Inquiry

Live Entertainment 

Join Oskaloosa Main Street in welcoming Musical Stringman, Paul Imholte as he performs walking music in the downtown city square. 

2024 Activities in the Main Street District

  • Window Art Walk around downtown Main Street District Murals will be up from June 8 to June 30. 

  • Creative Stations hosted by Main Street District Businesses. 


2023 Art on the Square Award Results

    Best of Show - First Place - Two-Dimensional
        Laura Larabee 
    Best of Show - First Place - Three-Dimensional
        Dan Kemp
    Best of Show - Second Place - Two-Dimensional
        Chris Abigt
    Best of Show - Second Place - Three-Dimensional
        Michael Tygart
    Best of Show - Emerging Artist
        Ava Westercamp
    Best of Show - Honorable Mention
        Meg Prange
        Megan Hammer
        Joshua Steele
        Doug Adams 

    Window Art Walk
        1st Place, Most Voted: Tropical Rayz - Hailey Curry 






 Art on the Square Map COMING SOON!


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