Downtown Winter Garden is kicking off a magical holiday season with fun for all the family!

Get ready for a jam packed December featuring Light Up Winter Garden. Winter Garden Christmas Parade, Winter Garden Christmas Golf Cart Parade, Holiday Night Market, A Merry Winter Garden Light Show, Main Street Holiday Stroll, and more!

There truly is something magical about Downtown Winter Garden during the holiday season. At the center of it all is Centennial Plaza, where a large, fully decorated Christmas tree dazzles.

This is where families gather, taking pictures, lifting little ones to gaze wide-eyed at each colorful ornament, where on Friday nights you can enjoy a free concert of holiday favorites.

The local shops and restaurants feel even more charming this time of year, with windows dressed in holiday cheer. Whether you are picking out last-minute gifts, discovering a new favorite shop, or just browsing, you are surrounded by the gentle yet excited hum of the community, all enjoying the ambiance and vibrancy.

A selection of holiday events hosted by the City of Winter Garden kick off the holiday season this weekend, bringing energy to the streets of downtown, attracting neighbors and visitors from near and far.

The holiday festivities begin on Friday Dec. 5 with the annual Light Up Winter Garden. On Saturday Dec. 6, you can enjoy the Winter Garden Christmas Parade at 10 am, then from 4 pm - 8 pm its the Holiday Night Market, enough holiday fun? No way, check out the Winter Garden Christmas Golf Cart Parade at 6 pm.

Check out our 2025 Guide to all magical fun this Holiday Season in Orlando. From the theme parks, to the attractions, shopping malls and resorts, you'll be dazzled with holiday options throughout Central Florida.

Beyond this weekend, A Merry Winter Garden Light Show take place on various nights throughout December. Plus the Main Street Holiday Stroll, an immersive holiday experience is happening from December 5, 2025 - January 4, 2026!

The holiday cheer continues with $5 holiday movies at Garden Theatre on Plant, including “White Christmas,” “A Christmas Story,” “National Lampoon’s Christmas Vacation,” among others.

For more details on Downtown Winter Garden, check out https://downtownwg.com

Check out the latest Christmas and Holiday News from throughout Central Florida. From the theme parks, to the attractions, shopping malls and resort hotels, you will be dazzled with holiday cheer, including the most spectacular events at the theme parks and attractions, glittering community events and parades, plus, magical parties, eats and treats, and so much more!

Before attending any of the events listed on Gotta Go Orlando, you should contact the organizer or venue to confirm that the event is taking place as information, changes, and cancellations can occur.

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