- Kissimmee Sunshine Regional Chili Cook-Off
January - International Chili Society sanctioned chili cook-off.
- Kissimmee Festival of Rhythm & Blues
February - One of the largest Black History celebration events in Central Florida.
- Caribbean Fusion
March - Representing a cultural mix of Caribbean and Latino music and dance.
April - Sponsored by Kissimmee West Rotary Club, featuring local high school performers as well as regional acts.
- Symphony in the Park
May - The Concert Series finale, a performance by the Orlando Philharmonic.