City of Winter Garden, FL

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A charming little city with a juicy past

Special Events

Music Fest

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!

West Orange Health and Harvest Festival

Event Date: Saturday, October 29, 2016
Event Time: 9:00am to 2:00pm
Location: Downtown Winter Garden

Join local restaurants and their chefs in celebrating the bounty of local farms at the West Orange Health & Harvest Dinner. Dine on five courses featuring seasonal, local fare; paired with craft beer from Crooked Can Brewing, expertly-selected wines, and locally roasted coffee from Axum Coffee Company. For more information, click here.


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.

Winter Garden Craft Affair

Event Date:        Saturday, November 12
Event Time:        10 am - 2 pm
Event Location: 310 North Dillard Street

Arts & crafts lovers will enjoy shopping for unique and one of a kind items made exclusively by our 50+ creative friends.  Although our vendors are 50 or older, every one of all ages is invited to shop the fair for unique hand-crafted items.  Interested vendors please fill out and return the vendor application to

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!


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 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 Date: Saturday, December 3
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.


De-Light-Ful Decorations

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.

Ongoing Events:

Farmer’s Market

Event Date: Saturdays 9am - 2pm
Location: City Pavilion, Tremaine Street

Saturdays • 9:00am – 2:00pm
City Pavilion, Tremaine Street