Entertainment events in Kissimmee

Check out happening entertainment events all around Kissimmee, FL

Hot Wheels Monster Trucks Live Glow-N-Fire

 Sun, 03 May at 02:30 pm Osceola Heritage Park

Sunset Walk - Orlando July 4th "America 250" Celebration Starring DFALC

 Sat, 04 Jul at 04:00 pm Promenade at Sunset Walk Free

Hot Wheels Monster Trucks Live Glow-N-Fire

 Sat, 02 May at 04:30 pm Silver Spurs Arena at Osceola Heritage Park

Osceola Pride

 Sun, 28 Jun at 12:00 pm 1875 Silver Spur Ln, Kissimmee, FL 34744-6105, United States

Taste of Kissimmee

Fri, 08 May at 05:00 pm Kissimmee Lakefront Park

iRISE EXPO 2026

 Sat, 18 Jul at 12:00 pm 1901 Chief Osceola Trail Free

The Magik and Mythk Festival indoor medieval fair!

 Sat, 22 Aug at 11:00 am Osceola Heritage Park

Promenade at Sunset Walk "Memorial 4 Day Weekend" May 22nd - May 25th

 Fri, 22 May at 05:00 pm Promenade at Sunset Walk Free

Alex Campos

 Sat, 30 May Silver Spurs Arena at Osceola Heritage Park

Sunset Walk Orlando - Kids' 4th of July Family Celebration

 Sat, 04 Jul at 11:00 am Promenade at Sunset Walk Free

"Bon Jovi" Tribute "Slippery When Wet" Live at The Wharf May 24th

 Sun, 24 May at 05:00 pm 3274 Margaritaville Blvd USD 32 to 55

Unidos en Alabanza

 Fri, 29 May at 07:00 pm Silver Spurs Arena

Krush Brau Park Mother’s Day Brunch & Moms Market

 Sun, 10 May at 10:00 am 2198 4 Winds Blvd USD 25 to 67

Spring Soiree

Sat, 09 May at 10:00 am Pioneer Village At Shingle Creek

Party Animals at Loco Beach Coconuts at Champion Stadium at ESPN Wide World of Sports Complex

 Fri, 29 May at 11:59 pm Champion Stadium at ESPN Wide World of Sports Complex

Oddities and Curiosities Expo at Events Center at Osceola Heritage Park

 Sat, 27 Jun at 11:00 am Events Center at Osceola Heritage Park

UNO Kissimmee Mom and Me Deep Dish Pizza Cooking Class

 Sat, 09 May at 12:00 pm UNO Pizzeria & Grill USD 13 to 48

"Thrive & Vibe" Fitness Flight & Wellness Fest Saturday, May 16th 9am - 3pm

 Sat, 16 May at 09:00 am Promenade at Sunset Walk Free

Dive-In Movie!

 Sat, 06 Jun at 07:00 pm 2204 Denn John Ln Free

"Nightrain" The Tribute to "Guns N Roses" Live at The Wharf - June 28th

 Sun, 28 Jun at 05:00 pm 3274 Margaritaville Blvd USD 32 to 55

The "Rod Stewart" Tribute Live at The Wharf - July 12th - On Sale Now

 Sun, 12 Jul at 05:00 pm 3274 Margaritaville Blvd USD 32 to 55

💖🍷 Mom’s Night Out – Mother’s Day Edition! 🍷💖

 Sun, 10 May at 06:00 pm 3038 Dyer Boulevard, Kissimmee, FL 34741

Orlando City B vs. Inter Miami II

 Sat, 23 May at 07:00 pm Osceola County Stadium At Osceola Heritage Park

he Bridgerton Roller Skate Soirée: The Diamond Event of the Season, hosted by Skate Reflections

Sun, 14 Jun at 06:00 pm 1111 Dyer Blvd, Kissimmee, FL 34741-3807, United States, Kissimmee, FL, United States, Florida 34741

2026 Florida Cinderella State Finals

 Fri, 12 Jun at 05:00 am Embassy Suites by Hilton Orlando Lake Buena Vista South

Black Excellence Experience Gala and Fashion Show

 Fri, 24 Jul at 06:00 pm Kissimmee Bay Country Club

New Outlook Events Sunset & Sips: Memorial Weekend Brunch & Day Party

 Sun, 24 May at 12:00 pm FAMA RESTAURANT AND LOUNGE USD 13 to 920

Bloom & Glow Skincare Event

 Mon, 04 May at 05:00 pm Hand & Stone Massage and Facial Spa USD 50

Comedy on Broadway

 Fri, 15 May at 08:00 pm Violet's Venom Brewery Free

Coastal Championship Wrestling at Sun on the Beach

 Fri, 10 Apr at 08:00 pm Sun on the Beach

Singles WEEKEND FISHING KICKBACK

 Fri, 12 Jun at 09:00 am Kissimmee Lakefront Park USD 226 to 376

Applause Talent and Dance Competition

 Fri, 01 May at 02:00 pm 1901 Chief Osceola Trl, Kissimmee, FL 34744-6112, United States

Momentum: A Women’s Leadership Accelerator 2026

 Wed, 23 Sep at 05:30 pm The Inn at Celebration, Autograph Collection USD 425 to 525

THE SOUND OF REVIVAL | WORSHIP CONFERENCE

 Thu, 03 Sep at 07:30 pm Revival Place USD 98 to 162

CCW Ultimate Wrestling at Sun on the Beach

 Fri, 10 Jul Sun on the Beach

LABRFF Orlando 2026 (Brazilian films )

 Thu, 07 May at 07:00 pm Studio Movie Grill (Sunset Walk)

MORNING COFFEE MEET

 Thu, 05 Feb at 10:00 am Kissimmee City Chambers Park Community Center Free

Parking The Party Animals at Loco Beach Coconuts

 Fri, 29 May at 07:30 am The Stadium at the ESPN Wide World of Sports at Disney

Talk Like a Pirate Day ! Let's Celebrate

 Sat, 19 Sep at 12:00 pm Violet's Venom Brewery Free

A Dreamers & Creators Original Market

 Sun, 24 May at 12:00 pm 1901 Chief Osceola Trl, Kissimmee, FL 34744-6112, United States

Kissimmee Scavenger Hunt For Couples - SHOW LOVE (Date Night!!)

 Sun, 03 May Recommended scavenger starting point or other city spot of your choice! (YOU MUST USE PDF TICKETS EMAILED FOR EVENT- NO MOBILE APP OR QR CODES ACCEPTED) USD 10

"Sunset Craft, Food & Drink Market" Every Thursday Evening at 6pm

 Thu, 03 Jun at 05:00 pm Promenade at Sunset Walk Free

Retirement Party for Ms. Gerry Miles

 Wed, 27 May at 10:00 am 1700 Mill Slough Road, Kissimmee, FL, United States, Florida 34744