• FREE Family Movie Night

    Studio Movie Grill - Margaritaville 3204 Margaritaville Blvd, Kissimmee, FL

    Commissioner Peggy Choudhry (D2) is hosting a FREE Family Movie Night for Osceola County residents! Come enjoy an evening of family fun with a showing of Zootopia 2 at Studio Movie Grill. Wednesday, November 26, 2025Check-in begins at 6:15 p.m.Movie starts at 7:30 p.m. (Theatre 5) Event Details:• Free for Osceola County residents• 2 free […]

    Free
  • Santa Calling!

    'Tis the season for Santa Calling!  Schedule a special call from Santa or Mrs. Claus and create magical memories for your family this holiday season. The calls will take place on Thursday, December 4, and you must register by November 27 at kissimmee.gov/santacalling.

  • Southeast Region Cheer and Dance Regional Competition

    Osceola Heritage Park

     More than 550 Cheer & Dance teams from Florida and Georgia will compete for the Title of Regional Champion and the opportunity to advance to the Pop Warner National Championships. Advance online sales will end on 11/23/25 at 5:00pm. You can purchase tickets in advance at the host hotel starting 11/27/25, or on-site at the […]

  • Sunset Cruise – Live Music Featuring Mauricio Camacho

    Old Florida Riverboat Company 1402 Lakeshore Drive, St. Cloud, FL

    Hop aboard for an epic adventure on the beautifully restored "Lillie," an authentic sternwheeler named after a historic vessel that operated on the shores of East Lake in the late 1800s.Featuring live music from local artist Mauricio Camacho. The Lillie has a full bar, but don't you worry, plenty of nonalcoholic options on board as […]

  • Kissimmee Festival of Lights

    Downtown Kissimmee +1 more

    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, […]

  • Small Business Saturday

    Downtown St. Cloud New York Avenue, St. Cloud, Florida

    Small Business Saturday is coming up on November 29, 2025!This day is all about showing love to the independent shops, makers, and local favorites that give our community its character. When you shop small, you’re not just buying a product—you’re helping local owners thrive, supporting local jobs, and keeping money circulating right here at home. […]

  • St. Cloud Monthly Market at AMVETS Post 33

    AMVETS Post 33 4310 Deer Run Drive, St. Cloud, FL

    Buy, Sell, Eat, Drink and have fun. Last Saturday of every month. There will crafts, art, yard sales, and farmers market. Food for the family. Bounce house for the kids and beer for the adults. Booths are FREE to AMVET Post 33 members, so sign up today. For booth rentals contact Jim @ 407-729-6787.

    Free
  • Starry Night Christmas Festival

    Sunbridge 6197 Cyrils Drive, St. Cloud, FL

    Holiday Tree Lighting Celebration at Sunbridge!Enjoy a night full of holiday fun: Visits with Mr. & Mrs. Claus: Snap a photo and share your wish listFestive Market: Shop for unique gifts and handcrafted treasures from local artisansMagical Snowfall: Experience a flurry of “snow” right here in Sunbridge Food Trucks: Savor seasonal bites and sweet treats […]

    Free
  • Sunset Cruise With Live Music Featuring Afterglow

    Old Florida Riverboat Company 1402 Lakeshore Drive, St. Cloud, FL

    Hop aboard for an epic adventure on the beautifully restored "Lillie," an authentic sternwheeler named after a historic vessel that operated on the shores of East Lake in the late 1800s. Featuring live music from local artists Afterglow.The Lillie has a full bar, but don't you worry, plenty of nonalcoholic options on board as well. […]

  • Kissimmee Tree Lighting Ceremony

    Kissimmee City Hall 101 Church Street, Kissimmee, FL

    Let’s kick off the holiday season at our annual Tree Lighting Ceremony! Join us for an evening filled with holiday cheer, featuring the official downtown Kissimmee tree lighting, a special visit from Santa Claus, and a festive musical performance to kick off the season. Bring your family and friends! We hope to see you there! […]

  • Soldier City Sundays Weekly Market

    Veterans Park 1201 13th Street, St. Cloud, FL

    Join us Sundays 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.Every Sunday! […]

  • Worship on the Water

    Old Florida Riverboat Company 1402 Lakeshore Drive, St. Cloud, FL

    Join us aboard the Lillie for a peaceful and uplifting Worship on the Water experience — a special afternoon of fellowship, praise, Christian music, prayer, and reflection surrounded by God's beautiful creation. Gang plank opens at 1:30 PM Come rejoice, refresh your spirit, and enjoy the calm waters as we gather in faith and community. […]

    $19.99
  • Mobile Library Unit Unveiling with Commissioner Viviana Janer

    Buenaventura Lakes Library 405 Buenaventura Blvd, Kissimmee, FL

    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 […]

  • Brass Band of Central Florida Holiday Concert

    Community Presbyterian Church in Celebration 511 Celebration Ave, Kissimmee, FL

    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
  • Holiday Gift Market

    Kissimmee Christian Church 415 N Main Street, Kissimmee, FL

    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 […]

  • St. Cloud 2025 Holiday Events

    Downtown St. Cloud New York Avenue, St. Cloud, Florida

    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.

  • KUA Movie in the Park: Home Alone 2

    Kissimmee Lakefront Park

    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
  • Annual Tree Lighting Winter Wonderland Ceremony

    St. Cloud City Hall 1300 9th St, St. Cloud, FL

    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 […]

  • Oh, What Fun! Run 5k

    Lake Nona Town Center 13630 Sachs Avenue, Orlando, FL

    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
  • St. Cloud Holiday Festival

    St. Cloud Holiday Festival

    Downtown St. Cloud New York Avenue, St. Cloud, Florida

    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, […]

  • 2025 St. Cloud Christmas Parade presented by Orlando Health – St. Cloud Hospital

    Downtown St. Cloud New York Avenue, St. Cloud, Florida

    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 […]

  • 2025 Holiday Home Tour & Magical Marketplace

    Celebration Celebration, FL

    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
  • Christmas Carols & Ugly Sweaters – Holiday Lights Cruise

    Old Florida Riverboat Company 1402 Lakeshore Drive, St. Cloud, FL

    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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