Special EventsView City Contact information
City of Winter Garden
300 West Plant Street
Winter Garden, FL 34787
Friday, October 7 | 6 – 11 pm
Saturday, October 8 | 1 – 11 pm
Sunday, October 9 | 1 – 5 pm
Plant Street | Free!
Produced by the Winter Garden Heritage Foundation. Join fellow music lovers at the eleventh annual three-day festival featuring dozens of acts performing in a variety of musical styles. Have a favorite? From jazz to rock, from gospel to bluegrass…you’ll hear it all!
Musicians will showcase their talents on a variety of stages and venues located along Plant Street in the heart of Winter Garden’s National Historic District. Sample dishes from a host of restaurants and vendors, and browse and buy at our unique local shops and festival booths. There’s something for everyone at this annual celebration of musical heritage!
Event Date: Monday Oct 31 2016 - 6:00pm
Location: Downtown Winter Garden
Features entertainment, local vendors and family activities! Enjoy a safe night of haunted happenings along downtown Plant Street! For a vendor application form please click here.
Holiday Market on Shop Small Saturday
Come out on the Thanksgiving weekend Saturday, November 26 for the holiday kick-off event and shop for everyone on your list!
WINTER GARDEN’S ANNUAL SANTA RUN
Monday, December 12 NE Area (North of 50 & East of Dillard)
Tuesday, December 13 NW Area (North of 50 & West of Dillard)
Wednesday, December 14 SW Area (South of 50 & West of 535)
Thursday, December 15 SC Area (South of 50 & 535 Subdivision)
Friday, December 16 SE Area (South of 50 & East of Daniels)
Time: 5:45 – 9 pm
The Winter Garden Fire Rescue Department will be escorting Santa Claus on his annual visit to neighborhoods in Winter Garden! Santa, along with his firefighter, police and city helpers will be spreading holiday music, candy and good cheer as they make their way through the streets of the city. Each night, Santa visits a different area of the city.
Check www.WinterGarden-fl.gov in November for Santa’s route.
29th Annual Light Up Winter Garden
Event Date: Friday, December 2
Event Time: 6 – 9 pm
6:15 pm Street lighting ceremony * Free!
Event Location: Downtown Winter Garden - Plant Street
Sponsored by Duke Energy, the West Orange Ministerial Association and the City of Winter Garden
Join us in welcoming the season with this annual event. Live entertainment, vendors, shopping, children's activities and more. Please click here if you are interested in being a vendor at Light Up Winter Garden.
Winter Garden Christmas Parade
Event Time: 10 am * Free!
Event Location: South Dillard Street & Plant Street
Bring a lawn chair or blanket and head to your favorite spot for this annual event. A long-standing Winter Garden holiday tradition will delight spectators and bring in holiday cheer! Don't forget to look for the Big Guy himself at the end of the parade! All entries will receive an email notification upon approval. Last day to enter is Friday, November 18th. Pre-registration to be in the parade is required for this event. Register online by clicking here or click here for registration form.
Event Date: Tuesday, December 6 & Wednesday, December 7
Event Time: 5:30 pm Judging begins * Free!
Drag out the lights, hang up the garland, put up the glowing Santa and enter your home to win! Festive presentations of outdoor decorations could win up to $100! Judging for Winter Garden's annual De-Light-Ful Decorations contest will take place on Tuesday, December 6 for homes North of Highway 50 and Wednesday, December 7 for homes South of Highway 50. Judging begins at 5:30 pm. Delightful Decoration application please click here.
Event Date: Saturdays 9am - 2pm
Location: City Pavilion, Tremaine Street
Saturdays • 9:00am – 2:00pm
City Pavilion, Tremaine Street