ORLANDO — The recent cold spell that sent Orlando’s temperatures into the 30s was an unexpected surprise for November, especially considering that Floridians are used to spending Christmas day in shorts, t-shirt, or even their pool. Still, one fun aspect of the cold spell is that it helps get Orlando residents and visitors alike into the spirit of those nostalgic Christmas’ of hot chocolate, thick hats, and Winter holiday delights.

The City of Orlando is certainly doing its part to get everybody in the holiday spirit, and so are a lot of local attractions, museums, theaters and concert halls in this tourist hotspot. If you’re in Central Florida in November and December and are looking for holiday cheer, boy have you come to the right place!

Working with the City of Orlando, Freeline Media has compiled a comprehensive list of upcoming city-sponsored holiday fun available here, now through the end of the year. Grab your calendars and starting checking off all those must-see Christmas events!

What’s Happening in Orlando Around The Holidays?

Sunny Orlando for holiday fun? Absolutely, the office of Mayor Buddy Dyer is quick to note.

“The most wonderful time of the year is here in Orlando,” notes Andrea Otero, public information officer for the mayor’s office, in a news release inviting the public to celebrate the season in Orlando.

“Throughout November and December, the City of Orlando invites Central Florida residents and guests to celebrate the holidays with family-friendly holiday events and activities for all ages to enjoy, furthering the city’s continued commitment to providing a wide variety of entertainment and festivities for everyone,” she adds.  

With so many tourist-friendly institutions and entertainment venues eager to compete for visitors during the holiday season, this tourism mecca has a long list of holiday fun to offer. So let’s dive in to what the City of Orlando government is offering locals and our many visitors this most joyous season.

Holiday Calendar for Central Florida

• Sunday, Nov. 16 at 3 p.m. – Handel’s Messiah at Dr. Phillips Center for the Performing Arts, 445 S. Magnolia Ave. 
  “For over five decades, the Messiah Choral Society of Central Florida has presented a moving, fully orchestrated performance of Handel’s Messiah completely free to the public. Held each November in the world-class Steinmetz Hall, this beloved concert features professional soloists, a full orchestra and a powerful volunteer choir under the direction of acclaimed conductor Dr. John V. Sinclair.”

• Wednesday, Nov. 19 through Friday, Dec. 12, Districts of Cheer: Orlando Main Streets Holiday Window Decorating Contest 
  “Visit any of the 12 Orlando Main Streets Districts beginning Nov. 29 for a festive display of holiday creativity and spirit. Participating businesses will have their windows and facades decorated for the holiday as part of the larger 12 Districts of Cheer: Orlando Main Streets Holiday Window Decorating Contest, and invite residents and visitors to enjoy these displays of local art as they shop and dine in our districts throughout the holiday season.” 
  
• Thursday, Nov. 20 through Monday, Nov. 24, it’s the Lake Eola Christmas Tree Installation at
  Lake Eola Park, 195 N. Rosalind Ave.  
  “The Lake Eola Christmas tree will be installed at Lake Eola Park’s Washington Plaza over the course of four days. The 64-foot tree will be adorned with close to 2,000 ornaments and 200 pounds of lights, which will musically sync with the lights on the Lake Eola fountain and will provide animation during the shows.”
• Thursday, Nov. 20 at 6 p.m. – City District’s Deck the District, Church Street Plaza, 54 W. Church St.  
  “City District’s signature Deck the District will feature the much-anticipated gingerbread house building contest, Santa Paws to take pictures with you and your pets, a live band, and the lighting of the Christmas tree to cap off the night of fun at 8:30 pm.”    
  
• Saturday, Nov. 22 at 4:30 p.m., it’s Jingle Eve at Ivanhoe Village starting at Gaston Edwards Park, 1236 N. Orange Ave.  
  “Annually organized by the Ivanhoe Village Main Street District, Jingle Eve is a family-friendly holiday celebration featuring a beer garden, wine walk, food trucks, local artists, vendors, a children’s holiday village with arts and crafts and a bubble bus, fireworks, special event promotions by Ivanhoe Village businesses and live musical performances.”  
  
  7 p.m. – Clare and The Chocolate Nutcracker  at Dr. Phillips Center.
• “Clare and the Chocolate Nutcracker is an original adaptation of the classic Nutcracker ballet. The audience will take a magical journey with Clare through her enchanting dream where she travels with the Chocolate Nutcracker and the Sugar Plum Fairy around the world. Purchase tickets at drphillipscenter.org/clare-and-the-chocolate-nutcracker. 
  
• Sunday, Nov. 23 at 8 a.m., it’s the Jack Kazanzas Star Installation in Downtown Orlando.
• “An Orlando holiday tradition, the raising of the Jack Kazanzas Star will be hung 50 feet above downtown Orlando at the intersection of Orange Avenue and Pine Street. The more than 50-year tradition of raising the 600-pound golden star started in the 1950s. Since then, the star has come to symbolize the start of the holiday season in Orlando.”
  
• Friday, Nov. 28 through Sunday, Jan. 4, 2025 from 9 a.m.- 4 p.m., it’s Holidays at Leu Gardens, 1920 N. Forest Ave.  
  “Holidays at Leu Gardens returns featuring thousands of festive and vibrant poinsettias along with seasonal flowers and foliage to create a holiday themed garden. Additionally, guests can explore inside the historic Leu House where there will be a number of traditional holiday decorations adorning the home, as well as a special garden gnome scavenger hunt for the kids. These experiences are included with general admission. Purchase tickets by visiting leaugardens.org/holidays-at-leu-gardens.  This event includes Dazzling Nights, when Leu Gardens will transform once again into a stunning, winter wonderland featuring a million dazzling lights, shining forests, magical displays, music and beautiful sculptures during Dazzling Nights.” Purchase your tickets by visiting dazzlingorlando.com.  
  
• 2 p.m., its Shop Small Sip and Stroll at Audubon Park Garden District, at 2906 Corrine Drive  
  “Join Audubon Park Garden District as they celebrate Small Business Saturday with their Shop Small Sip and Stroll. Explore multiple stops throughout the Audubon Park Garden District, sipping on beverages, and supporting local businesses.”
  
• Thursday, Dec. 4 at 5 p.m., it’s Holiday on the Drive in College Park.   
  “The College Park Main Street District invites families and friends to Holiday on the Drive featuring Santa Claus, snow slide, live carolers, food trucks, carriage rides, arts and crafts, live music and more.” ” 
  
• Friday, Dec. 5 through Sunday, Dec. 21 from 5:30-9 p.m. daily, its the Holiday Train, North East Lawn of Lake Eola Park, 512 E. Washington St.  
  “The train will be running on the Northeast Lawn at Lake Eola Park on Friday, Saturday, and Sunday evenings. You can also experience snowfall in downtown Orlando this holiday season! Snow will fall on Washington St. by the Lake Eola House for 15 minutes on Friday, Saturday, and Sunday evenings beginning Friday, Dec. 5 at 6:15 p.m., 7:15 p.m., 8:15 p.m., 9:15 p.m.  
• Lake Eola Park will also host a Merry Market. Here, you’ll shop from local vendors with products ranging from soaps, candles, jewelry, and more! At Lake Eola, you can also visit the Grinch’s Lair. Stop by and snap a photo with everyone’s favorite Christmas crank. He’ll be spreading mischief (and maybe a little cheer) Fridays, Saturdays, and Sundays, December 5–21 from 5:30 to 9:30 p.m.” 
  
• Friday, Dec. 5 it’s the City of Orlando Annual Tree Lighting Celebration, with festivities starting at 5 p.m. and the Tree Lighting ceremony at 8 p.m. at Lake Eola Park. 
  “The highlight of the event is the lighting of the 64-foot Christmas tree featuring 88,000 animated lights. The event will include holiday performances at the Walt Disney Amphitheater, food trucks and a holiday market on International Plaza at Lake Eola Park. You can also experience the magic of the “2811 Clemwood Street Lights,” near the Eola House. Originally a beloved neighborhood display, this touching tribute honors lives lost to COVID-19, thanks to the generous donation from former homeowners. At Lake Eola, you can also meet Santa at the Eola House every Friday, Saturday, and Sunday from 5:30 p.m.- 9:00 p.m. This is a free experience!” 
  
• Saturday, Dec. 6 at 2 p.m., it’s Light Up SoDo at Kimco’s SoDo Shopping Center, 35 West Crystal Lake St. 
  “The SoDo Main Street District’s annual family and pet-friendly holiday event will feature several activities including an appearance from Santa and Mrs. Claus, local vendors, delicious treats, musicians, surprise performers, children’s activities, face painting and more.” 
  
• Sunday, Dec. 7 at 2 p.m., its Krampusfest  at The Plaza Live, 425 N. Bumby Ave.  
  “The Milk District’s annual Krampusfest returns bringing the alpine spirit to Orlando. Until dark, families can enjoy live music, professional photography opportunities, local food, drink and retail vendors, the Krampuslauf parade and a costume contest. Once the sun sets, this event takes a spookier turn and while still family-friendly, is encouraged to be enjoyed by those 13 or older. ” 
  
• Wednesday, Dec. 10 at 6:30 p.m., its WinterFest at Lake Eola Amphitheater. 
  “The City of Orlando Families, Parks, and Recreation Department invite you to a night of singing, dancing, and fun at Let it Snow, Let it Groove. Then on Saturday, Dec. 13 at 7 p.m., it’s a Holiday Movie at Lake Eola Park.” 

• Saturday, Dec. 13 at 10 a.m., its Navidades en Gateway – Christmas in Gateway at
• Prince Peace Lutheran Church, 1515 S. Semoran Boulevard.  
• “Join Gateway District for Navidades en Gateway, a family-friendly event featuring live entertainment, holiday music, arts and crafts, food and drink, shopping, a kid’s zone, pictures with Santa, a puppeteer and much more.”  

• Saturday, Dec. 13 at 8 p.m., it’s the 12 Pubs of Christmas Pub Crawl starting at Ten10 Brewing, 1010 Virginia Drive.
  “Join Mills 50 District for their yearly pub crawl, featuring specials from your favorite Mills 50 local businesses and endless holiday cheer.” 
  
• Sunday, Dec. 14 from 5:30 – 7:30 p.m., it’s Sensory Night at Lake Eola Park.
• “Immerse yourself in the magic of the holidays in a sensory-friendly environment. We’ve curated an evening of joy and comfort for everyone, featuring:  
• No/Low Music: Enjoy the festive atmosphere without stimulating sounds.  
• Quiet Place: A serene space with water, snacks, and calming vibes.  
• Fidget Spinners: Engage and relax with tactile sensory tools.  
• Noise-Canceling Headphones: Find tranquility amidst the holiday cheer.  
• Santa Line System: A thoughtful approach to meet Santa with ease.  
• Train Ride Line System: Hop aboard the holiday train stress-free!  

That’s about it — and that’s a lot! So get out there and have some Christmas cheer and holiday fun – Orlando-style!

To learn more, visit orlando.gov/holidays and downtownorlando.com/holidays.   Happy holidays from all of us at Freeline Media!

Michael Freeman is an Orlando journalist, playwright, and author of the book A Christmas Eve Story. Contact him at Freelineorlando@gmail.com.

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