Downtown Winter Garden News

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

It is No Trick, Winter Garden Celebrates Halloween for 12 Days

It is no “trick” that Halloween is celebrated for 12 straight days in Winter Garden. Rather, it is a “treat” for the community to enjoy our downtown masked with spooky and fall-themed décor along with activities, and entertainment. Hosted by the City of Winter Garden, Halloween Experience 2023 (October 20-31) provides FREE family-friendly festivities in […]

Downtown Winter Garden to Host Summer Sidewalk Sale

The shops of historic downtown Winter Garden will host a Summer Sidewalk Sale on Saturday, August 26, 2023. Stroll the scenic streets to discover boutique bargains while enjoying the small town charm. The daylong sale is a great time to find deals on those one-of-a kind items that can only be found at downtown’s specialty […]

Winter Garden Hosts Nostalgic Fourth of July Events

Winter Garden is celebrating America’s birthday in a big way with several free community events. In addition to the Red, White & Blue Americana festivities, historic downtown is adorned in patriotic colors making it a nostalgic backdrop to stroll, dine, shop, take photos, and kick back with family and friends. The small town charm mixed […]

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 […]


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