Halloween Costume Contests in Kissimmee 2026

31Oct

Promenade - Sunset Walk Halloween Costume Contest $1000's in Cash & Prizes!

Promenade at Sunset Walk

31 Oct 2026

FREE

30Oct

BOO! on Broadway

Historic Downtown Kissimmee

30 Oct 2026

31Oct

Biggest Halloween Party in Kissimmee

The Amador Gallery

31 Oct 2026

USD 18

31Oct

Trunk or Treat

Kissimmee City Chambers Park Community Center

31 Oct 2026

FREE

31Oct

The Gallery of Sins: A Halloween Masquerade

The Amador Gallery Event Venue

31 Oct 2026

USD 0 TO 461

31Oct

4th Annual Trunk or Treat by the Kissimmee Woman's Club

1616 W Oak St, Kissimmee, FL 34741-4080, United States

31 Oct 2026

23Oct

Kissimmee Costume Party featuring DJ Phat Tony | Salsa Heat

401 N Main St, Kissimmee, FL 34744-5260, United States

23 Oct 2026

26Oct

Osceola Homeschool Friends & Homeschool Hive’s Annual Halloween Party & Trick or Treat

Kissimmee Lakefront Park

26 Oct 2026

31Oct

Halloween Afters

Kissimmee

31 Oct 2026

5Dec

Wizarding World Luau Dinner Show

4740 W Irlo Bronson Memorial Hwy Kissimmee, FL 34746

5 Dec 2026