Downtown Winter Garden News

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


Downtown Displays Patriotic Charm

In honor of Memorial Day, Downtown Winter Garden will be decked out in patriotic colors and decorations accentuating its small-town charm. Red, White & Blue Americana in Downtown Winter Garden will run from Memorial Day through Independence Day. Our patriotic spirit and decorations will make Downtown WG an ideal holiday setting for patronizing local shops […]

Cyclists riding through Downtown Winter Garden on the West Orange Trail

Winter Garden Celebrates National Bike Month

May is National Bike Month, a celebration of biking as recreation, transportation, and a healthy activity for our well-being and everyday lives. Promoted by the League of American Bicyclists, National Bike Month is a chance to showcase the many benefits of bicycling — and encourage more folks to give biking a try. With a 22-mile, […]

Cyclists Riding by the Train Caboose on the West Orange Trail

Historic Preservation Month

The month of May is National Historic Preservation Month, where we celebrate historic places and the preservation of those historic places to encourage a brighter future. Today we get to enjoy the beautiful and charming city of Winter Garden with all its great shops, restaurants, and things to do. But part of the reason that […]

Outdoor Dining Month in Winter Garden

The City of Winter Garden proclaims May as Outdoor Dining Month! It’s the perfect time to enjoy spring weather and a side of sunshine at the many fresh air dining options throughout Winter Garden. Dine amongst historic charm and scenic flowers and greenery along the umbrella lined streets of Downtown Winter Garden. Visit the many […]

Grandfather and granddaughter recycling

6 Ways to Celebrate Earth Day

Every April 22nd we celebrate Earth Day as a way to honor and appreciate our precious planet. Earth Day is also an important reminder that our community can play a role in protecting our planet every day. Here are 6 ways you can help to care for our planet and honor Earth Day. 1. Ride […]

SOBO at Night Outside

Why Local Arts Matter [Behind the Scenes]

The City of Winter Garden has been driving the community to support local businesses and keep our town afloat through the Love Local Initiative. Love Local is all about supporting the small businesses that make Winter Garden such a unique and special city. The month of April is dedicated to supporting and showcasing the local […]

Arts in April: Community Celebration

On Saturday, April 17th, Downtown Winter Garden will be having a day-long community celebration for all ages to enjoy and explore art, while showing appreciation to the local arts. Themed “The World Outside,” all daytime activities are free and open to everyone! Make sure to come by and participate in the festivities. Keep reading to […]

Arts in April: Art Night VIP

On Saturday, April 17th, Downtown Winter Garden will be having an all-day-long community celebration to support the local arts. Once evening hits, the downtown streets will be lit up for everyone to enjoy and a ticketed Art Night VIP event will take place from 6 pm – 9 pm. The ticketed event will be a […]

Get Ready for Arts in April

The Winter Garden community places a very high importance on the Arts and the role it plays in bringing our community together. “The arts matter because they help us see the world from different perspectives. They give us empathy and help us understand people, places, periods of history, and issues with which we may otherwise […]

Why Winter Garden Ranks for Relocation Among Small Cities

Winter Garden Ranked No. 24 on a list of the Most Popular Small Cities To Relocate to in 2020. Winter Garden is one of the most sought out small cities to relocate to in the country, ranking 24th according to a study of those who relocated in 2020 conducted by MoveBuddha. The national relocation consulting […]

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