Kissimmee Festivals Events

Festivals Happening Next in Kissimmee, FL

Boots Bulls & Barrels

 Silver Spurs Arena 3 Oct 2025
CONTESTS

Promenade 6th Annual "Trunk or Treat" Trick or Treating & Car Show

 Promenade at Sunset Walk 25 Oct 2025
CAR-SHOWS FREE

Pioneer Day

 2491 Babb Rd, Kissimmee, FL 34746-5803, United States 8 Nov 2025
KIDS

Freestyle 40th Anniversary: George LaMond Trinere Shannon & Corina

 Silver Spurs Arena 10 Oct 2025
TRIPS-ADVENTURES

Spooky Sazón: A Halloween Food Truck Fest

 5403 W Irlo Bronson Memorial Hwy 31 Oct 2025
FOOD-DRINKS FREE

5th Annual Promenade Breast Cancer Awareness Car & Truck Show

 Promenade at Sunset Walk 11 Oct 2025
CAR-SHOWS USD 0 TO 37

Boo On Broadway

 421 Broadway, Kissimmee, FL, United States, Florida 34741 24 Oct 2025
KIDS

Street Art & Eats: A Celebration of Fun & Flavor

 5403 W Irlo Bronson Memorial Hwy 18 Oct 2025
ART FREE

Orlando Japan Festival in Kissimmee 2025

 Kissimmee Lakefront Park 9 Nov 2025
FESTIVALS

[ОРЛАНДО] СУПЕРДИСКОТЕКА 90х и 2000х: ЗОЛОТЫЕ ХИТЫ

 FUMA Lounge 17 Oct 2025

Festival Orgullo Latino: A Celebration of Flavor

 5403 W Irlo Bronson Memorial Hwy 11 Oct 2025
FOOD-DRINKS FREE

MORFFIT VIBES HALLOWEEN EDITION

 Ramada by Wyndham Kissimmee Gateway 25 Oct 2025
HALLOWEEN USD 13 TO 25

Spirit Fest™ Metaphysical & Crystal Expo - Orlando/Osceola

 Osceola Heritage Park 8 Nov 2025
BUSINESS USD 16 TO 23

Boots, Bulls, and Barrels at Silver Spurs Arena at Osceola Heritage Park

 Silver Spurs Arena at Osceola Heritage Park 4 Oct 2025
TRIPS-ADVENTURES

Cider & Showdowns

 Pioneer Village At Shingle Creek 4 Oct 2025
MUSIC

THE BINGO EXPERIENCE: Kissimmee, FL Edition

 Sun On the Beach 18 Oct 2025
CONCERTS USD 36

Osceola Council on Aging 2025 Fall Community Resource Expo

 700 Generation Point, Kissimmee, FL 8 Oct 2025
BUSINESS FREE

Central Florida Veg Fest Silent Auction for the Animals

 Green Acres 25 Oct 2025
FESTIVALS

Krush Brau Dogtoberfest 2026

 Krush Brau Park Portal Immersion Center 14 Mar 2026
MUSIC USD 0 TO 59

Holiday Nights

 210 S Bass Rd, Kissimmee, FL, United States, Florida 34746 21 Dec 2025
KIDS

Hallows Fall Fest 2025

 Krush Brau Park Portal Immersion Center 26 Oct 2025
KIDS USD 0 TO 8

Boots, Bulls, and Barrels

 Silver Spurs Arena at Osceola Heritage Park 4 Oct 2025
TRIPS-ADVENTURES

Silver Spurs Rodeo

 Silver Spurs Arena 18 Feb 2026
RODEO

Parking Noblesville Boom at Osceola Magic

 Silver Spurs Arena at Osceola Heritage Park 5 Feb 2026
CONTESTS

Plant Market Vendor Payments - February 28, 2026 - Plant Market Vendors

 UF/IFAS Extension in Osceola County 28 Feb 2026

ProStreet & Pre-1985 Muscle Car Show

Old Town Kissimmee 1 Nov 2025
MUSIC

Krush Brau Oktoberfest 2025 (Biggest German Beer Garden in the US - 10 AC)

 Krush Brau Park Portal Immersion Center 27 Sep 2025
FESTIVALS USD 0 TO 59

"The Patch" and Pumpkin Painting - Sunset Walk - Open Daily Oct. 17 thru 30

 Promenade at Sunset Walk 17 Oct 2025
MUSIC FREE

Silver Spurs Rodeo at Silver Spurs Arena at Osceola Heritage Park

 Silver Spurs Arena at Osceola Heritage Park 19 Feb 2026
RODEO

Freestyle 40th Anniversary - George Lamond at Silver Spurs Arena at Osceola Heritage Park

 Silver Spurs Arena at Osceola Heritage Park 11 Oct 2025
TRIPS-ADVENTURES