Downtown is Magical During the Holiday Season

November 20, 2025

There’s something magical about Downtown Winter Garden during the holiday season. As soon as you come upon Plant Street, the mood softens; the air is sweet, threaded with the scent of cinnamon, sugar, and spice from local bakeries; and the milder Florida temps drift softly through the large oak trees.

The lights that envelop the West Orange Trail lead you down the cozy strip of Plant Street, nestled between historic buildings and small businesses with decorated windows, calling you to step inside while wandering, not rushing.

At the center of it is Centennial Plaza, where a large, fully decorated Christmas tree dazzles. Around the perimeter, you’ll see families making memories, taking pictures, lifting little ones to gaze wide-eyed at each colorful ornament.  Sit and swing, or hang out by the gazebo, 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 bring energy to downtown streets, which are filled with neighbors and visitors. Everyone has their own holiday bucket list, like witnessing downtown becoming aglow with a flip a switch at Light Up Winter Garden, seeing their children’s eyes light up while watching the down home Winter Garden Christmas Parade, hoping to catch a glimpse of their favorite decorated golf cart at the annual Winter Garden Christmas Golf Cart Parade, gazing in awe at the festive light show projected on City Hall, or discovering a new treat at the Holiday Night Market.

Some come dressed in their best holiday outfits for a night at Garden Theatre on Plant for special Holiday performances like A Christmas Carol, or All is Calm: The Christmas Truce of 1914; while some come in their comfiest holiday pajamas to catch their favorite Holiday Flix like “White Christmas,” “A Christmas Story,” “National Lampoon’s Christmas Vacation,” among others.

The holiday feels last for the entire month of December, so even if your busy schedule doesn’t allow you to take part in the many festive downtown events, you can visit at any time, day or night (December 5 – January 4), to experience the magical transformation of downtown into a holiday wonderland, complete with an enchanting Main Street Holiday Stroll, and get to partake in the festive magic and joy of Downtown Winter Garden during the season.