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Tis the season! Explore these ways to celebrate in Winter Garden this year.

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Detox and Tox Pary

December 1st
15516 W Colonial Dr
Winter Garden FL 34787

Do you need a dose of healthy energy? All attendees will receive FREE B-12 injections!
Refresh for the holidays with Tox! $10/unit onsite or scheduled for a later date!
IV Hydration & Nutritional Therapy!!!
Exclusive deals on aesthetics and wellness services!
Stellar deals on studio membership enrollment!
Retail discounts and shopping bundles you don’t want to miss!
Raffles & Giveaways!
Refreshments and more!


A BIG Band Christmas

December 2nd
Following Light Up Winter Garden

Join us on the front steps of Historic Downtown First Baptist Church immediately following Light Up Winter Garden for “A Big Band Christmas” featuring Charles Billingsley and Dave Boyer along with the First Baptist Worship Band and Foundation Academy Steel Drums.

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Santa’s Lane

December 3rd
3 - 6pm
230 N Tubb St
Oakland FL

“Santa’s Lane” is returning bigger and jollier than ever with more sparkling lights and new activities including an alpine slide, snow flurries, food trucks, music and more!
Guests will have the opportunity to sit with Santa for a free photo opportunity and kids will go home with a special treat from the North Pole, while supplies last.


Christmas Spectacular

December 10th
6 - 9 pm
Gymnastics USA
13175 W Colonial Dr
Winter Garden FL


Hosted by: G.USA, We Are Winter Garden and Healthy West Orange!

Food Trucks, Santa Visit, WHOLE Family Open Gym, Winter Garden Vendors, Rock Climbing, DJ Music, Raffles & Prizes, Winter Garden Swag, Snow Fall, and CHRISTMAS!


Holiday Tour of Homes

December 17th
Oakland & Winter Garden

Come journey with us and experience the magic of the holidays benefiting Eight Waves. Step into four Oakland and Winter Garden’s estate homes while you experience a variety of savory and sweet tastes of the holidays. To quench your palate, beverages will be at your fingertips while sounds of the season ring nearby.

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A Blue Christmas Service

First United Methodist Church of Winter Garden
December 21st
125 N Lakeview Ave
Winter Garden, FL 34787

This is a special service of meditation, remembrance, prayer, and candles. A service for those who mourn or are hurting during the holidays. May the Lord comfort and strengthen you all.

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NYE 90’s Party at Home State Brewing!

December 31, 2022
16016 New Independence Pkwy
Unit 100
Winter Garden, FL 34787

Get jiggy with us this New Year’s Eve!🕺🪩
We all remember the 90’s with all of the classic TV shows, movies, and tunes.

For one night only we can relive that incredible decade and have hella fun!🖍️📺🛍️🧃🛹

Come FRESH, dressed in your 90s best and bring the crew!


Brosway Launch at Polka Dotz

December 1st
12 W Plant St
Winter Garden FL

Polka Dotz is celebrating their newest Brosway Italia jewelry line. It’s quickly expanding in the US and Polka Dotz are the first to have it in Central Florida.
Brosway Italia’s US expansion is being spearheaded by none other than Giovanni Feroce, former CEO of Alex and Ani who skyrocketed that brand into superstardom.
Expect giveaways every 30 minutes, good wine, charcuterie, laughs and lots of fun.


 Winter Garden Christmas Parade

December 3rd
10 AM - 12 PM

Bring a lawn chair or blanket and head to your favorite spot for this annual holiday event. A long-standing Winter Garden holiday tradition will delight spectators and bring in holiday cheer! Don't forget to look for the Big Guy himself at the end of the parade!

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Christmas Golf Cart Parade

December 3rd
6 pm
Downtown Winter Garden
Winter Garden FL

Sponsored by West Orange Junior Service League & The City of Winter Garden.
Parade Starts at 6:00 (Viewing Opportunity from W Plant Street in Downtown WG)
Golf Carts will be parked after Parade on W Plant Street for closer viewing.

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Jingle Jolly 5k

December 10th
5 pm
1054 Pawley Way
Oakland, FL 34787

Kick off the season with the the 13th annual 5K. Come run or walk this evening race and enjoy the festive holiday decorations through beautiful Oakland Park subdivision.

This event features a 5K, Kid's Fun Run, Meet & Greet with Santa and his elves, festive activities, food trucks, live DJ and more.

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Home State Brewing

December 17th
16016 New Independence Pkwy #100
Winter Garden, FL 34787

Bring the family out Saturday, December 17th from 1-5 for a day full of fun!

☃️ Kids crafts
🎨 Face Painter
🎄 Christmas family photo op

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Playa Pizza: Best New Year’s Ever!

December 31, 2022
8 - 2am
Playa Pizza
13211 Reams Rd
Unit 108
Windermere, FL 34786

Celebrate New Year's Eve at Playa Pizza! There'll be music by Pacific Rush, all the amazing Playa Pizza food you love, the greatest view of the Magic Kingdom fireworks, and our awesome selection of local craft beers!


Light Up Winter Garden

December 2nd
6-9 pm
City Hall, 300 W. Plant Street
Winter Garden, FL
(Lighting) and throughout Historic Downtown

Join us to welcome the holiday season at the 35th annual Light Up Winter Garden to kick off downtown's 38 days of Tis the Season. The lighting will take place at 6:15 pm at City Hall followed by various activities for all to enjoy.


Christmas Market on Plant Street

December 3rd

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 festive-adorned streets with holiday music filling the air. Perfect atmosphere for grabbing a hot chocolate to sip as you stroll!

Go from shop-to-shop to find the perfect gifts without having to worry about cars or traffic. Many will have outdoor tables and racks with specialty merchandise and special savings for convenient perusing and purchasing.


Holiday Boutique Stroll

December 8th

Holiday shopping at its finest with a stroll of the boutiques of Downtown Winter Garden to find unique presents while enjoying complimentary light refreshments, in-store raffles, outdoor/indoor specials and promotions, seasonal merchandise, and more! Look for the Balloons at the Participating Boutiques and make a purchase to enter the Grand Prize Raffle to win gift basket worth over $400!


Winter Garden Fire Rescue Annual Santa Run

December 12th - 17th 

Santa will be in the following areas from 5:45 − 9:00 pm on the following dates:


  • Monday, December 12 − North West Winter Garden

  • Tuesday, December 13 − North East Winter Garden

  • Wednesday, December 14 − South Winter Garden: CR 545 Corridor (West Side)

  • Thursday, December 15 − South Winter Garden: CR 545 Corridor (East Side)

  • Friday, December 16 − South Winter Garden: CR 535 / Daniel’s Road Corridor

  • Saturday, December 17 − South Winter Garden: Beulah / Windermere Road Corridor


Matthew’s Hope Community Christmas Carnival

December 17th
10:00 am - 2:00 pm
611 Business Park Blvd #101 Winter Garden Fl

The entire community is invited to enjoy the carnival festivities and get their child’s wish list!!! Our ultimate desire is to provide a dignified opportunity to those struggling in our community to have a Merry Christmas.

For more information, please contact:, or call 407.905.9500

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Christmas Eve at Hope

December 24, 2022
100 Windermere Rd
Winter Garden, FL 34787

This year we will be having two Christmas Eve services at 4PM and 5PM.

Doors will open at 3:30 and we will be having some Family Fun stuff happening outside between the services!

SNOW (Florida Style )
Possibly an appearance by Santa
Cookies and Cocoa
Photo Ops

Be sure to invite your friends and family! You don't want to miss it!

*Childcare available for children 3 years and younger

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