Events
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Jingle Bar Hop
Kissimmee Main Street 421 Broadway, Kissimmee, FLGrab your crew and jingle all the way through Downtown Kissimmee for our Jingle Bar Hop!Cocktails, mocktails & merry stops at your favorite downtown bars. Early Bird tickets only $25! Festive outfits encouraged — the more sparkle, the better!Let’s turn Broadway into a winter wonderland of cheer. Grab your tickets before they’re gone!
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Christmas Pajama Party
Downtown St. Cloud New York Avenue, St. Cloud, FloridaBreak out your favorite festive pj’s and come for a fun shopping night in Downtown St Cloud! Enjoy a night of festive lights, hot cocoa and holiday shopping. Sip some evening cocktails, grab a bite to eat and don’t skip dessert!
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Greg Warmoth Reindeer Run 5k
SeaWorld Orlando 7007 Sea World Dr., Orlando, FL, United StatesBring the family out for the best Holiday Fun Run in the area. Run or walk the festive 3 mile route through SeaWorld to the sound of holiday bells and finish in a Runner wonderland with holiday treats for all finishers! Dash away to https://www.trackshack.com/event/236 for more information and to register PLEASE NOTE: To participate, […]
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Breakfast with Santa and the Kissimmee Woman’s Club
Kissimmee Woman's Club 1616 W Oak St., Kissimmee, FLThe Kissimmee Woman’s Club invites you to a jolly good time at our Breakfast with Santa at 1616 W Oak Street, Kissimmee, FL 34741! Bring the whole family for a morning full of Christmas cheer. Meet Santa and his elves, enjoy a delicious pancake breakfast, play Candy Bar Bingo, join in story time with children's […]
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2025 Winter Festival – FTC Kissimmee
Florida Technical College 3831 West Vine St., Kissimmee, FLJoin us for Florida Technical College's 2025 Winter Festival, a FREE event that is fun for the whole family. Enjoy holiday cheer, crafts, and a FREE photo with Santa! -Take a picture with Santa-Electronic Device Raffles*-Rumba 100.3 Broadcasting Live on Campus (with giveaways)-Free Kids Haircuts - K through 12**-Free Ice Cream**-Games-Christmas Cookies in the Show […]
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Breakfast with Mrs. Claus
Creative Inspiration Journey School 2030 Old Hickory Tree Rd, St. Cloud, FLJoin us for a festive morning of holiday fun at CIJS — open to the public! Enjoy a delicious pancake breakfast and a lineup of magical activities the whole family will love: Photos with Santa and the GrinchStorytime with Mrs. ClausCookie ContestLife-Size Snow GlobeCrafts and more! Tickets go on sale soon — just $7 per […]
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Association of Poinciana Villages Christmas Parade & Celebration
Villages of Poinciana 625 Country Club Dr., Kissimmee, FLFree event. Parade from Cypress Parkway to the park, followed by a holiday celebration with kids zone, food trucks, live entertainment, vendors & crafters. Great for families — bring chairs/blanket for the parade. Since it’s midday, you may want sunscreen/hats. Check for parking early.
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Christmas Arrives in Narcoossee
Narcoossee School House 5028 Yukon St., St. Cloud, FLJoin us on Saturday, December 13, from 11 a.m. to 2 p.m. for a festive community celebration you won’t want to miss! Photos with Santa (11–2) Write a Letter to Santa Chili Cook-Off & Hot Dogs Local Vendor Market featuring crafts and baked goods
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Christmas Market
Hunter Arms Hotel 1029 New York Avenue, St. Cloud, FLThe Hunter Arms Hotel is excited to bring you our 2nd Pop-Up Market.. with a Christmas twist!!-Last-minute Christmas shopping-Discover unique small businessesFree for all families to come and enjoy!
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Harmony WinterFest Celebration
Harmony Town Square 7254 Five Oaks Dr., St. Cloud, FLJoin us for the WinterFest Celebration on Saturday, December 13 from 5-8pm at Harmony Town Square - a magical evening of community, cheer, and holiday fun! Tree Lighting CeremonyPhotos with SantaGingerbread House ContestTaste of Harmony local eatsLive CarolersToy Drive StationGames, crafts, vendors & more! Gingerbread House Contest Sign-Up: https://forms.office.com/r/EdVeUtaMqZ Cookie Contest Sign-Up:https://forms.office.com/r/3J9cV83CTn(Free to enter – […]
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Soldier City Sundays Weekly Market
Veterans Park 1201 13th Street, St. Cloud, FLJoin us this Sunday from 11 a.m. to 2 p.m. at Veteran’s Park for our weekly community market celebrating St. Cloud’s heritage as the Soldier City.The community is invited to shop from local vendors, enjoy live music, and grab a bite to eat. Veterans can also connect with area veterans organizations all in one place. […]
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Cookies and Cocoa with Santa – Special Sunday Cruise
Old Florida Riverboat Company 1402 Lakeshore Drive, St. Cloud, FLAll aboard for a magical afternoon of holiday fun on the Lillie! Join us for our Cookies & Cocoa with Santa Cruise, the perfect family-friendly Christmas adventure on the water. Guests will enjoy warm cocoa and fresh cookies while playing holiday games, creating festive crafts, listening to story time with Santa, and taking pictures with […]
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Holiday Sensory Night
Lake Eola Park 512 E Washington St, Orlando, United StatesSensory Night is back on Sunday, December 14 from 5:30 pm - 9:30 pm as part of Downtown for the Holidays presented by AdventHealth. Enjoy the magic of the season in a comfortable, low-stimulation environment. We've curated a calm, welcoming holiday experience designed for individuals with sensory sensitivities: No/Low Music: Enjoy the festive atmosphere without […]
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Kissimmee Senior Christmas Brunch
Oak Street Park Community Center 717 N Palm Ave, Kissimmee, FLCelebrate the holidays with friends, family, and neighbors at our free Senior Christmas Brunch! Guests aged 55 and above are invited to enjoy a complimentary holiday meal, music, and festive activities in a warm and welcoming atmosphere. This special holiday event is the perfect way to connect with loved ones, share in the season’s joy, […]
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Kissimmee Senior Christmas Brunch
Oak Street Park Community Center 717 N Palm Ave, Kissimmee, FLCelebrate the holidays with friends, family, and neighbors at our free Senior Christmas Brunch! Guests aged 55 and above are invited to enjoy a complimentary holiday meal, music, and festive activities in a warm and welcoming atmosphere. This special holiday event is the perfect way to connect with loved ones, share in the season’s joy, […]
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Homeschool Winter Party
St. Cloud Civic Center 3001 17th Street,, Saint Cloud, United StatesCelebrate the season with hands-on fun at our Homeschool Winter Party. Students ages 5–14 can enjoy gingerbread decorating, festive activities, and more in a lively winter-themed environment on Wednesday, December 17, from 12 to 2:30 p.m. • $15 per city resident • $20 per non-city resident Register at https://bit.ly/4izRTqO call 407-957-7243 to learn more.
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Wednesday Free Movie Matinee – Featured Film: The Family Man
St Cloud Community Center 3101 17th St, St. Cloud, FLJoin us for a Free Movie Matinee at the Community Center on Wednesday, December 17th, at 12:30 p.m. This month's featured movie: The Family Man This 18+ event is perfect for a mid-week break. Location: Community Center, 3101 17th St. For more info, call 407-957-4243.
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Toddler Holiday Party
St. Cloud Civic Center 3001 17th Street,, Saint Cloud, United StatesCelebrate the season with your little one at our Toddler Holiday Party. Join us for a fun-filled morning designed just for toddlers, featuring festive activities, treats, and holiday cheer in a welcoming environment for families. Event details:- Ages 2–4- $5 resident | $7 non-resident Preregistration is encouraged. Register here:https://webtrac.stcloudfl.gov/webtrac/web/iteminfo.html
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Knockout Christmas Classic
Osceola Heritage ParkKnockout Christmas Classic is the toughest in-season wrestling tournament in the Southeast, bringing in teams from all over the country! Featuring the best high school boys, girls and youth in the country. This year we have added D1. Wrestling fans will not want to miss this event! Children under the age of 6 are free. […]
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Osceola County Sheriff Wrap Attack
Poinciana Lakes Plaza 325 Cypress Parkway, Kissimmee, FLThe Osceola County Sheriff’s Office is excited to host Wrap Attack, a gift-wrapping event by donation in support of Explorer Post 816 and our youth programs. From December 19 through December 22, our Explorers will be on site wrapping your gifts while raising funds that directly support leadership development, mentorship, and positive opportunities for local […]
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Kissimmee Makers Market – Friday Nights
KMS Makers Market 413 Broadway, Kissimmee, FLKissimmee Main Street has invited the Grinch to the Friday night Makers Market the month of December. Join us for games, crafts, vendors, and a weekly “Kids Ugly Sweater” contest.
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Holiday Lights Cruise Featuring the Super Freak Duo
Old Florida Riverboat Company 1402 Lakeshore Drive, St. Cloud, FLHop aboard the beautifully restored “Lillie” for a magical Holiday Lights Tour on the water! Enjoy a festive evening surrounded by sparkling holiday lights, cheerful décor, and the joyful spirit of the season as we cruise into a cozy holiday night. Featuring live music from local favorites Super Freak Duo, this cruise delivers the perfect […]
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Commissioner Brandon Arrington’s Party with Santa
Valencia College Poinciana Campus 3255 Pleasant Hill Road, Kissimmee, FLGet ready for a holiday night your kids will not forget. Join Commissioner Brandon Arrington, Osceola County District 3, for Party With Santa on Friday, December 19, 2025, from 5–7 p.m. at Valencia College – Poinciana Campus, 3255 Pleasant Hill Road, Kissimmee, FL 34746. Photos with Santa (bring your own camera)Face painting, balloon artist and […]
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Knockout Christmas Classic
Osceola Heritage ParkKnockout Christmas Classic is the toughest in-season wrestling tournament in the Southeast, bringing in teams from all over the country! Featuring the best high school boys, girls and youth in the country. This year we have added D1. Wrestling fans will not want to miss this event! Children under the age of 6 are free. […]
