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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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 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 12

3PM - 5PM

101555 W Colonial Dr
Ocoee, FL

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Free Photos with Mr. & Mrs. Claus by professional photographer

• Hot Chocolate & Holiday Treat Bar

• Kids Corner: Crafts, & letters to Santa

• Special Offer: Receive a free travel-size Alastin Skincare Bag (valued at $52) with any $100 purchase or more during the event!
• Holiday Gift Card & Membership Specials available

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Learn More

Dec 13

7AM

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)

Dec 13

3PM - 7PM

Home State Brewing 
16016 New Independence Pkwy

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Ho-Ho Home for the Holidays Market

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 25 Vendors
Holiday Photo Ops
Letters to Santa
Hot coco from Filigree
Live music by Heather DeSanctis

Grab a beer, cross off your gift list, enjoy live music and get in the holiday spirit with us!

 

Learn More

Dec 14

10AM - 1PM

1320 Daniels Rd
Winter Garden, FL

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Bring the family for a magical holiday event and free photos with Santa!

Enjoy refreshments and activities for children.

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Learn More

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 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 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 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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Learn More

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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Learn More

Dec 9

5PM - 7PM

Element

12802 W Colonial Dr

Winter Garden

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 Jingle & Mingle at Element 
Bubbles , bites , and holiday shopping  all in one! Globally sourced home decor!

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Learn More

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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Learn More

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!

Learn More​

Dec 3 - 22

Times Vary

Betty J's Florist

403 S Dillard St

Winter Garden, FL

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Each day has its own special moment… something simple, meaningful, and made to be shared with the people you love. 

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Learn More

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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Learn More

Dec 13

1PM - 7AM

Downtown Ocoee​​

Jolly Jamboree Dog Parade at 1 PM, then stay for the Jolly Jamboree until 7PM with games, an ICE SLIDE, music, rides, performances & more.

 

Learn More

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 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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Learn More

Dec 18

6PM - 8PM

Wheel Works

Downtown Winter Garden

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Join us for an after hours Holiday gathering. We are staying open late and encourage you to join your Wheel Works friends for seasonal festivities, food, drinks, prizes and cheer!

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Learn More

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 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.

Watch Video

Learn More

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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Watch Video

Learn More

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.

Learn More

Dec 9

6:30PM
Two Bridges Pub

16112 Marsh Rd.,

Winter Garden, FL

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EAT DRINK AND BE MURDERED- at the Finch Family annual ugly sweater party, one family member does NOT make it to Christmas Morning.

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(Reservation/Ticket Required

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)

Dec 5 - Jan 4

all day

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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Learn More

Dec 12

12PM - 5PM
Shannon Till State Farm

1620 Daniels Rd Suite 110
Winter Garden

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We invite neighbors, friends, and customers to partake in the holiday spirit with a Hot Cocoa Bar, scrumptious holiday treats, and lively karaoke.

 

Please bring a new, unwrapped toy to brighten the day of a child in need to be donated to Matthews Hope Orange County. Let’s come together to spread joy and cheer this holiday season.

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Learn More

Dec 13

8:30AM

Howey-in-the-Hills

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Let's kick off the holiday season with our friends in the town of Howey-in-the-Hills as we run or walk the AdventHealth Reindeer Dash 5K presented by Live Trends on beautiful Lakeshore Blvd. Onsite sponsor by Dash Sports

 

(Reservation/Ticket Required)

Dec 13

1PM

Downtown Ocoee
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Jolly Jamboree Dog Parade at 1 PM, then stay for the Jolly Jamboree until 7PM with games, an ICE SLIDE, music, rides, performances & more.

 

Learn More

Dec 14

7347 W Sand lake Road​

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Learn More

Dec 17

5:30PM

14111 Shoreside Way
Winter Garden

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CHANUKAH CELEBRATION
Donuts, Menorah Lighting, Fun for the whole Family!

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Learn More

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

Dec 31

6PM & 10PM

The Backyard

2214 West Road
Ocoee

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Want to celebrate NYE but be home before midnight? Then the NYE celebration at The Backyard is the place for you! Break out those PJ's (fancy or footie's...you do you!). However, this party will be anything but sleepy!

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(Reservation/Fee Required)

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.

Learn More

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!

Learn More

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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Learn More