Kissimmee Halloween: Boo! on Broadway 5:30-9:30 p.m. Friday, the city's free Trunk or Treat 7-9 p.m. Saturday, Oct. 31, and Sunset Walk's costume contest.

Last checked Oct. 29, 2026. This page is updated each year at the same address. Sources: Kissimmee Main Street’s Boo! on Broadway listing, the City of Kissimmee’s Trunk or Treat page and events calendar, the Osceola Library System’s event calendar, Old Town, the Promenade at Sunset Walk and Gatorland.

Halloween 2026 falls on Saturday, Oct. 31. Kissimmee’s two biggest free nights are back to back: Boo! on Broadway downtown on Friday, Oct. 30, and the city’s Trunk or Treat at Chambers Park on Halloween itself. Old Town on U.S. 192 has its own Halloween night and a haunted attraction, and Sunset Walk has a corn maze through Oct. 30 and an adult costume contest on Halloween night.

Updated Nov. 5: Halloween 2026 has passed. The events below ran Oct. 30 and 31, 2026. This page will be updated for Halloween 2027 at the same address once the city and organizers post their dates, usually in late September.

Updated Oct. 29: Gatorland’s Halloween event has ended, and Friday, Oct. 30, is the last day of The Patch at Sunset Walk. The city’s Trunk or Treat, the costume contest and the library programs were re-checked with the organizers. Daylight saving time ends at 2 a.m. Sunday, Nov. 1.

Trick-or-treat times and candy safety are on a separate page: trick-or-treat hours in Kissimmee.

At a glance

  • Boo! on Broadway: 5:30 to 9:30 p.m. Friday, Oct. 30, Broadway downtown. Free.
  • Trunk or Treat: 7 to 9 p.m. Saturday, Oct. 31, Chambers Park Community Center, 2380 N. Smith St. Free.
  • Sunset Walk Halloween Costume Contest: 6 to 10 p.m. Saturday, Oct. 31, 3251 Margaritaville Blvd. Free to watch.
  • Halloween at Old Town: Saturday, Oct. 31, 5770 W. Irlo Bronson Memorial Highway, 407-396-4888
  • City Parks and Recreation: 407-518-2599
  • Emergency: 911. Police non-emergency: 407-846-3333

Boo! on Broadway, Friday, Oct. 30

Kissimmee Main Street’s Boo! on Broadway is 5:30 to 9:30 p.m. Friday, Oct. 30, on Broadway from Neptune Road to Stewart Avenue: a free, family-friendly night of trick-or-treating at downtown businesses, with costumes, artists and performers along Broadway and the side streets. The Osceola Library System is bringing its OLLie mobile library. The city lists Boo! on Broadway among its community partner events. Kissimmee Main Street: 407-846-4643.

Trunk or Treat at Chambers Park, Saturday, Oct. 31

The City of Kissimmee’s Trunk or Treat is 7 to 9 p.m. Saturday, Oct. 31, at Chambers Park Community Center, 2380 N. Smith St. Kids trick-or-treat from decorated car trunks, with free candy at every trunk, music and Halloween activities. The city says to come in costume and bring a bucket or bag. It is free, open to all ages and needs no sign-up.

Old Town: Halloween night and Mortem Manor

Old Town, the entertainment district at 5770 W. Irlo Bronson Memorial Highway, lists Halloween at Old Town on Oct. 31 among its signature events, alongside its regular Saturday Night Classic Car Show and Cruise, which kicks off at 8:30 p.m. Old Town’s FAQ page says its Mortem Manor haunted attraction is open Wednesday through Sunday from 6 p.m. Old Town is open 11 a.m. to 11 p.m. on Fridays and Saturdays.

Sunset Walk: corn maze, car show and costume contest

The Patch at the Promenade at Sunset Walk ends Friday, Oct. 30, its last day, with pumpkins to pick and paint, a fall photo spot with a tractor and scarecrow, and a corn maze for kids, 3 to 7 p.m. Admission and parking are free and pets are welcome; pumpkins are extra.

  • Trunk or Treat Car and Truck Show (past): this ran 2:30 to 8 p.m. Saturday, Oct. 24, according to the Sunset Walk listing.
  • Halloween Costume Contest: 6 to 10 p.m. Saturday, Oct. 31, on Promenade Plaza. Contestants must be 18 or older and register free through the event page. The top 25 costumes are picked from 8 to 9 p.m. and finalists by audience applause from 9:30 p.m. Sunset Walk lists more than $1,000 in prizes: $600 for first, $400 for second and $200 for third. Spectators get in and park free.

Gatorland’s Halloween weekends (past)

Gatorland’s Gators, Ghosts and Goblins ended Sunday, Oct. 25. It ran on October weekends, 10 a.m. to 5 p.m., included with park admission, with a kids’ costume parade and treat bags.

Library story times and crafts

The Osceola Library System has free Halloween programs at Hart Memorial Central Library, 211 E. Dakin Ave., downtown:

  • Let’s Explore: Cryptids, 5 to 6:30 p.m. Thursday, Oct. 29.
  • Spooky Season Photoshoot, 1 to 4 p.m. Saturday, Oct. 31, Halloween-themed portraits with props and backdrops in the library’s TechCentral studio. Registration required.

At West Osceola Library, 305 Campus St., in Celebration, about eight miles west, Spooky Spectacular: Witches Coven is 6:30 to 8 p.m. Friday, Oct. 30, with crafts and candy after hours (library listing).

On Halloween evening, OLLie is at the City of St. Cloud’s Trunk or Treat from 5 p.m. St. Cloud is about nine miles east.

What this means for you

  • For little kids: the Sunset Walk corn maze on its last day, Friday, and the city’s Trunk or Treat Saturday evening.
  • Downtown on Oct. 30: park once and walk; see our getting around Kissimmee guide.
  • Halloween is a Saturday, so expect busy neighborhood streets from late afternoon.

Related: trick-or-treat hours, things to do in Kissimmee this month and farmers markets.

Frequently asked questions

When is Boo! on Broadway 2026 in Kissimmee?

Friday, Oct. 30, 2026, from 5:30 to 9:30 p.m. on Broadway in downtown Kissimmee, from Neptune Road to Stewart Avenue, according to organizer Kissimmee Main Street. It is a free, family-friendly night of trick-or-treating.

Is there a trunk or treat in Kissimmee on Halloween?

Yes. The City of Kissimmee’s free Trunk or Treat is 7 to 9 p.m. Saturday, Oct. 31, at Chambers Park Community Center, 2380 N. Smith St. It is open to all ages and needs no sign-up.

What is happening at Old Town on Halloween?

Old Town lists Halloween at Old Town on Oct. 31 as one of its signature events. Its Mortem Manor haunted attraction is open Wednesday through Sunday from 6 p.m.

What day is Halloween 2026?

Saturday, Oct. 31. The City of Kissimmee does not set official trick-or-treat hours; our trick-or-treat hours page has the details.