Tis the Season Event Schedule 2023

Tis the Season for Making Merry Memories

There's something magical in the air in downtown Winter Garden. You can just sense it as the sights and sounds of the season complement the small town charm of historic downtown. An abundance of festive decorations and light displays, including twinkle lit arches along the West Orange Trail in downtown's center, and carefully staged photo stations provide the perfect setting to create precious holiday memories. There are 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. On select dates (see Holiday Happenings Daily Event Schedule below), there are complimentary live music performances, projection light shows, street performers, and more that add to the festive Normal Rockwell-like ambiance of downtown.

Holiday Happenings Daily Event Schedule At-A-Glance (Historic Downtown Winter Garden):

The Holiday Happenings listed are inclusive of City of Winter Garden sponsored/co-sponsored events as well as additional holiday events presented by community organizations scheduled to take place in downtown Winter Garden. Events are subject to change. Please monitor the website regularly for any updates and additions to event schedule. Activities are FREE except for those noted that require a reservation/fee. The list is provided as a courtesy to the community to aid in making plans and merry memories. 

The annual signature City of Winter Garden sponsored/co-sponsored events are noted in bold.

November 9                 Jingle 'n' Mingle Late Night Shopping Fun hosted by participating merchants, Downtown, 5 - 8 pm
November 11              Craft Affair (Arts & Crafts Show), Jessie Brock Community Center, 10 am - 2 pm
November 18              Thanksgiving Celebration at the Winter Garden Farmers Market, Parking Garage Plaza, 8 am - 1 pm
November 22               Moonshine & Mistletoe Musical Live Theatre Preview Show, Garden Theatre, 7:30 pm (Purchase Ticket)
November 24               Moonshine & Mistletoe Musical Live Theatre Show, Garden Theatre, 7:30 pm (Purchase Ticket)
November 25              Small Business Saturday, Daylong -  LIVE MUSIC and Holiday Shopping Kickoff Love Local!
November 25               Moonshine & Mistletoe Musical Live Theatre Show, Garden Theatre, 2 pm and 7:30 pm (Purchase Ticket)
November 26               Moonshine & Mistletoe Musical Live Theatre Show, Garden Theatre, 2 pm and 6 pm (Purchase Ticket)
November 28               It's a Wonderful Life Classic Movie (1946, PG, 2 hr 10 min), Garden Theatre, 7 pm (Purchase Ticket)
November 29               Moonshine & Mistletoe Musical Live Theatre Show, Garden Theatre, 12:30 pm (Purchase Ticket)
November 30               Moonshine & Mistletoe Musical Live Theatre Show, Garden Theatre, 7:30 pm (Purchase Ticket)
December 1                 West Orange Ministerial Association presents "Sounds of Christmas," City Hall, 5:30 - 6 pm
December 1                 Light Up Winter Garden - 36th Annual, Historic Downtown, 6 - 9 pm
December 1                 “Christmas in the Garden" Big Band Concert featuring Charles Billingsley, First Baptist Church of Winter Garden,                                           6:30 pm
December 1                 Moonshine & Mistletoe Musical Live Theatre Show, Garden Theatre, 7:30 pm (Purchase Ticket)
December 2                 A Very Merry Farmers Market, Downtown Pavilion, 8 am - 1 pm
December 2                Winter Garden Christmas Parade, Historic Downtown, kickoff at 10 am
December 2                Holiday Market at Historic Downtown (pedestrian-only/streets closed), 1 - 4 pm
December 2                 Moonshine & Mistletoe Musical Live Theatre Show, Garden Theatre, 2 pm and 7:30 pm (Purchase Ticket)
December 2                 Create a Gingerbread House Holiday Family Event at SOBO Art Gallery, 4 -5:30 pm (Reservation/Fee Required)
December 2                Winter Garden Christmas Golf Cart Parade -- 11th Annual, Historic Downtown, 6 pm
December 2                A Merry Winter Garden Light Show at City Hall, 6 - 9 pm
December 2                 Strolling Performers & Live Entertainment, Historic Downtown, 6 - 9 pm
December 2                 Moonshine & Mistletoe Musical Live Theatre Show, Garden Theatre, 2 pm and 6 pm (Purchase Ticket)
December 3                 Horse Drawn Holiday Carriage Tours, Downtown Pavilion, 5:30 - 9:30 pm (Reservation/Fee Required)
December 3                 A Merry Winter Garden Light Show at City Hall, 6 - 9 pm
December 5                 Elf Classic Movie (2003, PG), Garden Theatre, 7 pm (Purchase Ticket)
December 6                 Moonshine & Mistletoe Musical Live Theatre Show, Garden Theatre, 7:30 pm (Purchase Ticket)
December 7                 Chanukah Celebration & Menorah Lighting by Chabad of South Orlando, Butterfly Sculpture Park, Time: TBD
December 7                 Moonshine & Mistletoe Musical Live Theatre Show, Garden Theatre, 7:30 pm (Purchase Ticket)
December 8                A Merry Winter Garden Light Show at City Hall, 6 - 9 pm
December 8                 Strolling Performers & Live Entertainment, Historic Downtown, 6 - 9 pm
December 8                Live Holiday Music by Roots & Rosin (Duo), Fridays on the Plaza, Historic Downtown, 7 - 9 pm
December 8                 Moonshine & Mistletoe Musical Live Theatre Show, Garden Theatre, 7:30 pm (Purchase Ticket)
December 9                Santa Visit at A Very Merry Farmers Market -- Santa 9 am - 12 pm (Parking Garage Plaza); Market: 8 - 1   
December 9                 Moonshine & Mistletoe Musical Live Theatre Show, Garden Theatre, 2 pm and 7:30 pm (Purchase Ticket)
December 9                A Merry Winter Garden Light Show at City Hall, 6 - 9 pm
December 9                 Strolling Performers & Live Entertainment, Historic Downtown, 6 - 9 pm
December 10               Moonshine & Mistletoe Musical Live Theatre Show, Garden Theatre, 2 pm and 6 pm (Purchase Ticket)
December 10               Horse Drawn Holiday Carriage Tours, Downtown Pavilion, 5:30 - 9:30 pm (Reservation/Fee Required)
December 10              A Merry Winter Garden Light Show at City Hall, 6 - 9 pm
December 12               Horse Drawn Holiday Carriage Tours, 5:30 - 9:30 pm (Reservation/Fee Required)
December 12               The Nightmare Before Christmas Classic Movie (1946, PG), Garden Theatre, 7 pm (Purchase Ticket)
December 13               Moonshine & Mistletoe Musical Live Theatre Show, Garden Theatre, 7:30 pm (Purchase Ticket)
December 14               Horse Drawn Holiday Carriage Tours, Downtown Pavilion, 5:30 to 9:30 pm (Reservation/Fee Required)
December 14               Moonshine & Mistletoe Musical Live Theatre Show, Garden Theatre, 7:30 pm (Purchase Ticket)
December 15               Cocoa & Cookies with Santa Preschool Holiday Program (Ages 3-5), Jessie Brock Comm Center, 10 am - 12 pm
December 15               Moonshine & Mistletoe Musical Live Theatre Show, Garden Theatre, 2 pm and 7:30 pm (Purchase Ticket)
December 15              A Merry Winter Garden Light Show at City Hall, 6 - 9 pm
December 15               Strolling Performers & Live Entertainment, Historic Downtown, 6 - 9 pm
December 15              Live Holiday Music by Paint it Black Quartet, Fridays on the Plaza, 7 - 9 pm
December 16              Santa Visit at A Very Merry Farmers Market -- Santa 9 am - 12 pm (Parking Garage Plaza); Market: 8 - 1   
December 16               Moonshine & Mistletoe Musical Live Theatre Show, Garden Theatre, 2 pm and 7:30 pm (Purchase Ticket)
December 16              A Merry Winter Garden Light Show at City Hall, 6 - 9 pm
December 16               Strolling Performers & Live Entertainment, Historic Downtown, 6 - 9 pm
December 16               Moonshine & Mistletoe Musical Live Theatre Show, Garden Theatre, 2 pm and 7:30 pm (Purchase Ticket)
December 17               Moonshine & Mistletoe Musical Live Theatre Show, Garden Theatre, 2 pm (Purchase Ticket)
December 17              A Merry Winter Garden Light Show at City Hall, 6 - 9 pm
December 17               Horse Drawn Holiday Carriage Tours, 5:30 - 9:30 pm (Reservation/Fee Required)
December 17               Orlando Choral Society: "The Many Moods of Christmas," First Baptist Church of Winter Garden, 6:30 pm
                                     (Admission: $10 each at door & toy donation per family)
December 18               Horse Drawn Holiday Carriage Tours, 5:30 - 9:30 pm (Reservation/Fee Required)
December 19               Horse Drawn Holiday Carriage Tours, 5:30 - 9:30 pm (Reservation/Fee Required)
December 20               Horse Drawn Holiday Carriage Tours, 5:30 - 9:30 pm (Reservation/Fee Required)
December 20               Moonshine & Mistletoe Musical Live Theatre Show, Garden Theatre, 7:30 pm (Purchase Ticket)
December 21               Horse Drawn Holiday Carriage Tours, 5:30 - 9:30 pm (Reservation/Fee Required)
December 21               Moonshine & Mistletoe Musical Live Theatre Show, Garden Theatre, 7:30 pm (Purchase Ticket)
December 22               Moonshine & Mistletoe Musical Live Theatre Show, Garden Theatre, 2 pm and 7:30 pm (Purchase Ticket)
December 22              A Merry Winter Garden Light Show at City Hall, 6 - 9 pm
December 22               Strolling Performers & Live Entertainment, 6 - 9 pm
December 22              Live Holiday Music by Dickens Carolers, Fridays on the Plaza, 7 - 9 pm
December 23               A Very Merry Farmers Market, 8 am - 1 pm
December 23               Moonshine & Mistletoe Musical Live Theatre Show, Garden Theatre, 2 pm (Purchase Ticket)
December 23              A Merry Winter Garden Light Show at City Hall, 6 - 9 pm
December 23               Strolling Performers & Live Entertainment, Historic Downtown, 6 - 9 pm
December 26               Horse Drawn Holiday Carriage Tours, 5:30 - 9:30 pm (Reservation/Fee Required)
December 27               Horse Drawn Holiday Carriage Tours, 5:30 - 9:30 pm (Reservation/Fee Required)
December 28               Horse Drawn Holiday Carriage Tours, 5:30 - 9:30 pm (Reservation/Fee Required)
December 29              Live Holiday Music by Gilly & The Girl (Duo), Fridays on the Plaza, 7 - 9 pm
December 30               A Very Merry Farmers Market, Downtown Pavilion, 8 am -1 pm

Holiday Events Descriptions (sponsored/co-sponsored by the City of Winter Garden)

All City of Winter Garden events are FREE except the Horse Drawn Holiday Carriage Tours.

Small Business Saturday at Downtown - LIVE MUSIC & FESTIVE FUN

Visit the downtown mom-and-pop stores to kick off your holiday shopping, and discover unique finds for your gift list when you shop on Small Business Saturday. Live musical entertainment will perform at Centennial Plaza from 12:00 pm to 8:00 pm, adding to downtown's merry ambiance as you shop, dine, and stroll through the festive streets. Remember to shop small to have a big impact!

Saturday, November 25, Daylong
Historic Downtown

Light Up Winter Garden - 36th Annual

Join us at the 36th annual Light Up Winter Garden to welcome the holiday season with this annual event. that includes live entertainment, holiday activities, and lots of fun. The lighting will take place at 6:15 pm at City Hall (300 W. Plant St.). The event kicks off the City of Winter Garden's 39 days of Tis the Season programming and decorations downtown. Sponsored by Duke Energy. (Downtown streets are closed for this event.)

Friday, December 1, 6:00 - 9:00 pm (Lighting at 6:15 pm)
Historic Downtown

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!
(Downtown streets are closed for this event.)

Saturday, December 2, 10:00 am
Historic Downtown

Holiday Market at Downtown

Downtown Winter Garden turns into a PEDESTRIAN-ONLY Holiday Market from 1:00 – 4:00 pm on Saturday, December 2. Leisurely stroll along the festive-adorned streets to enjoy the sights and sounds of the season while holiday shopping.

Go from booth-to-booth and 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!

(Downtown streets are closed for this event.)

Saturday, December 2, 1:00 - 4:00 pm
Historic Downtown

Winter Garden Christmas Golf Cart Parade - 11th Annual 

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.
(Downtown streets are closed for this event.)

Saturday, December 2, 6:00 pm
Historic Downtown

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. A Very Merry Winter Garden Light Show will be held for 10 nights this year so mark your calendars.

December 2, 3, 8, 9, 10, 15, 16, 17, 22, 23
6:00 - 9:00 pm
Winter Garden City Hall, 300 W. Plant Street

Strolling Holiday-Themed Performers & Live Entertainment

Be on the lookout on Friday and Saturday evenings (Dec. 1 - Dec. 23) from 6:00 to 9:00 pm for strolling live entertainment including holiday music and shows, as well as fun antics to delight all ages. 

December 1, 2, 15, 16, 22, 23
6:00 - 9:00 pm
Historic Downtown

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 3, 10, 12, 14, 17, 18, 19, 20, 21, 26, 27, 28
5:30 - 9:30 pm
Historic Downtown/Board Carriage at Downtown Pavilion,104 S. Lakeview Avenue

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 8 – Roots & Rosin Duo
December 15 – Paint It Black Quartet
December 22 – Safia Valines Trio
December 29 – Gilly & The Girl Duo

7:00 - 9:00 pm
Centennial Plaza, Historic Downtown

A Very Merry Winter Garden Farmers Market

Santa visits the market on Saturday, December 9 and 16 (9:00 am - 12:00 pm) to hear wish lists and pose for pictures (complimentary). On every Saturday in December, you can find fresh holiday bouquets and wreaths, holiday plants, seasonal decorations, great gifts, as well as fresh produce, baked goods, and artisan food to make your holidays gatherings festive, 

Saturdays, 8:00 am - 1:00 pm
Santa Visit: December 9 & 16, 9:00 am - 12:00 pm
Downtown Pavilion, 104 S. Lakeview Avenue 

Available All Day, Every Day for 38 Days in Historic Downtown (December 1, 2023, - January 7, 2024)

• Festive Decorations & Light Displays

  Historic downtown is turned into a Holiday Wonderland with festive displays and decorations throughout. At night, the downtown is aglow with twinkle-lit trees, lighted arches lining the West Orange Trail while color-lit splashes of water dance in the Downtown Interactive Fountain. The decorations and lights provide a magical backdrop to the holiday festivities.

• Holiday-Themed Photo Stations

  A number of holiday-themed photo stations are located throughout Downtown providing picture-perfect backdrops to preserve the holiday memory for holiday cards and social posts. See how many you can find. Hint: City Hall, Centennial Plaza, Police Station, Parking Garage, and more! 

• Holiday Music Fills the Downtown Air

• No air pods needed in downtown Winter Garden as holiday tunes can be heard throughout thanks to the piped in music coming from everywhere (even the rocks). Hum along or belt out your favorites while you stroll, shop, and dine in this Winter Garden Wonderland.

• It's a Wonderful Life in Winter Garden Holiday Art Exhibit, City Hall Art in Public Places Gallery

  As a holiday tribute, Crealdé School of Art and the Winter Garden Heritage Foundation partnered to curate an exhibition of photographs and paintings that celebrate the special character of the historic downtown district. This exhibit is sure to help you slow down, reminisce, and find the wonderful during this busy time of year. 

  November 1 - January 5: Monday - Friday, 7:30 am - 5:30 pm (excluding holiday closures):
  Nov. 1, 2, 3, 6, 7, 8, 9, 10, 13, 14, 15, 16, 17, 20, 21, 22, 27, 28, 29, 30
  Dec. 1, 4, 5, 6, 7, 8, 11, 12, 13, 14, 15, 18, 19, 20, 21, 22, 26, 27, 28, 29
  Jan. 2, 3, 4, 5

  Art in Public Places Gallery at Winter Garden City Hall, 300 W. Plant Street

Garden Theatre Holiday Programming

160 W. Plant Street

Holiday Live Theatre Show:
Moonshine & Mistletoe: An Appalachian Tale at the Garden Theatre

Moonshine & Mistletoe: An Appalachian Tale is a is a wholesome theatrical event to experience with the whole family this holiday season as it makes its World Premiere. The musical is a nod to a bygone era as the Ballard's celebrate Christmas with family friends during the Great Depression by sharing their love of Appalachian hymns and carols. Rated G.

November 24 - December 23
Click here to purchase tickets.

Holiday Movies:

It's a Wonderful Life Classic Movie (1946, PG, 2 hr 10 min), 7 pm, Purchase Ticket
Elf  Classic Movie (2003, PG, 1 hr 41 min), 7 pm. Purchase Ticket
The Nightmare Before Christmas Classic Movie (1946, PG, 2 hr 10 min), 7 pm. Purchase Ticket

Shopping

Downtown shops offer unique merchandise and great customer service to help you find that perfect gift. Find all that you need to make your holidays special from seasonal apparel and décor, festive outfits and accessories, to party essentials and decorations, gourmet provisions, and of course gift ideas galore! (Mark your calendar for the pedestrian-only outdoor Holiday Market on Saturday, December 2, 1 - 4 pm, for a fun shopping experience with complimentary holiday kids crafts, activities, and photo booths.)

Dining & Dessert -- Sweet Treats, Hot Chocolate, & More!

Create holiday memories with family and friends by dining under the twinkling stars and lights at the outdoor patios in historic downtown. Embrace the holiday charm by grabbing a hot chocolate, a spice latte, a caramel Boba tea, or your favorite beverage. Be sure to get a gingerbread cookie or holiday cupcake to go along with it. Or, perhaps some peppermint ice cream or chocolates will satisfy your craving. 

With a wide assortment of restaurants, cafes, bakeries, chocolate shops, and ice cream parlors, to choose from, there is something for everyone. Gather with friends and family to dine or grab to-go while enjoying the lights and festivities.

Citywide Holiday Programs & Activities

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 11 / North West Winter Garden
Tuesday, December 12 / North East Winter Garden
Wednesday, December 13 / South Winter Garden: West CR 545 Corridor
Thursday, December 14 / South Winter Garden: East CR 545 Corridor
Friday, December 15 / South Winter Garden: CR 535 and Daniel’s Road Corridor
Saturday, December 16 / South Winter Garden: Beulah and Windermere Road Corridor

Alternate date is December 18 if weather interrupts one of the visits

Please stay tuned to the posting of Santa's Route Maps. Once posted, 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!

Contest categories are Best Overall, Best Theme, Most Original, and Best Apartment or Townhome. The Best Overall winner is awarded $100, and prizes are awarded in each category: 1st place winners: $75 and 2nd place winners: $50. And, of course, bragging rights! 

Judging takes place on Tuesday, December 12, and Wednesday, December 13, 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 to complete and submit the De-Light-Ful Decorations Entry form by December 8, 2023.. Entry forms must be received no later than Friday, December 8, 2023. 

For questions or to obtain a hard copy of the entry form, please call 407.656.4155.

Holiday Gifts for Kids Program hosted by WGPAL- Accepting Donations

The Winter Garden Police Athletic League, Inc. (WGPAL) 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, sport balls, arts & crafts kits, puzzles, action figures, jewelry kits, remote control vehicles, matchbox cars, infant toys,  bicycles for all ages,, gift card, etc. to this community initiative. Donations are tax deductible. Donation drop-off is November 1 - December 8 to the Winter Garden Police Department, 251 W. Plant Street. 

Registration for City of Winter Garden families in need is open November 20 - December 1. Click here for details and registration. Questions, call 407.656.3636 ext. 5416.