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, holiday music, colorful Downtown Interactive Fountain, holiday-themed art exhibit, and more for all ages to enjoy.

All activities are free except for those noted that require reservations

To download a Tis the Season event schedule flyer, click here

Holiday Event Calendar

November 2                Tis the Season Wine Down Wednesday (hosted by Downtown Shops), 5 to 8 pm

November 12              Craft Affair Show, Jessie Brock Community Center, 10 am to 2 pm

November 26              Small Business Saturday  - Kick start your holiday shopping by supporting local small businesses

November 26              Small Business Saturday Downtown Sidewalk Sale -- All Day

December 2                Light Up Winter Garden, 6 to 9 pm

December 2                "A Big Band Christmas" concert at First Baptist Holiday Concert, 6:30 to 8:30 pm

December 3                A Very Merry Farmers Market, 8 am to 2 pm (extended hours)

December 3                Winter Garden Christmas Parade, starts at 10 am

December 3                Home Alone movie at the Garden Theatre, 160 W. Plant Street. 2 pm (Free admission/no ticket required)

December 3                Christmas Market on Plant Street with live holiday music, 1 to 5 pm

December 3                Make a Gingerbread House at SOBO Art Gallery, 1:30 to 3 pm (Reservation/Fee Required)

December 3                10th Annual Winter Garden Christmas Golf Cart Parade, 6 pm

December 3                A Merry Winter Garden Light Show at City Hall, 6 to 9 pm    

December 4                Miracle on 34th Street movie at the Garden Theatre,160 W. Plant Street, 2 pm (Reservation/Fee Required)

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

December 6               Horse Drawn Holiday Carriage Tours, 5:30 to 9:30 pm  (Reservation/Fee Required)

December 7               Horse Drawn Holiday Carriage Tours, 5:30 to 9:30 pm  (Reservation/Fee Required)

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

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

December 9               Live Holiday Music performed by Safia Valines Quartet, Fridays on the Plaza, 7 to 9 pm

December 10             A Very Merry Farmers Market, 8 am to 1 pm / Santa visits 9 am to 12:00 pm

December 10             Elf (the movie) at the Garden Theatre, 2 pm, 160 W, Plant St., (Reservation/fee Required)

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

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

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

December 12              Horse Drawn Holiday Carriage Tours, 5:30 to 9:30 pm  (Reservation/Fee Required)

December 13              Horse Drawn Holiday Carriage Tours, 5:30 to 9:30 pm  (Reservation/Fee Required)

December 14              Horse Drawn Holiday Carriage Tours, 5:30 to 9:30 pm  (Reservation/Fee Required)

December 16              A Merry Winter Garden Light Show at City Hall, 6 to 9 pm

December 16              Live Holiday Music by L & G Live, Fridays on the Plaza, 7 to 9 pm

December 17              A Very Merry Farmers Market, 8 am to 1 pm / Santa visits 9 am to 12:00 pm 

December 17              Railroad Museum Hosts Special Presentation by Disney Legend Tom Nabbe 

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

December 18              Horse Drawn Holiday Carriage Tours, 5:30 to 9:30 pm

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

December 19              Horse Drawn Holiday Carriage Tours, 5:30 to 9:30 pm  (Reservation/Fee Required)

December 19              Hanukkah Celebration & Menorah Lighting, outside of Downtown Post Office, 6 pm

December 20              Horse Drawn Holiday Carriage Tours, 5:30 to 9:30 pm  (Reservation/Fee Required)

December 21              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             Live Holiday Music by Red Mint, Fridays on the Plaza, 7 to 9 pm

December 24              A Very Merry Farmers Market, 8 am to 1 pm

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 30              Live Holiday Music by Ranahan, Fridays on the Plaza, 7 to 9 pm

December 31               A Very Merry Farmers Market, 8 am to 1 pm

Please monitor the website for any changes to event schedule.

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!

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

Cultural Exhibits

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, and the amazing railroad artifacts at the Central Florida Railroad Museum.

Garden Theatre

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

Holiday Shopping 

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.

Holiday Dining

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.

Holiday Gifts for Kids Program - Accepting Donations

The Winter Garden Police Athletic League, Inc. annually conducts a toy drive to provide holiday presents to Winter Garden youth (newborn-12 years old) in need. Please consider donating new toys, dolls, Legos, board games, arts & crafts kits, sport balls, etc. to this community initiative. Donations are tax deductible. Donation drop-off is November 1 - December 9 to the Winter Garden Police Department, 251 W. Plant Street. 

Registration for City of Winter Garden families in need is open October 24 - December 5. Click here for details and registration. Questions, call 407.656.3636 ext. 5416.

Christmas Tree Lot in Historic Downtown

Santa’s Old Fashioned Christmas Tees returns to historic downtown this year with its tent of fresh Fraser Fir trees, wreaths, and holiday décor available for sale at the corner of Plant and Dillard Streets, 114 E. Plant Street. Guests can also take photos and write a letter to Santa Claus.