Downtown Winter Garden News

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. […]

Winter Garden Fall Heritage & Music Festival

November 3, 2021

The City of Winter Garden is celebrating its founding 118 years ago with a free community-wide Winter Garden Fall Heritage & Music Festival on Saturday, November 6, 8:00 am to 10:00 pm. Hosted by the City of Winter Garden and the Winter Garden Heritage Foundation, the daylong event includes multiple stages of live music, family-fun […]

10-Day Halloween Experience in Downtown

October 11, 2021

Downtown Winter Garden has turned into a spooky setting to bring a 10-day Halloween Experience to residents and visitors. After all, why should Halloween fun only last one night! Complimentary “frightening” family-friendly festivities will include animated light shows, pop-up street performers, live music, an outdoor movie, a hay maze, fall-themed photo stations, decorations, light displays, […]

Celebrate Hispanic Heritage Month

September 13, 2021

Hispanic Heritage Month is observed annually from September 15 to October 15. It initially started with a one-week commemoration in 1968 to honor the independence days of several Latin countries, which turned into a month-long celebration by President Ronald Reagan in 1988. It is a time to appreciate and celebrate the colorful cultures, rich histories, […]

Celebrate National Dog Month

August 18, 2021

August is National Dog Month! Our furry family members deserve a special month of love as a thanks for all they do for us. Fortunately, Downtown Winter Garden has many ways to celebrate your pooch while enjoying the last dog days of summer! The historic downtown Winter Garden district is proud to be dog-friendly, encouraging […]

Celebrate National Farmers Market Week

July 30, 2021

It is no secret that we have one of the nation’s best farmers markets right here in our backyard. The Winter Garden Farmers Market has been named America’s Favorite Farmers Market several times, a national award presented by the American Farmland Trust, along with being named the best farmers market in Central Florida by many […]

Top 10 Kid-Friendly Things to Do this Summer in Downtown Winter Garden

July 21, 2021

Summer is in full swing in downtown Winter Garden. Just 20 minutes from Orlando, Downtown Winter Garden has become a summer bucket list destination for many locals looking to explore beyond their own neighborhoods. In addition to an award-winning Farmers Market and unique mom and pop shops, downtown Winter Garden is also kid-friendly for all […]

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