Trips & Adventurous Activities in Kissimmee

Check out happening trips & adventurous activities events all around Kissimmee, FL

Silver Spurs Rodeo at Silver Spurs Arena at Osceola Heritage Park

 Fri, 05 Jun at 07:30 pm Silver Spurs Arena at Osceola Heritage Park

iRISE EXPO 2026

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

157th Silver Spurs Rodeo

 Fri, 05 Jun at 07:30 pm 1875 Silver Spur Ln, Kissimmee, FL, United States, Florida 34744

Alex Campos

 Sat, 30 May at 11:00 pm Silver Spurs Arena at Osceola Heritage Park

The Magik and Mythk Festival indoor medieval fair!

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

Spartan Combat Nationals / FAWA State Championships - Both Days

 Sat, 30 May at 07:30 am Events Center at Osceola Heritage Park

Columbus Crew 2 at Orlando City B at Osceola County Stadium at Osceola Heritage Park

 Sun, 28 Jun at 07:00 pm Osceola County Stadium at Osceola Heritage Park

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

 Sat, 03 Oct at 07:30 pm Silver Spurs Arena at Osceola Heritage Park

Spartan Combat Nationals / FAWA State Championships - Saturday

 Sat, 30 May Events Center at Osceola Heritage Park

Unidos en Alabanza

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

Atlanta United 2 at Orlando City B

 Sun, 20 Sep at 06:00 pm Osceola County Stadium

Philadelphia Union II at Orlando City B

 Sun, 21 Jun at 11:00 pm Osceola County Stadium

Medieval Times: Educational Field Trip & Unit Study

Fri, 06 Nov at 10:30 am Medieval Times Dinner & Tournament - Orlando

Orlando City B vs. Carolina Core FC

 Sat, 06 Jun at 07:00 pm Osceola County Stadium At Osceola Heritage Park

Squeeze the Day - Paint and Sip in Orlando | Classpop!™

 Sat, 30 May at 02:00 pm Falcon’s Fire Golf Club USD 39

Carolina Core FC at Orlando City B

 Sun, 07 Jun at 11:00 pm Osceola County Stadium

Chattanooga FC at Orlando City B

 Wed, 19 Aug at 11:00 pm Osceola County Stadium

Philadelphia Union II at Orlando City B at Osceola County Stadium at Osceola Heritage Park

 Sun, 21 Jun at 07:00 pm Osceola County Stadium at Osceola Heritage Park

Singles WEEKEND FISHING KICKBACK

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

MISS MUNDO LATINA LITTLE USA 2026

 Fri, 12 Jun at 05:00 pm Holiday Inn Resort Kissimmee by the Parks by IHG USD 23 to 77

CCW Ultimate Wrestling at Sun on the Beach

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

Pirate and Mermaid Festival

 Sat, 18 Jul at 01:00 pm Violet's Venom Brewery Free

Toronto FC II at Orlando City B

 Sun, 13 Sep at 11:00 pm Osceola County Stadium

Carolina Core FC at Orlando City B at Osceola County Stadium at Osceola Heritage Park

 Sun, 19 Apr at 07:00 pm Osceola County Stadium at Osceola Heritage Park

Coastal Championship Wrestling at Sun on the Beach

 Fri, 12 Jun at 08:00 pm Sun on the Beach

CHAMBERS ARTS

 Thu, 07 May at 05:00 pm Kissimmee City Chambers Park Community Center Free

Crown Legacy FC at Orlando City B at Osceola County Stadium at Osceola Heritage Park

 Sun, 30 Aug at 07:00 pm Osceola County Stadium at Osceola Heritage Park

KLT Travel Magical Meet Ups

 Mon, 15 Jun at 11:00 am Hollywood Studios Entrance Free

Talk Like a Pirate Day ! Let's Celebrate

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

OAK STREET QUILTERS

 Thu, 23 Apr at 09:00 am Oak Street Park Community Center, North Palm Avenue, Kissimmee, FL, USA Free

Crown Legacy FC at Orlando City B

 Sun, 03 May at 11:00 pm Osceola County Stadium

Kooky Kissimmee Scavenger Hunt

 Sun, 30 Jul at 11:00 am Sweety Cafe USD 27

Wspsc

 Sun, 31 May at 03:00 am 5691 Sycamore Canyon Dr, Kissimmee, FL