Expect festive live music, cozy rides on the Pearl Express Train Tour, and magical appearances from Santa, his elves, and toy soldiers. Join the Promenade at Sunset Walk for their annual Holinights Celebration, featuring Santa Claus and his Mischievous Elves, towering toy soldiers, and the nightly lighting of the beautiful 40-foot animated Holinights Christmas tree at 6:30 pm. The Holinights Celebration takes place on select nights from November 20 – December 25, 2025, 6.30 p

Step into a world of wonder this holiday season with POMP, SNOW & CIRQUEumstance, an immersive new show for the entire family. A brand-new cirque spectacle comes to life this holidy season with the debut of POMP, SNOW & CIRQUEumstance at Gaylord Palms Resort in Kissimmee, This immersive, cirque holiday show and experience, created by Broadway director and “Cirque Dreams” founder Neil Goldberg, will be presented inside the Gaylord Palms atrium Nov. 14, 2025-Jan. 4, 2026. The s

Attention parents, guardians, and kids! Join Promenade at Sunset Walk and work together to create safer roads for everyone! Get ready for an exciting day as the Promenade at Sunset Walk and Osceola County Sheriff’s Office present “Touch A Truck & Safety Talks.” See and explore awesome trucks and learn important Safety Tips. Don’t miss out on this unique opportunity to interact with cool vehicles and learn about safety in a fun and engaging way! Explore exciting trucks includi

The annual Pioneer Day celebrates Osceola County’s first residents and the pioneering spirit of the late 19th century, hosted at the Pioneer Village at Shingle Creek in Kissimmee. The annual Pioneer Day celebrates Osceola County’s first residents and the pioneering spirit of the late 19th century. Step back in time at this annual festival hosted at the Pioneer Village at Shingle Creek in Kissimmee. Pioneer Day taking place on Saturday, November 8 from 10 am - 4 pm is a free,

Each year in November, the popular Orlando Japan Festival takes place in Kissimmee, where visitors to the festival can experience authentic Japanese music, dance and other entertainment. Experience the beauty, culture, and tradition of Japan right in Kissimmee, with the annual Orlando Japan Festival returning to Kissimmee's Lakefront Park for a day of performances, food, art, and family-friendly activities. This year’s Orlando Japan Festival takes place this weekend, on Sunda

The City of Kissimmee's popular Movie in the Park returns this weekend with KUA once again presenting the popular community event at Kissimmee Lakefront Park. Kissimmee Utility Authority, in partnership with the City of Kissimmee, will once again host a free Movie in the Park event on Friday, November 7, 2025 , at the Veterans Lawn of Kissimmee Lakefront Park. KUA’s Movie in the Park series is held on the first Friday of every month, October through March. Friday's event wi

Celebrate the spookiest of holidays at Old Town in Kissimmee with a night of good old fashioned family fun. Grab your little ghoul or goblin for a night of frightful fun at Old Town on Friday, October 31, 2025. Celebrate the spookiest of holidays with free Trunk or Treat, thrilling Halloween entertainment, and a fang-tastic Costume Contest. Collect sweet treats at candy stations throughout Old Town during free Trunk or Treat from 5 pm to 7 pm, while supplies last. Show off yo

Wood Fire Rotisserie Turkey makes holiday hosting easy with Heat-and-Serve Meals and Online Gift Card Offer. The busy holiday season is almost here, and Cowboy Chicken , known for its delicious wood fire rotisserie chicken, turns to turkeys for the ultimate menu inspiration. Cowboy Chicken’s holiday meal packages and catering options will turn any gathering into a flavor-packed party. And, for a limited time, the eatery is offering a “Spend $50, Get $10” promotion for e-gift

Bring the whole family for d ecorated cars, costumes, non-stop entertainment, and LOTS of candy for the kids. Embrace the Halloween spirit at the annual Promenade at Sunset Walk Trunk or Treat Car Show, a fun for all the family Trick-or-Treating Event & Car Show this weekend! On Saturday , October 25, drive on over with your spooky squad to the Promenade at Sunset Walk which is located just off the 192 in Kissimmee where you can enjoy dozens of candy locations, plus candy d

T ake SunRail to the Kissimmee Station and walk a few steps right into the fun. Enjoy trick-or-treating, games, live entertainment, and family-friendly Halloween excitement. Regular fares apply. SunRail is providing extra service to the exciting Boo! on Broadway event in Kissimmee on Friday, October 24, 2025, from 6 pm to 9 pm. Participants can enjoy spooky fun, trick-or-treating, live entertainment, food trucks, and family-friendly activities on Kissimmee’s Broadway Street.

BOO! On Broadway features live music, dance performances, DJ, entertainment, candy, photo booths, and surprises. Boo! On Broadway is a much loved community event bringing safe, community trick or treating to downtown Kissimmee’s Broadway, with free fun for all the family to enjoy. Organized by Kissimmee Main Street, this annual family-friendly Halloween celebration is the biggest Halloween event is Osceola County, and attracts thousands of attendees, featuring trick-or-treat

This new service offers quick access to kayaks seven days a week, from sunrise to sunset, allowing you to paddle whenever you want. The City of Kissimmee Parks and Recreation Department has introduced a new outdoor recreation service at Shingle Creek Regional Park: self-service kayak rentals, now available seven days a week from sunrise to sunset. This new amenity is provided in partnership with Whenever Watersports and is designed to make kayaking more accessible and conveni

Enjoy a fall-filled day at Wild Florida this spooky season on Saturday, October 18. Get ready for a gourd-geous day of family fun... Wild Florida is bringing back Pumpkin Fest, a one-of-a-kind fall event that will make you fall in love with the season all over again! Join Wild Florida on October 18, from 10 am to 4 pm, for an unforgettable day celebrating everything autumn alongside some of the world’s coolest animals you can meet at Wild Florida. Get ready for some colorful

The fast-growing cheeseburger slider brand, known for serving fresh, cooked-to-order cheeseburger sliders, seasoned waffle fries, and...

In partnership with Atlas Obscura, the trail showcases Osceola County’s vibrant Hispanic and Latino food culture, from bustling food...