Winter Garden Holiday Festivities

Merry Winter Garden Light Show

December 7, 2018 

6:00 PM -  9:00 PM  

City Hall

Holiday Music

December 7, 2018 

7:00 PM - 9:00 PM  

Centennial Plaza Gazebo

A Very Merry Farmers Market (with Santa)

December 8, 2018

9:00 AM - 2:00 PM

Merry Winter Garden Light Show

December 8, 2018 

6:00 PM -  9:00 PM  

City Hall

Holiday Carriage Rides

December 8, 2018

5:00 PM - 9:30 PM  

Downtown Winter Garden Pavilion

Take a horse-drawn carriage ride through festive downtown Winter Garden. Rides will commence every 15 minutes beginning at 5:00 pm on December 8, 15, and 22. Reservations and payment are required. Space is limited.

Book Online

Old-Fashioned Hayride with Santa

December 8, 2018

6:00 PM - 9:00 PM  

Downtown Winter Garden Pavilion

Join Santa on his sleigh for an old-fashioned hayride through downtown Winter Garden! Rides commence every 30 minutes starting at 6 pm.

Please call 407-656-4111 to make reservations. Space is limited

Santa Run Day 1: North West Winter Garden

December 10, 2018

5:45 PM - 9:00 PM

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Santa Run Day 2: North East Winter Garden

December 11, 2018

5:45 PM - 9:00 PM

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Santa Run Day 3: South Winter Garden, CR 545 Corridor (West Side)

December 12, 2018

5:45 PM - 9:00 PM

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Santa Run Day 4: South Winter Garden, CR 545 Corridor (East Side)

December 13, 2018 

5:45 PM - 9:00 PM

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Santa Run Day 5: South Winter Garden, CR 535 / Daniel's Road Corridor

December 14, 2018

5:45 PM - 9:00 PM

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Holiday Music

December 14, 2018 

7:00 PM - 9:00 PM  

Centennial Plaza Gazebo

A Very Merry Farmers Market (with Santa)

December 15, 2018

9:00 AM - 2:00 PM

Holiday Carriage Rides

December 15, 2018

5:00 PM - 9:30 PM 

Downtown Winter Garden Pavilion

Take a horse-drawn carriage ride through festive downtown Winter Garden. Rides will commence every 15 minutes beginning at 5:00 pm on December 8, 15, and 22. Reservations and payment are required. Space is limited.

Book online

Santa Run Day 6: South Winter Garden, Beulah / Windermere Road

December 15, 2018

5:45 PM - 9:00 PM

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Holiday Movie Night

December 15, 2018

6:00 PM - 8:30 PM 

Downtown Winter Garden Pavilion

Bring a blanket or chair and enjoy viewing The Polar Express under the stars in downtown Winter Garden! Dickens-era Carolers will perform a pre-show of holiday tunes at 6:00 pm. Movie showtime is 6:30 pm and the event is free!

Merry Winter Garden Light Show

December 15, 2018 

6:00 PM -  9:00 PM  

City Hall

Winter Garden Christmas Golf Cart Parade

December 16, 2018

5:30 PM - 7:00 PM

Please bring a lawn chair and come out to this great holiday community event to see over 100 festive golf carts parade through Downtown Winter Garden! To learn more about the event and route, please click on more details.

More Details

De-Light-Ful Decorations

December 18, 2018

5:30 PM - 8:30 PM

Drag out the lights, hang up the garland, put up the glowing Santa and enter your home to win! Festive presentations of outdoor decorations could win up to $100!

De-Light-Ful Decorations

December 19, 2018

5:30 PM - 8:30 PM

Drag out the lights, hang up the garland, put up the glowing Santa and enter your home to win! Festive presentations of outdoor decorations could win up to $100!

Holiday Music

December 21, 2018 

7:00 PM - 9:00 PM  

Centennial Plaza Gazebo

A Very Merry Farmers Market (with Santa)

December 22, 2018

9:00 AM - 2:00 PM

Holiday Carriage Rides

December 22, 2018 

5:00 PM - 9:30 PM  

Downtown Winter Garden Pavilion

Take a horse-drawn carriage ride through festive downtown Winter Garden. Rides will commence every 15 minutes beginning at 5:00 pm on December 8, 15, and 22. Reservations and payment are required. Space is limited.

Completely Booked

Merry Winter Garden Light Show

December 22, 2018 

6:00 PM -  9:00 PM  

City Hall

Holiday Music

December 28, 2018 

7:00 PM - 9:00 PM  

Centennial Plaza Gazebo

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