Downtown Winter Garden News

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

March 2, 2023

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

January 26, 2023

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

November 29, 2022

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

November 1, 2022

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

October 5, 2022

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

August 31, 2022

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

June 7, 2022

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

March 15, 2022

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

November 30, 2021

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 […]

Small Business Saturday

November 8, 2021

Small Business Saturday is an annual national holiday observed on the Saturday after Thanksgiving that focuses on the importance of supporting the small businesses in our respective communities. This year, the holiday is on November 27, and what better way to celebrate than to head to historic downtown Winter Garden for its annual sidewalk sale. […]

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