City of Winter Garden, FL

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A charming little city with a juicy past

Special Events

City of Winter Garden
300 West Plant Street
Winter Garden, FL 34787

31st Annual Light Up Winter Garden

Free! Sponsored by Duke Energy, the West Orange Ministerial Association and the City of Winter Garden.

Event Date: Friday, November 30th, 2018
Event Time: 6 – 9 pm; Ceremony starts at 6 pm * Street lighting at 6:15 pm
Event Location: Downtown Winter Garden - Plant Street

It's that magical time of year again! Join us as we welcome the season with live entertainment, vendors, shopping, children's activities and more. Sponsored by Duke Energy, the West Orange Ministerial Association and the City of Winter Garden. If you are interested in being a vendor for this event please click here


Winter Garden Christmas Parade

Event Date: Saturday, December 1st, 2018
Event Time: 10 am
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 16th. Please click here to register for the parade. 

De-Light-Ful Decorations


Event Time: Tuesday, December 18 & Wednesday, December 19 * Judging begins at 5:30 pm

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 begins at 5:30 pm. All interested participants should complete the application and submit to the Parks and Recreation Department at by Friday, December 14. 


Ongoing Events:

Winter Garden Farmers Market

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

The Winter Garden Farmers Market is your hometown market open every Saturday from 9:00am to 2pm in beautiful Historic Winter Garden. 

The Market has quickly grown into a community staple and offers a large selection of vendors from locally grown produce and baked goods, to homemade soaps and fresh flowers, and even live entertainment each week! 

Bring the whole family (even your four-legged friends) and experience what makes the Winter Garden Farmers Market so special. 

Enjoy LIVE MUSIC every Saturday from 10:00am to 2:00pm

Cruz N Car Show

Event Time: 4pm - 8pm
Event Location: Downtown Winter Garden






The Cruz N Car show is held quarterly in Downtown Winter Garden on the third Saturday in January, April, June, and September from 4 to 8 pm.

  • January 20, 2018
  • April 21, 2018
  • June 16, 2018
  • September 15, 2018

Click here for Cruzin' details.

Friday’s on the Plaza

Event Time: 7 - 9 pm
Event Location: Downtown Winter Garden

Come enjoy live music every Friday night on the Plaza


  • October 5- Mountain Brew (Irish, Bluegrass, Country)
  • October 12- Jade Frances (Pop, Acoustic)
  • October19- Bird Dog Bobby Band (Blues)
  • October 26- Good Times Jazz Band (Jazz)


  • November 2- Grass Fed (Bluegrass)
  • November 9- Porchdogs (Cajun, Zydeco)
  • November 16- Grimes Alley (Blues, Country, Acoustic Unplugged)
  • November 23- Good Times Jazz Band (Jazz)


  • December 7- Nicole Equerme w/Sam Trawick (Holiday Music)
  • December 14- Key Harmony (Acapella Holiday Music)
  • December 21- Safia Hudson Trio (Holiday Music)
  • December 28- Paint it Black Quartet (Holiday Music)