Downtown Winter Garden News

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

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

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 […]

Ways to Celebrate National Ice Cream Day

National Ice Cream Day is on Sunday, July 18, which is a perfect reason to indulge in this tasty treat! The holiday goes back to 1984 when President Reagan wanted to commemorate a treat enjoyed by over 90% of the population. The month of July was declared National Ice Cream Month with the holiday landing […]

Red, White and Blue Americana

Fourth of July in Downtown Winter Garden

Downtown Bursts with Fourth of July Festivities all weekend long! Fourth of July is almost here and if you are looking for ways to celebrate, Downtown Winter Garden has a host of festivities to enjoy! From live music and a patriotic Farmers Market to an old-fashioned kids parade/pancake breakfast and stunning fireworks spectacular, come out […]

The Exchange Exterior

Apricot Lane Boutique is First to Open at Plant Street Exchange

Exciting new shops and restaurants are coming to Downtown Winter Garden! The new Plant Street Exchange recently celebrated the opening of it first shop, Apricot Lane Boutique, earlier this month with more retail and restaurants coming soon. Located at 270 West Plant Street between city hall and the Downtown Interactive Fountain, Plant Street Exchange stands […]


The Ultimate Guide to Father’s Day

Look no further than Downtown Winter Garden for a fun Father’s Day celebration! Take a stroll or bike ride together; indulge dad with his favorite foods, coffee, and craft brew; go shopping to select a gift of his choice (no ties this year), and just enjoy the scenic surroundings together. Here are some things to […]

Winter Garden Farmers Market

Winter Garden Farmers Market 13th Birthday

The award-winning Winter Garden Farmers Market is turning 13 and you are invited to help us celebrate! Join us on Saturday, June 5th, for food demonstrations, live music, life-sized kids’ games, summer treats, and more! A number of fun activities are planned for the birthday celebration. Life size games such as Connect 4, Jenga, as […]

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

Updated 4/29/2022 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 […]


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