Calendar of Events
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Downtown Kissimmee shines bright this holiday season during the Festival of Lights, a free celebration transforming the heart of the city into a glowing holiday destination. Thousands of twinkling white lights stretch across Broadway, side streets, and Kissimmee Lakefront Park, creating a magical atmosphere for families, couples, and visitors to enjoy nightly. Explore downtown shops, […] |
2 events,
Osceola County Commissioner Viviana Janer (District 2) invites you to the official unveiling of OLLie, the Osceola Library System’s newest Mobile Library Unit! Join us as we introduce a new way to bring library services directly to our community. OLLie will offer:• Library cards• Storytimes• Tech tutoring• Holds pickup• On-the-go library programming This mobile library […] |
2 events,
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Be serenaded by the intricate holiday harmonies of the Brass Band of Central Florida, helping us kick off the 2025-2026 Celebration Foundation "World Showcase" Concert Series.
$40
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2 events,
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The Women's Ministry of Kissimmee Christian Church will present the Holiday Gift Market on Thursday, December 4, from 5 to 8 p.m. at Kissimmee Christian Church, 415 N. Main Street, Kissimmee, FL 34744. Join us for an evening of shopping and fun, and get into the holiday spirit! This is the perfect chance to find […] |
5 events,
Downtown St Cloud is full of festivities this holiday season. Shop, dine & enjoy the downtown community this season. We hope this little list of dates helps in the busy season and stay tuned as we continue to post more about specific upcoming events. 
Kissimmee 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. 
Kick off the holiday season with a magical night at Movie in the Park! Join us at Kissimmee Lakefront Park on December 5 for a festive screening of Home Alone 2, featuring family-friendly fun, including free crafts, inflatables, a photo booth with Santa, and holiday-themed crafts.To add to the spirit of giving, bring a canned […]
Free
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Celebrate the season at the Annual Tree Lighting - Winter Wonderland Ceremony on Friday, December 5, from 6 p.m. to 9 p.m. at St. Cloud City Hall, 1300 9th Street. Enjoy an evening filled with musical performances, crafts, letters to the North Pole, visits with Santa, carnival games, snowslide, inflatables, and more festive fun for […] |
9 events,
Get ready to dash through the sunshine for the Oh, What Fun! Run 5k at Lake Nona Town Center on December 6 at 7:30 a.m.! Lace up your running shoes, dress in your best holiday and celebrate the season with a fun-filled run. Whether you're sprinting, jogging, or walking with friends and family, it's a […]
$45
Get ready for a full day of festive fun in the heart of St. Cloud! This year’s Holiday Festival brings together local crafters and artists, live performances, an exciting Kids Zone the whole family will love, fabulous food trucks, and MUCH more. Don’t miss your chance to grab photos with Santa, enjoy delicious festival food, […]
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The Annual Christmas parade, presented by Orlando Health St. Cloud Hospital and the City of Saint Cloud, is brought to you by Experience Kissimmee. This year's theme for the Christmas parade is "The Magic of Christmas." The St. Cloud Christmas parade is a family-friendly event, featuring festivities for all ages. This locally televised event will […]
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Enjoy a self-guided tour through beautifully decorated homes throughout Celebration as you soak in the sights, sounds, and spirit of the season. Your ticket also includes access to the Magical Marketplace - an extravagant array of holiday décor, themed trees, stunning vignettes, and baskets galore, all available for purchase.
$25
Grab your most wonderfully tacky holiday sweater and join us aboard the Lillie for a festive Christmas Carols & Ugly Sweater Cruise! Set sail at 5 p.m. for an evening of merry music, twinkling lights, and plenty of holiday cheer on the water. Sing along to your favorite Christmas carols, show off your ugliest (and […]
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Join us right before our weekly Car Cruise as residents from Sherwood Forest RV Resort present their personal golf carts in all of their Holiday glory! Golf carts will begin arriving at 6:30pm and will parade down Old Town’s MainStreet before our Car Cruise at 8:30pm. 
Poker tournament to raise money for Christmas gifts for families in need this holiday season! Pre-register for an additional $5000 in chips! Pre-registration requires pre-payment! |
5 events,
Get ready for a full day of festive fun in the heart of St. Cloud! This year’s Holiday Festival brings together local crafters and artists, live performances, an exciting Kids Zone the whole family will love, fabulous food trucks, and MUCH more. Don’t miss your chance to grab photos with Santa, enjoy delicious festival food, […]
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Hop aboard the beautifully restored “Lillie” for a serene Sunday morning on the water! Enjoy a delightful selection of fresh muffins, sparkling mimosas, and gentle morning breezes as we cruise in classic Old Florida charm.Only $24.99 per person and $10 for bottomless mimosas.The Lillie is an authentic sternwheeler, lovingly restored and named after the historic […]
$24.99
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Enjoy a self-guided tour through beautifully decorated homes throughout Celebration as you soak in the sights, sounds, and spirit of the season. Your ticket also includes access to the Magical Marketplace - an extravagant array of holiday décor, themed trees, stunning vignettes, and baskets galore, all available for purchase.
$25
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6 events,
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Santa is coming to Pioneer Village! Celebrate the season with us at this festive holiday event featuring: Christmas carolers, local vendors, delicious food, crafts & pioneer games, a chance to deliver letters to Santa …and more! Admission: $5 (Kids 2 & under are free!)
$5
Kissimmee 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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Grab 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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Break 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! |
10 events,
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Bring 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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The 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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Join 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 […]
Free
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Join 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 […]
$7
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Join 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
Free
Free 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.
Free
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The 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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Join 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 – […] |
3 events,
Join 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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All 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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Celebrate 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, […]
Free
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Celebrate 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, […]
Free
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Join 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. |
1 event,
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5 events,
Knockout 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. […]
Kissimmee 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. 
Hop 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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Get 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 […] |
6 events,
Knockout 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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Annual event for kids. Each child gets breakfast, goodie bag, a book and a visit with Santa Claus. Live music by Denny GeeDoor prizes and elves Contact Linda Lokken for tickets407-569-7688
$15
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Join us for our 21st annual Breakfast with Santa! This year, come cozy in your favorite pajamas for a festive and magical morning. Families will enjoy a free breakfast spread, meet Santa, take holiday photos, and celebrate the season together. Don’t miss this heartwarming event that has been creating memories for two decades.
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Grab your friends and your ugliest Christmas sweater for December’s wine walk in the Cloud! Get your tickets on the Eventbrite link below. Returning wine walkers buy your tix on site and bring your reusable plastic glass back with you to save five dollars off! https://www.eventbrite.com/e/wine-walk-in-the-cloud-tickets-1076743742519?aff=erelpanelorg
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Hop 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 — featuring live music by Skart from The Supervillains — as we cruise into a cozy holiday night. The Lillie offers a […] |
2 events,
Join 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. […] 
Join the Old Florida River Boat Company for a unique Holiday Fundraiser Cruise aboard The Lillie!Enjoy a relaxing scenic cruise on the beautiful East Lake Toho while being entertained by a captivating, LIVE radio play! It’s nostalgic fun for a wonderful cause. Departure: 3:00 p.m. sharp!Location: 1402 Lakeshore Blvd, St Cloud, FL 34769 Book your […] |
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Surfing Santas 2025 is on Christmas Eve, 7:30 a.m. Where: End of Minutemen Causeway, in front of Coconuts on the Beach Hundreds of Surfing Santas will hit the waves, and thousands of spectators will fill the beach to celebrate love, joy, and holiday spirit together again. What started as a fun family surf day in […]
Free
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Join us for some coffee and car talk. The term “exotic” is used in marketing by automakers to mean “unusual or expensive,” but we like to think it means “the type of vehicle that dreams are made of.” Take in the sites of these exotic vehicles on display selected Sunday mornings of each month on […]
Join 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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End 2025 with a bang at a New Year's Eve Celebration presented by Old Town and Fun Spot.Bring the family for Live Music & Entertainment featuring the band DRAW 4 and a drone show at midnight.At midnight, watch the night sky illuminate with a fantastic drone show closing out 2025 and ringing in the new […] 
St. Cloud’s biggest New Year’s Eve celebration returns. Rockin’ the Cloud takes place Wednesday, December 31, from 7 p.m. to 1 a.m. in Historic Downtown St. Cloud. We are excited to welcome Less Than Jake as this year’s main stage headliner! Enjoy free general admission or elevate your night with our $75 Cloud VIP experience, […] |
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1 event,
Join 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. […] |
