Tis the Season Schedule 2022
December is Tis the Season to Make Memories
Downtown is transformed into a Winter Wonderland for 38 days from December 2, 2022, through January 8, 2023. Special events, live entertainment, festive light displays and decorations, themed photo stations and mural, holiday music, colorful Downtown Interactive Fountain, holiday-themed art exhibit, and more for all ages to enjoy.
Holiday Event Calendar
November 2 Tis the Season Wine Down Wednesday (hosted by Downtown Shops), 5 to 8 pm
November 12 Craft Affair Show
Tis the Season Events
All events are FREE except the carriage tours.
Light Up Winter Garden
Join us at Light Up Winter Garden to welcome the holiday season with this annual event to kick off our 38 days of Tis the Season. The lighting will take place at 6:15 pm at City Hall (300 W. Plant St.), followed by various activities for all to enjoy. Take the kids to see snow at the Main Street Wonderland (on South Main Street) featuring a snow slide and 22 tons of snow! Duke Energy, West Orange Ministerial Association, and the City of Winter Garden sponsor the event.
Friday, December 2, 6:00 - 9:00 pm (Lighting at 6:15 pm)
Winter Garden Christmas Parade
Bring a lawn chair or blanket and head to your favorite viewing spot for this long-standing Winter Garden holiday tradition. The Winter Garden Christmas Parade kicks off on Dillard Street at the Palmetto Street intersection (by Wells Fargo) proceeds north on Dillard Street, then heads west/left on Plant Street through historic downtown and concludes at Park Avenue. Do not forget to look for the Big Guy himself at the end of the parade!
Saturday, December 3, 10:00 am
Christmas Market on Plant Street
Downtown Winter Garden turns into a PEDESTRIAN-ONLY Christmas Market from 1:00 – 5:00 pm on Saturday, December 3. It is the perfect opportunity to enjoy the sights and sounds of the season without cars or traffic.
Leisurely stroll the outdoor market along the festive-adorned streets with holiday music filling the air. There will be special live music performances playing favorite holiday tunes at the Centennial Plaza gazebo throughout the hours of the Christmas Market.
Live Music Schedule:
1:00 - 3:00 pm Big Ron Betts Duo
3:45-5:45 pm BleWayle Duo
Go from shop-to-shop to find the perfect gifts. Stop and pose for pictures at the many festive backdrops and at the holiday-themed photo stations. Perfect atmosphere for grabbing a hot chocolate to sip as you stroll!
Saturday, December 3, 1:00 - 5:00 pm
10th Annual Winter Garden Christmas Golf Cart Parade
A holiday parade of elaborately-decorated golf carts through Downtown. Grab a viewing spot and be ready to be amazed. Hosted by West Orange Junior Service League and the City of Winter Garden. Reservation/fee required for golf cart participation.
Saturday, December 3, 6:00 pm
A Very Merry Winter Garden Light Show
This annual animated holiday light extravaganza has become a holiday tradition to so many households. The front façade of Winter Garden City Hall (300 W. Plant St.) becomes the canvas for this spectacular show synchronized to music. The 25-minute display runs in a continuous loop from 6-9 pm
December 3, 4, 9, 10, 11, 16, 17, 18, 23
Strolling Holiday-Themed Performers
Be on the lookout on Friday and Saturday evenings (Dec. 2-17) from 6:00 to 9:00 pm for pop-up street performers to delight all ages.
Horse Drawn Holiday Carriage Tours
Right out of a Hallmark movie, SOUL Haven Ranch is offering 20-minute horse drawn carriage tour experiences through festive downtown Winter Garden on select nights throughout the month. The tours are available from 5:30 – 9:30 pm. Step into the carriage at the Downtown Pavilion (104 S. Lakeview Ave.) and enter a fairy tale adventure as you wind through the festive sights and sounds of downtown. Reservation/fee required.
December 4, 5, 6, 7, 11, 12, 13, 14, 18, 19, 20, 21, 26, 27, 28
Holiday Boutique Stroll
Stroll from shop-to-shop in the historic downtown winter wonderland for an evening of sips, snacks, and shopping. Invite your friends and family to the Holiday Boutique Stroll to create a festive memory while checking items off your gift list. Participating shops will host light refreshments, in-store raffles, and outdoor and indoor specials.
Thursday, December 8, 5:00 - 8:00 pm
Holiday Fridays on the Plaza
Live holiday music will fill the downtown air every Friday evening in December. The concerts are from 7:00 - 9:00 pm at the Centennial Plaza gazebo in the center of historic downtown.
December 9 – Safia Valines (Quartet)
December 16 – L & G Live
December 23 – Red Mint
December 30 – Ranahan
More FREE Holiday Fun in Downtown Winter Garden:
Magical Spirit in the Air
There's something magical in the air in downtown. You can just sense it as the sights and sounds of the season resonate alongside the historic charm! An abundance of festive decorations and light displays, including twinkle lit arches along the West Orange Trail in the downtown's center. Holiday tunes to hum along to as you stroll courtesy of the centralized sound system. Colorful bursts of water playfully spurt from the Downtown Interactive Fountain. Carefully staged photo stations provide the perfect setting to capture precious holiday memories. On select dates, complimentary live music performances, projection light shows, street performers, and more add to the festive ambiance that feels straight out of a Norman Rockwell painting.
Holidays in Winter Garden Art Exhibit, City Hall Art in Public Places Gallery
Local artists' creations depicting November and December holidays in Winter Garden (November 1 - December 30) at this special AIPP exhibit. The exhibit is open during regular City Hall hours, Monday - Friday, 7:30 am - 5:30 pm. Art in Public Places Gallery at City Hall, 300 W. Plant Street
Holiday-Themed Photo Locations
Located throughout Downtown for picture perfect holiday cards and social posts. See how many you can find. Hints: City Hall, Centennial Plaza, Police Station, Parking Garage, and more! Be sure to include the custom-painted holiday mural on the corner of S. Main Street and W. Plant Street. This year, the mural is larger and lit with lights.
A Very Merry Winter Garden Farmers Market
On every Saturday in December (December 3, 10, 17, 24, 31), 8:00 am to 1:00 pm. Santa visits the market on Saturday, December 10 and 17 (9:00 am - 12:00 pm) to hear wish lists and pose for pictures (complimentary). Find fresh holiday bouquets and wreaths, holiday plants, seasonal decorations, fresh produce and artisan food to make your holidays gatherings festive, as well as great gifts!
Saturdays, 8:00 am - 1:00 pm / Downtown Pavilion, 104 S. Lakeview Avenue (Note: On December 3, the Market is open until 2:00 pm)
Santa Visits: December 10 & 17, 9:00 am - 12:00 pm
Visit SOBO Art Gallery Artisans Appeal fun holiday show (November 25 - January 28), as well as the temporary and permanent exhibits at Winter Garden Heritage Museum. At the Central Florida Railroad Museum, There is a special presentation by a Disney Legend on Saturday, December 17, as well as the amazing railroad artifacts and working train display to see.
The Garden Theatre is hosting three holiday movies.
The community is invited to a FREE showing of Home Alone (1990/PG) on Saturday, December 3, at 2:00 pm. No ticket/reservation required.
The Garden Theatre will be showing Miracle on 34th Street (1947/NR) on Sunday, December 4 at 2:00 pm. The ticket price is $7.00 and a reservation is required.
The Garden Theatre will be showing Elf (the movie) (2003/PG) on Saturday, December 10 at 2:00 pm. The ticket price is $7.00 and a reservation is required.
Shopping & Dining in Festive Historic Charm
Downtown shops offer unique merchandise and great customer service to help find that perfect gift. Find all that you need to make your holidays special: seasonal apparel and décor, festive outfits and accessories, party essentials and decorations, gourmet provisions, and of course gift ideas galore! Mark your calendar for the Holiday Boutique Stroll on Thursday, December 8, 5:00 - 8:00 pm, for a fun holiday shopping experience.
Expansive Outdoor Patios throughout downtown for dining under the festive lights and stars, as well as a vast selection of casual eateries, fine dining, bakeries, ice cream parlors, and coffee houses for holiday gatherings with family and friends.
Holiday Spirit Extends Beyond Downtown:
Winter Garden Fire Rescue Annual 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 night as Santa, along with his elves (firefighter, police, and city helpers) spread holiday cheer, music, and treats along the way.
Santa Run Schedule:
Monday, December 12 / North West Winter Garden
Tuesday, December 13 / North East Winter Garden
Wednesday, December 14 / South Winter Garden: West CR 545 Corridor
Thursday, December 15 / South Winter Garden: East CR 545 Corridor
Friday, December 16 / South Winter Garden: CR 535 and Daniel’s Road Corridor
Saturday, December 17 / South Winter Garden: Beulah and Windermere Road Corridor
Santa Route Maps COMING SOON.
Alternate date is December 19 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.)
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
It is time to drag out the lights, hang up the garland, put up the glowing Santa, and enter your home in the annual De-Light-Ful Decorations contest! First and second place winners are awarded in each of three categories in addition to one overall winner. Festive presentations of outdoor decorations could win up to $100!
Judging takes place on Tuesday, December 13, and Wednesday, December 14, starting at 5:30 pm. Winners will be notified by phone on Friday, 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. Entry forms must be received no later than Friday, December 9, 2022.
For questions or to obtain a hard copy of the entry form, please call 407.656.4155.