Tis the Season Schedule 2021

December is Tis the Season to Make Memories

Light Up Winter Garden and the Winter Garden Christmas Parade will be held in 2021. The City’s elves have built a holiday wonderland for our community that will be fun and safe for everyone to enjoy. Downtown Winter Garden is aglow with festive lighting and decorations, holiday-themed photo locations, painted holiday mural wall, Winter Wonderland Maze, and a host of outdoor seasonal activities for all ages!  

All activities are free except for those noted that require reservations

November 20              City of Winter Garden Annual Craft Affair, 10 am to 2 pm

November 27              Shop Small Business Saturday - Kick start your holiday shopping 

November 27              Small Business Saturday Downtown Sidewalk Sale -- All Day

November 27              Holiday Movie at the Pavilion -- The Polar Express (2004, G), 5:30 pm pre-movie activities, 7:10 pm movie

December 3                Light Up Winter Garden, 6 to 9 pm

December 3                First Baptist Holiday Concert on the steps of Winter Garden First Baptist Church, 6:30 pm

December 4                A Very Merry Farmers Market, 8 am to 1 pm

December 4                Winter Garden Christmas Parade, starts at 10 am

December 4                Make a Gingerbread House at SOBO Art Gallery, 4 to 5:30 pm (Reservation/Fee Required)  SOLD OUT

December 4                Horse Drawn Holiday Carriage Tours, 5:30 to 9:30 pm  (Reservation/Fee Required)

December 4                A Merry Winter Garden Light Show at City Hall, 6 to 9 pm      

December 5                The Muppet Christmas Carol (1992, G) Interactive Movie, Preshow 6:30 pm, Movie 7:00 pm. (Tickets Required)

December 9                Holiday Boutique Stroll -- shops of Historic Downtown, 5 to 8 pm 

December 10              Fridays on the Plaza Holiday Music - Roots & Rosin, 7 to 9 pm

December 10              A Merry Winter Garden Light Show at City Hall, 6 to 9 pm 

December 10              Horse Drawn Holiday Carriage Tours, 5:30 to 9:30 pm  (Reservation/Fee Required)

December 11               A Very Merry Farmers Market, 8 am to 1 pm

December 11              A Merry Winter Garden Light Show at City Hall, 6 to 9 pm

December 11              Horse Drawn Holiday Carriage Tours and Holiday Music, 5:30 to 9:30 pm  (Reservation/Fee Required)

December 12              Garden Choir's Holiday Concert at the Garden Theatre (Details: TBA)

December 12              A Merry Winter Garden Light Show at City Hall, 6 to 9 pm

December 12              Holiday Golf Cart Parade, starts at 5:30 pm at Dr. Bradford Memorial Park and continues through Downtown

December 17             Fridays on the Plaza Holiday Music -  The Caroling Company, 7 to 9 pm

December 17              Horse Drawn Holiday Carriage Tours, 5:30 to 9:30 pm (Reservation/Fee Required)

December 17              A Merry Winter Garden Light Show at City Hall, 6 to 9 pm

December 18              A Very Merry Farmers Market, 8 am to 1 pm

December 18              Annual Santa Bike Ride hosted by Winter Garden Wheel Works: 3 to 5 pm Refreshments/Photos, 6 pm Bike Ride

December 18             Horse Drawn Holiday Carriage Tours, 5:30 to 9:30 pm (Reservation/Fee Required)

December 18              A Merry Winter Garden Light Show at City Hall, 6 to 9 pm

December 18              Street Holiday Entertainment with Jugglers, 6 to 9 pm

December 19              A Merry Winter Garden Light Show at City Hall, 6 to 9 pm

December 20              Horse Drawn Holiday Carriage Tours, 5:30 to 9:30 pm

December 22              Horse Drawn Holiday Carriage Tours, 5:30 to 9:30 pm  (Reservation/Fee Required)

December 23              A Merry Winter Garden Light Show at City Hall, 6 to 9 pm 

December 23              Horse Drawn Holiday Carriage Tours, 5:30 to 9:30 pm (Reservation/Fee Required)

December 24              Horse Drawn Holiday Carriage Tours, 5:30 to 9:30 pm (Reservation/Fee Required)

December 26              Horse Drawn Holiday Carriage Tours, 5:30 to 9:30 pm  (Reservation/Fee Required)

December 27              Horse Drawn Holiday Carriage Tours, 5:30 to 9:30 pm  (Reservation/Fee Required)

December 28              Horse Drawn Holiday Carriage Tours, 5:30 to 9:30 pm  (Reservation/Fee Required)

December 29              Horse Drawn Holiday Carriage Tours, 5:30 to 9:30 pm  (Reservation/Fee Required)

December 30              Horse Drawn Holiday Carriage Tours, 5:30 to 9:30 pm  (Reservation/Fee Required)

December 31             Pilars - New Year's Eve Pilars Perfect Jazz Band, 8:30 pm to 12:30 am

All scheduled events are tentative and may be canceled pending COVID-19 restrictions and mandates. Please remember to be safe this holiday season as you make special memories.  

Downtown is  transformed into a Winter Wonderland through January 9, 2022, with the sights and sounds of the season for all ages to enjoy including festive light displays and decorations, holiday music, and colorful Downtown Interactive Fountain.

More Holiday Fun in Downtown Winter Garden:

Winter Wonderland Maze at City Hall, 300 w. Plant Street. Find your way through the enchanted maze of holiday décor and glistening lights and uncover the themed photo spots inside to capture fun memories.

Holiday Mural Wall @ 49 S. Main St, and Holiday-Themed Photo Locations throughout Downtown for picture perfect holiday cards and social posts.

Strolling Holiday-Themed Performers -- be on the lookout on Friday and Saturday evenings (Dec. 3-18) from 6 to 9 pm for pop-up street performers to delight all ages.

A Very Merry Winter Garden Farmers Market on Saturdays - December 4, 11, and 18 -- 8:00 am to 1:00 pm. Find flowers and wreaths, holiday plants, seasonal decorations, the freshest produce and artisan food to make your holidays festive, as well as great gifts! (Due to the holiday, a Farmers Market will NOT be held on December 25 and January 1.)

Garden Theatre – Live Production:

Big, The Musical - live theatre, November 19-December 10. Click here to purchase tickets.

Holiday Shopping -- seasonal merchandise, food & drinks at unique shops and restaurants

Holiday Dining -- expansive Outdoor Patios throughout downtown for dining under the stars and festive lights and a host of fine dining and casual eateries for a special holiday get together

Holiday Spirit Extends Beyond Downtown:

Santa Run

Winter Garden Fire Rescue’s annual “Santa Run” brings Santa and his sleigh through City neighborhoods. The moving parade takes place between 5:45-9:00 pm each as Santa, along with his firefighter, police, and city helpers spread holiday cheer, music, and treats along the way.

Santa Run Schedule:

Monday, Dec. 13/North West Winter Garden

Tuesday, Dec. 14/ North East Winter Garden

Wednesday, Dec. 15/South Winter Garden: West CR 545 Corridor

Thursday, Dec. 16/South Winter Garden: East CR 545 Corridor

Friday, Dec. 17/South Winter Garden: CR 535 and Daniel’s Road Corridor

Saturday, Dec. 18/South Winter Garden: Beulah and Windermere Road Corridor

Alternate date is December 20 if weather interrupts one of the visits.

Please check Santa's nightly route map to see the estimated time of Santa’s arrival and/or to find a location near you to go see Santa’s parade. (Due to significant growth of Winter Garden, not all neighborhoods or streets can be accommodated.) Maps will be posted as soon as received from the North Pole.

Due to safety concerns, please refrain from parking on the street during your neighborhood’s Santa Run. Street parking, especially parking on both sides of street, may prohibit the parade from going down a street. 

 De-Light-Ful Decorations Contest

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!

Judging takes place on Tuesday, December 14, and Wednesday, December 15, starting at 5:30 pm. Winners will be notified by phone on December 16.

Hosted by Winter Garden Parks & Recreation, the contest is free to enter and all homes must be within city limits.

Click here for entry form and instructions on how to submit.

Tis the Season 2021 flyer

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