Dec 5

6 - 9 PM

tree lighting at 6:16PM

Downtown Winter Garden

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Join us for the momentous flipping of the switch to turn on the holiday lights and watch downtown glow. Enjoy holiday activities and entertainment.

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Dec 6

1:30PM - 3PM

Great Scott Farms

Mount Dora, FL​

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Come decorate 6 nostaglic farm-themed cookies during this 1.5 hour cookie decorating class!

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Dec 6

6:30PM - 8PM

Downtown Winter Garden

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Catch a trolley from the Holiday Night Market to nearby Main Street Holiday Stroll, an immersive holiday experience with festive scenery and ideal photo spots.

Trolley Stops:

• S. Woodland St. and E. Joiner St. (Rainbow Parking Lot)

• S. Main St. & W. Joiner St. (Main Street Holiday Stroll)

• S. Boyd Street & Tremaine St. (Holiday Night Market)

Please note: Trolleys are part of the event experience and are not the same as the shuttles transporting guests from remote parking areas.

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Multiple Dates

6 - 9PM

Dec 5-7, 12-14, 19-21, 26, 27

Downtown Winter Garden

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Be on the look out for strolling performers & live entertainment throughout downtown Winter Garden.

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Dec 17

6:30PM - 8:30PM

Island Touch Cafe

Ocoee, Florida

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3 round layers of pre-baked cakes, candy melts (for his big red nose, antlers, and Christmas lights), 2 large icing bags, dowels to hold your cake together, and decorations to personalize your cake which you'll be able to take home with you after class.

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Dec 22

2PM & 8PM

Garden Theatre

Winter Garden, FL 34787

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Celebrate the true Spirit of Christmas with this splendid show, filled with haunting special effects and an enormous dose of laughter. The touring production of A Christmas Carol is delightful and thoroughly entertaining, the perfect Winter Garden holiday event for all.

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(Reservation/Fee Required)

Dec 12 3PM - 9PM

Dec 13 10AM - 4PM

7000 Winegard Rd
Orlando, FL 32809

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Experience the best of Korean culture with authentic food, unique vendors, traditional games, K-pop and cultural performances, and a Hanbok experience. Free admission for a day of fun and celebration!

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Dec 13

3PM - 4:30PM

SOBO Winter Garden

 

Build a gingerbread house w/step by step instruction. $52 per house.

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(Reservation/Ticket Required)

Dec 20

5PM - 8PM

Clermont Historic Downtown

Sommer Sports

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A festive holiday night run/walk through Historic Downtown Clermont and along the beautiful Clermont waterfront.

 

Super cool finisher medal and long-sleeve shirt, chip timing, glow necklaces, costume prizes, and hot chocolate, and cookies will be waiting for you after you finish!

 

(Registration/Ticket Required)

Dec 5 - 4

6 - 9 PM

tree lighting at 6:16PM

Downtown Winter Garden

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The Main Street Holiday Stroll is an immersive holiday experience that will put the jolly in everyone's step. Stroll through the outdoor, picturesque, season-long display open every day.

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Dec 6

4 - 8PM

Downtown Winter Garden

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The Holiday Night Market transforms the Downtown Pavilion area to a picturesque festive open-air market bustling with market stalls of vendor booths of holiday goods for sale such as décor, unique gifts, festive treats and beverages, and more.

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Dec 6

6PM

Downtown Winter Garden

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Junior Service League and the CITY OF WINTER GARDEN will host the 13th Annual WG Christmas Golf Cart Parade.​

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Multiple Dates

6PM - 9PM

Dec 5-7, 12-14, 19-21, 26, 27
Winter Garden City Hall

300 W. Plant Street

Winter Garden, FL 34787

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This annual animated holiday light extravaganza is a town tradition!

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Multiple Dates
5:30 - 9:30PM​​

Downtown Pavilion

104 S. Lakeview Ave
Winter Garden, FL 34787

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Experience the magic of the holiday season with a private horse drawn carriage tour through Historic Downtown Winter Garden.

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(Reservation/Fee Required)

Fridays
7 - 9PM

Downtown Winter Garden

Centennial Plaza Gazebo

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• Dec 12- Dickens Carolers 

• Dec 19- Mistletones 

• Dec 26- Paul Q-Pek

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Dec 18

5PM - 8PM

Downtown Winter Garden

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After hours shopping at participating Downtown WG Merchants, from 5-8 pm.

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Dec 19

Gymnastic USA

13175 W. Colonial Dr

Winter Garden FL, 34787

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Gymnastics USA partnered with We Are Winter Garden to bring the community a night of Food Trucks, Santa Visit, WHOLE Family Open Gym, Winter Garden Vendors, Rock Climbing, DJ Music, Raffles & Prizes, Winter Garden Swag, Snow Fall, CHRISTMAS, and More!

 

Registration is required to enter. Get your free tickets on the Winter Garden App.

coming soon

Free Tickets

Multiple Dates

Dec 6, 13, 20, 27

8AM - 1PM

Downtown Pavilion

104 S. Lakeview Ave
Winter Garden, FL 34787

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This festive-decorated market is ideal for shopping for gifts, seasonal decor, as well as fresh product and artisan foods for your holiday celebrations.

 

Jolly Fellow will be visiting Dec 13th & 20th.

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Dec 6

6:30PM - 8PM

Downtown Winter Garden

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We have received word that Santa Claus is traveling from the North Pole to the market to see his Winter Garden friends. Visit with Santa (6:30 - 8:00 pm) to share your wish list and pose for photos. Free!

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Dec 6

6 - 9 PM

Home State Brewing Co.
Winter Garden, FL

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 Stroll through 15+ vendors for unique holiday finds, explore the book fair by White Rose Book Shop on the patio, meet local authors, & enjoy live music by Francesca in the Biergarten.

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Dec 7, 9, 11, 14, 16, 23

at the Garden

160 W Plant Street
Winter Garden, FL

 

The City of Winter Garden presents Holiday Flix at the Garden. These holiday classic movies appeal to all ages and conjure past holiday memories -- and help to create new ones. See these festive flix in the timeless ambiance of the Garden Theatre while visiting the Holiday Wonderland in historic downtown Winter Garden.

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(Reservation/Ticket Required)

Dec 20 & 21
Garden Theatre

Winter Garden, FL 34787

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The Winter Garden Heritage Foundation is thrilled to partner with Opera Orlando to present two powerful performances of "All Is Calm: The Christmas Truce of 1914" at the historic Garden Theatre on Plant Street

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(Reservation/Fee Required)

Dec 6

10AM

Kick off from S. Dillard St & E. Plant St.

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Bring a lawn chair or blanket to your favorite spot for this annual holiday event.

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Dec 14

7347 W Sand lake Road​

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Dec 13

SeaWorld Orlando

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Bring the family out for the best Holiday Fun Run in the area. Run or walk the festive 3 mile route through SeaWorld to the sound of holiday bells and finish in a Runner wonderland with holiday treats for all finishers!

Together with WFTV - 9 Family Connection, Track Shack supports Toys for Tots.

 

(Reservation/Ticket Required)