Entertainment events in Kissimmee

Check out happening entertainment events all around Kissimmee, FL

Promenade 3rd Annual Halloween Costume Contest $1000's in Cash & Prizes!

 Fri, 31 Oct at 06:00 pm Promenade at Sunset Walk Free

The Wine & Cheese Experience

 Sat, 08 Nov at 07:00 pm Formosa Winery | Island Grove Wine Company USD 23 to 500

Pioneer Day

 Sat, 08 Nov at 10:00 am 2491 Babb Rd, Kissimmee, FL 34746-5803, United States

El George Harris Show Tickets Kissimmee FL Silver Spurs Arena (Orlando area)

 Sun, 09 Nov at 07:00 pm Silver Spurs Arena

Off the Grid Christian Ministries:Fun & Fellowship Community Day

 Sat, 01 Nov at 12:00 pm Kissimmee City Chambers Park Community Center Free

Jeff Dunham

 Fri, 21 Nov at 07:00 pm Silver Spurs Arena

Monster Bulls

 Fri, 13 Feb at 07:00 pm Silver Spurs Arena

Osceola County Pioneer Days

 Sat, 08 Nov at 11:00 am 2491 Babb Rd, Kissimmee, FL 34746-5803, United States

11:11 Sundays - Coffee. Cocktails. Connections.

 Sun, 02 Nov at 11:11 am 2533 Old Vineland Rd suite 2 USD 20

Beyond & Free Spirit Experience

 Wed, 08 Apr at 12:00 am 2145 e irlo Bronson Memorial hwy, Kissimmee, FL, United States, Florida 34744

ORLANDO FASHION KIDS

 Sat, 01 Nov at 06:00 pm 4955 Kyngs Heath Rd USD 29 to 50

Halloween Party

 Fri, 31 Oct at 07:00 pm 205 Lakeview dr, Kissimmee, FL, United States, Florida 34741

Family and Friends

 Sat, 08 Nov at 04:00 pm FUMA Hookah Lounge USD 13 to 269

Holiday Nights

 Sat, 20 Dec at 06:00 pm 210 S Bass Rd, Kissimmee, FL, United States, Florida 34746

12th Annual Fund for Hope Gala Fundraiser

 Sat, 08 Nov at 06:00 pm Kissimmee Civic Centre

Black Cake & Sorrel FL 2025

 Sat, 13 Dec at 07:00 pm MAMMA's Banquets & Events USD 23

Pomp Snow & CIRQUEumstance

 Thu, 13 Nov at 07:00 pm Gaylord Palms Hotel & Convention Center - FL

The Promenade at Sunset Walk Veterans Day Car & Truck Show and Celebration

 Sun, 09 Nov at 11:00 am Promenade at Sunset Walk Free

"Rocking New Year 2026" FREE Concert, Street Party & Fireworks Spectacular!

 Wed, 31 Dec at 07:00 pm Promenade at Sunset Walk USD 0 to 72

Ice Cream for Breakfast with Santa

 Sat, 06 Dec at 09:00 am 210 S Bass Rd, Kissimmee, FL, United States, Florida 34746

Meet the Author: Rebecca Bentley

 Mon, 24 Nov at 06:00 pm 2625 Reading Trail Free

Humanitarian Concert for Myanmar

 Sat, 15 Nov at 06:00 pm Tohopekaliga High School Auditorium USD 109 to 535

Night 1: KC's 80's Kickback

 Fri, 16 Jan at 05:30 pm Hogwarts Inn Free

Halloween Themed End of Month Party

 Wed, 29 Oct at 05:00 pm 850 W. Osceola Pkwy, Kissimmee, FL 34741

George Harris: El Pueblo de Uno

 Sun, 09 Nov at 07:30 pm 1875 Silver Spur Ln, Kissimmee, FL, United States, Florida 34744

Show Car Saturday Nights

 Sat, 07 Nov at 04:00 pm Promenade at Sunset Walk Free

Travursity Travel Showcase, Studio Movie Grill Sunset Walk, Orlando, FL

 Wed, 05 Nov at 05:00 pm Studio Movie Grill - Sunset Walk USD 8

Holiday Nights

 Sun, 21 Dec at 06:00 pm 210 S Bass Rd, Kissimmee, FL, United States, Florida 34746

Kissimmee Movie in the Park (Pending)

 Fri, 05 Dec at 05:00 pm Kissimmee Lakefront Park

Música criolla peruana - comida cacera

 Sun, 26 Oct at 03:00 am Kissimmee Lakefront Park

Jeff Dunham at Silver Spurs Arena at Osceola Heritage Park

 Sat, 22 Nov Silver Spurs Arena at Osceola Heritage Park

ESPN Events Invitational Adventure Bracket - Session 3

 Mon, 24 Nov at 07:00 pm State Farm Field House at ESPN Wide World Of Sports Complex

The Wharf Stage

 Sat, 29 Nov at 06:30 pm The Wharf at Sunset Walk

Poinciana Festival Paint Party!

 Sat, 08 Nov at 10:00 am 3255 Pleasant Hill Rd USD 25

Passport to Presence

 Mon, 27 Oct at 06:30 pm Vintage Vino

Movie in the Park - Lilo & Stitch

 Fri, 07 Nov at 05:30 pm Kissimmee Lakefront Park

Puzzles Entertainment's Halloween Trivia @ Crush Yard Orlando

 Wed, 29 Oct at 07:00 pm Crush Yard Orlando

Ice Cream for Breakfast with Santa

 Sun, 07 Dec at 09:00 am 210 S Bass Rd, Kissimmee, FL, United States, Florida 34746

Osceola County Cinderella Scholarship Pageant

 Sat, 21 Feb at 12:00 pm 1911 Kissimmee Valley Ln, Kissimmee, FL 34744-6107, United States

Osceola Magic - Holiday Party + Replica Jersey Giveaway!

 Tue, 16 Dec at 07:00 pm 1875 Silver Spur Lane, Kissimmee, FL, United States, Florida 34744

Night 3: Terra Nostra

 Sun, 18 Jan at 05:00 pm Hogwarts Inn Free

Krush Brau New Years Eve Party - Free Admission - Reserve Now!

 Wed, 31 Dec at 06:00 pm Krush Brau Park Portal Immersion Center USD 0 to 117

Tribute To Van Halen - Thanksgiving Eve - November 26th! On Sale Now

 Wed, 26 Nov at 05:00 pm 3274 Margaritaville Blvd USD 32 to 55

"Elvis: The Blue Christmas Show" The Tribute to Elvis - December 11th

 Thu, 11 Dec at 05:00 pm 3274 Margaritaville Blvd USD 32 to 55

Memphis Hustle at Osceola Magic at Silver Spurs Arena at Osceola Heritage Park

 Sun, 14 Dec Silver Spurs Arena at Osceola Heritage Park

Parking - George Harris - Comedian

 Mon, 10 Nov at 12:00 am Silver Spurs Arena at Osceola Heritage Park

Venom & Vibes - Standup Comedy

 Fri, 14 Nov at 10:00 am 413 Broadway, Kissimmee, FL, United States, Florida 34741

Krush Brau Dogtoberfest 2026

 Sat, 14 Mar at 12:00 pm Krush Brau Park Portal Immersion Center USD 0 to 59

Kids' Happy Noon Year's Eve Party at Promenade Sunset Walk - Public Welcome

 Wed, 31 Dec at 11:30 am Promenade at Sunset Walk Free

Noblesville Boom at Osceola Magic at Silver Spurs Arena at Osceola Heritage Park

 Wed, 04 Feb Silver Spurs Arena at Osceola Heritage Park

Promenade Racing Car & Truck Show - Friday Nights at 5PM

 Fri, 31 Jan at 05:00 pm Promenade at Sunset Walk Free

Powerful Voices Open Mic Show - Live Music, Comedy, Poetry+ More!

 Thu, 02 Oct at 08:00 pm Kissimmee Free

FNSA Convention 2025

 Wed, 29 Oct at 07:00 am Embassy Suites-Orlando

Jeff Dunham

 Sat, 22 Nov at 10:00 pm Silver Spurs Arena at Osceola Heritage Park

Adventurous Scavenger Hunt - Kissimmee Capers & Curiosities Hunt

 Thu, 14 Nov at 08:00 am 201 Lakeview Dr USD 15

ESPN Events Invitational: Imagination Bracket - Session 1

 Thu, 27 Nov at 10:00 pm ESPN Wide World of Sports - State Farm Field House

Pomp, Snow & CIRQUEumstance at Gaylord Palms Resort and Convention Center

 Fri, 14 Nov at 01:00 pm Gaylord Palms Resort and Convention Center

Parking Noblesville Boom at Osceola Magic

 Thu, 05 Feb at 12:00 am Silver Spurs Arena at Osceola Heritage Park

Parking Cleveland Charge at Osceola Magic

 Thu, 26 Feb at 12:00 am Silver Spurs Arena at Osceola Heritage Park

Parking ESPN Events Invitational: Magic Bracket - Semifinals

 Thu, 27 Nov at 10:00 pm ESPN Wide World of Sports - State Farm Field House

Parking ESPN Events Invitational: Imagination Bracket - Semifinals

 Thu, 27 Nov at 10:00 pm ESPN Wide World of Sports - State Farm Field House

George Harris at Silver Spurs Arena at Osceola Heritage Park

 Sun, 09 Nov at 07:00 pm Silver Spurs Arena at Osceola Heritage Park

ProStreet & Pre-1985 Muscle Car Show

Sat, 01 Nov at 09:00 am Old Town Kissimmee

Barefoot Bay Travelers Club trip to Medieval Times

 Thu, 06 Nov at 03:00 pm Medieval Times Dinner & Tournament - Orlando

Parking ESPN Events Invitational: Adventure Bracket - Session 6

 Wed, 26 Nov at 10:00 pm ESPN Wide World of Sports - State Farm Field House

Family Day with "Mr. Harley" at the Promenade - Sunset Walk Plaza!

 Sat, 21 Sep at 10:00 am Promenade at Sunset Walk Free

George Harris - Comedian

 Mon, 10 Nov at 12:00 am Silver Spurs Arena at Osceola Heritage Park

Pop the Balloon Speed Dating.[Vendors Welcome]

 Wed, 20 Aug at 08:00 pm Kissimmee Free

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

 Fri, 17 Oct at 04:00 pm Promenade at Sunset Walk Free

Promenade Second Sunday Car & Truck Show - FREE Admission & Top 3 Trophies

 Sun, 14 Mar at 11:00 am Promenade at Sunset Walk Free

"Dockside Dueling Pianos" at The Wharf at Sunset Walk EVERY Friday Night

 Sat, 02 Sep at 09:45 pm 3274 Margaritaville Blvd USD 5

"Holinights" Holiday Celebration at Promenade Sunset Walk - Public Welcome

 Thu, 20 Nov at 06:30 pm Promenade at Sunset Walk Free

Sioux Falls Skyforce at Osceola Magic at Silver Spurs Arena at Osceola Heritage Park

 Sun, 01 Mar Silver Spurs Arena at Osceola Heritage Park

On The 7th Day We Brunch ! | Orlando's #1 Brunch Party

 Sun, 13 Nov at 12:00 pm Euphoria Orlando Sushi Lounge Free

ESPN Events Invitational: Magic Bracket - All Sessions

 Thu, 27 Nov at 08:30 am ESPN Wide World of Sports - State Farm Field House

THIS MUST BE THE BRUNCH

 Sun, 04 May at 01:00 pm Euphoria Kissimmee Free

Parking Wisconsin Herd at Osceola Magic

 Wed, 11 Mar at 11:00 pm Silver Spurs Arena at Osceola Heritage Park

The Wonderful Wizard of Oz Experience - Kissimmee

 Mon, 22 Sep at 08:00 am The Wonderful Wizard of Oz Experience - Kissimmee USD 24 to 64

An Action-Packed Scavenger Hunt! - Bay Lake Buccaneer‘s Bonanza

 Wed, 15 Jan at 08:00 am Building 1 USD 15

A Date Night Adventure! - Kissimmee Capers & Curiosities Hunt

 Wed, 04 Jun at 08:00 am 201 Lakeview Dr USD 36

Parking ESPN Events Invitational: Imagination Bracket - All Sessions

 Thu, 27 Nov at 08:30 am ESPN Wide World of Sports - State Farm Field House