Special Events
-
Fridays on the Plaza
Come enjoy live music every Friday night on the Plaza in Winter Garden.
-
Winter Garden Farmers Market
Held every Saturday, the market is a community staple with 100+ vendors offering a large selection items from locally grown produce and baked goods, to homemade soaps and fresh flowers, etc. and even live music.
-
Craft Affair 2023 - November 11
Arts & crafts lovers will enjoy shopping for one-of-a-kind handmade items at the annual Craft Affair, hosted by the City of Winter Garden Parks & Recreation. FREE ADMISSION.
-
Small Business Saturday 2023 – November 25
Kickoff holiday shopping while loving local at the Small Business Saturday celebration in festive-decorated historic downtown with outdoor LIVE MUSIC! Citywide, Shop Small to make a Big Impact!
-
Tis the Season Event Schedule 2023
Downtown Winter Garden transforms into a winter wonderland for 38 days of Tis the Season (Dec. 1- Jan. 7). Click to learn more about all the free downtown holiday happenings and the seasonal resident programs to make merry memories!
-
Light Up Winter Garden 2023 - December 1
Join us to welcome the holiday season at our 37th annual Light Up Winter Garden on Friday, December 1, 6-9 pm. The free event includes holiday entertainment, children's activities, and lots of holiday fun!
-
Winter Garden Christmas Parade 2023 – December 2
Bring a lawn chair or blanket and head to your favorite spot for this annual holiday event. A long-standing Winter Garden holiday tradition will delight spectators and bring in holiday cheer! Do not forget to look for the Big Guy himself at the end of the parade!
-
Holiday Market at Downtown 2023 – December 2
Wander freely through the pedestrian-only streets of historic downtown aligned with vendor booths of holiday décor, crafts, jewelry, apparel and accessories, sweet treats (including Gingerbread), variety of gift items, and more including FREE CHILDREN’S HOLIDAY ENTERTAINMENT!
-
WG Christmas Golf Cart Parade 2023 – December 2
The 11th Annual Christmas Golf Cart Parade is an amazing sight of festive elaborately decorated golf carts making their way through historic downtown to spread holiday cheer. The parade loops around West Plant, entering east bound from Park Avenue and looping westbound on Woodland Street. Spectators should stake their favorite viewing spot along West Plant Street and bring a chair for comfort.
-
De-light-ful Decorations Contest 2023
Drag out the lights, hang the garland, put up your outdoor holiday yard decorations, and enter your home to win the City of Winter Garden 2023 De-light-ful Decorations Contest!
-
Winter Garden Fire Rescue Annual Santa Run 2023
The Winter Garden Fire Rescue annual “Santa Run” brings Santa and his sleigh through City of Winter Garden neighborhoods. The moving parade takes place between 5:45-9:00 pm each night as Santa, along with his elves (firefighter, police, and city helpers), spread holiday cheer, music, and treats along the way.