Around Town · Updated Weekly
Events inKissimmee & St. Cloud
7 Waves Real Estate keeps a weekly guide to what's happening in Kissimmee & St. Cloud, Osceola County — farmers markets, festivals, concerts and live music, arts & entertainment, food-truck nights, nightlife, family fun, and holiday events, including hometown signatures like Osceola County Fair, Now Snowing — Celebration. Add anything to your calendar and get directions in a tap, or browse the interactive calendar a full year ahead.
Curated from Kissimmee's long-running traditions and official calendars. Recurring schedules are the events' usual patterns — confirm with the organizer before you go.
Where
From
What's on
This week7
- SatSep 5
Cirque du Soleil: Drawn to Life
TicketedKissimmee · Walt Disney World, Orlando · 5:30 PM
Ticketed event at Walt Disney World — details and tickets on Ticketmaster.
- SatSep 5
Jack Harlow - Monica Tour
TicketedKissimmee · House of Blues Orlando, Orlando · 6:30 PM
Ticketed event at House of Blues Orlando — details and tickets on Ticketmaster.
- SatSep 5
Cirque du Soleil: Drawn to Life
TicketedKissimmee · Walt Disney World, Orlando · 8:00 PM
Ticketed event at Walt Disney World — details and tickets on Ticketmaster.
- SunSep 6
Cirque du Soleil: Drawn to Life
TicketedKissimmee · Walt Disney World, Orlando · 1:30 PM
Ticketed event at Walt Disney World — details and tickets on Ticketmaster.
- SunSep 6
Cirque du Soleil: Drawn to Life
TicketedKissimmee · Walt Disney World, Orlando · 4:00 PM
Ticketed event at Walt Disney World — details and tickets on Ticketmaster.
- SunSep 6
Labor Day Bash Ft. DJ Icey, DJ Magic Mike, DJ Craze, Baby Anne
TicketedKissimmee · House of Blues Orlando, Orlando · 7:00 PM
Ticketed event at House of Blues Orlando — details and tickets on Ticketmaster.
- WedSep 9
Shriners Children's Showdown at the Net
TicketedKissimmee · ESPN Wide World of Sports State Farm Field House, Kissimmee · 6:30 PM
Ticketed event at ESPN Wide World of Sports State Farm Field House — details and tickets on Ticketmaster.
Save the date — annual signatures
The events each town is famous for, ordered by what's next on the calendar.
Late November–December · Kissimmee
Now Snowing — Celebration
Nightly "snowfall" on Market Street, ice skating, and carolers in Celebration's picture-book town center — a beloved Osceola holiday ritual.
February · Kissimmee
Osceola County Fair
The classic county fair: midway rides, livestock shows, fair food, and rodeo roots that run deep in Osceola's cattle-country history.
Thinking about living in Kissimmee?
Osceola County — Disney's doorstep, Lake Toho bass water, and Florida's vacation-home capital. Explore the full living guide — market snapshot, attractions, flood and insurance reality, schools, and what we tell our buyers.