Events & Programs

Art on the Square

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Saturday, June 14 | 9AM - 3PM

Downtown Oskaloosa City Square Park

2025 Event Map Coming Soon!

Live Entertainment

In 2024, Oskaloosa Main Street in welcomed Musical Stringman, Paul Imholte as he performed walking music in the downtown city square. Check back soon for 2025!

2025 Activities in the Main Street District

Window Art Walk around downtown Main Street District Murals
Creative Stations hosted by Main Street District Businesses.

Annual Awards

2024 Art on the Square Award Results

    Best of Show - First Place - Two-Dimensional
Bob King
    Best of Show - First Place - Three-Dimensional
Greg Harris
    Best of Show - Second Place - Two-Dimensional
Laura Larabee
    Best of Show - Second Place - Three-Dimensional
Allison Vial
    Best of Show - Emerging Artist
Osmar Castro
    Best of Show - Honorable Mention
Mike Mittermeier, Lauren Terrell, Sue Burnham, Tarun Dhall

2024 Window Art Walk
1st Place, Most Voted for by the public: Tropical Rayz Salon

Artists: Brooklynn, Maddison, and Kaitlyn

Thank You to Our 2025 Art on the Square Sponsors!