Downtown Winter Garden News

Check here for the latest news, happenings, and announcements. There is always something new and exciting in Downtown Winter Garden!

Arts in April Events in Downtown Winter Garden

Celebrate Arts in April with a variety of community events for all ages to explore and create art in conjunction with World Art Day. From kids art sessions at the Winter Garden Farmers Market and Best of Show art exhibitions, to an Urban Sketchers competition, an Arts in April Light Show, and much more, there […]

Shop, Dine, & Stroll with Live Music in Historic Downtown

Spend the day visiting your favorite downtown shops and restaurants and discover some new ones at the daylong SHOP, DINE & STROLL event in scenic historic downtown Winter Garden on Saturday, March 25. The streets are abloom with spring flowers, providing a colorful backdrop for a stroll through the small town charm. In addition, live […]

Winter Garden Heritage & Music Festival Celebrates City’s 120 Anniversary

Established in 1903, the City of Winter Garden celebrates its 120th Anniversary with a Heritage & Music Festival on Saturday, February 11, from 11 a.m. to 10 p.m. The FREE, daylong event includes multiple stages of live music, kids’ entertainment, heritage activities, and much more. The downtown area, with its picturesque streets and historic buildings, […]

Downtown is for Making Merry Memories

There is something magical in the air in Downtown Winter Garden. You can just sense it as the sights and sounds of the season create a festive ambiance that feels straight out of a Norman Rockwell painting. Historic downtown is transformed into a charming winter wonderland with a host of free holiday events making it […]

Celebrate Small Business Saturday at Downtown Sidewalk Sale

The past two and half years have been filled with obstacles for our beloved small businesses. There is no better time to show up and support the small businesses that make up our incredible and eclectic downtown district. Small Business Saturday, the annual holiday when you can join in on all the fun and festivities, […]

Halloween is Scary Good in Winter Garden

Halloween is too fun to be celebrated on only one night. That is why the City of Winter Garden turns its downtown into a spooky, fun-filled Halloween Experience for 11 days! Skeletons perched on street signs, mammoth spiders crawling, bats hanging from trees; it is an amusing outdoor haunted house with a family-friendly twist. In […]

Ways to Celebrate National Hispanic Heritage Month

National Hispanic Heritage Month (September 15 – October 15) is a way to promote the history, culture, and contributions of Hispanic-Americans — specifically, those whose ancestors came from Spain, Mexico, the Caribbean, and Central and South America. Communities nationwide mark the achievements of Hispanic and Latino Americans with special events and educational activities, and Winter […]

Winter Garden Hosts Fourth of July Events

Winter Garden is hosting multiple, FREE Independence Day festivities over the long holiday weekend to celebrate America’s birthday. In addition, historic downtown is bursting with patriotic decorations accentuating its small town charm. From live music, a patriotic Farmers Market, a historical film screening at the Garden Theatre, to a down-home kids parade/pancake breakfast and a […]

Downtown is Blooming with Spring Events

The spring season is perfect for enjoying longer days, blooming flowers, and spending more time outdoors. Downtown Winter Garden is the perfect outing to enjoy the season whether you are strolling the brick-paved streets, swinging down by the Centennial Plaza fountain, splashing at the interactive fountain with your kids, or sitting at one of the many […]

Downtown becomes a Winter Wonderland

If you are looking for the best winter wonderland in Central Florida, visit Downtown Winter Garden in December. The historic downtown district is a premier destination for holiday fun throughout the month with a long list of “Tis the Season” events as well as festive surroundings to make merry memories. VISIT OUR WINTER WONDERLAND Historic […]


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