Kissimmee Sign

Kissimmee Main Street

Historic Downtown Kissimmee offers a captivating mix of family-owned businesses, shops, restaurants and special events that cater to a variety of tastes. Historic Downtown Kissimmee EVENTS: April 26: Kowboy Crawl 6pm -9pm 421 Broadway (21 and over only) April 28: Caribbean Fusion Kissimmee Lakefront Park May 4: Cuban Sandwich Festival Kissimmee Lakefront Park May 3: Kissimmee Valley Farmers Market 92 Pleasant Drive May 18: Kissimmee Flea Market 92 Pleasant Drive June 1: PrideFest Kissimmee Kissimmee Civic Center June 15: Juneteenth Festival Kissimmee Civic Center July 4: Monumental Fourth of July Kissimmee Lakefront Park September 7: Fandom Kissimmee Kissimmee Civic Center October 5; Viva Osceola Kissimmee Lakefront Park October 25: 6pm to 9pm BOO ON BROADWAY- Trick or treating event! 205 E. Dakin OR 92 Pleasant Drive


  • EV Charging: No
  • Guided Tours: No Tour Offered
  • Pet Friendly

things to do

  • Duration: Partial Day