Events & Festivals

Flagship Events in Osceola

1. Osceola Heritage Music Festival

• A beloved annual community event held the third weekend of May, this multi-day festival showcases a mix of classic rock, blues, country, and ’80s music, plus family-friendly activities and great food. It’s a homecoming for many locals. Osceola Heritage MusicfestArkansas+1
• In 2025, it marks its 25th anniversary, set for May 16–17 in downtown Osceola. Osceola Heritage Musicfest

2. Osceola Main Street Farmers’ Market

• Opens in April, with weekly markets every Thursday until late October, hosted on the Courthouse Square. Osceola Main Street

3. 11th Annual Osceola Car Show

• Scheduled for October 18, 2025, this family-friendly display of vehicles takes place in downtown Osceola. Osceola Main Street

4. Trick or Treat on the Town Square

• A fun-filled evening for families and trick-or-treaters on October 28, 2025, complete with a costume contest in Courthouse Square. Osceola Main Street

5. Osceola Christmas Parade & Christmas in the Square

• Celebrates the holidays on December 1, 2025, with festive activities and the classic parade downtown. Osceola Main Street