City of Winter Garden, FL

Home | Resident | Business | Visitor | City Hall | Public Safety

A charming little city with a juicy past

Special Events

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

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

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

June 2018

  • June 15- String Theory (Mo-town, Solo)
  • June 22- Good Times Jazz Band (Jazz)
  • June 29- Sandy Back Porch (Bluegrass)

July 2018

  • July 6- Jay McMullan (Americana w/harmonica, Jazz)
  • July 13- Keith Eaton (Soul)
  • July 20- Retro Ramblers (Oldies, Pop)
  • July 27- Good Times Jazz Band (Jazz)


  • August 3- Da Capo Jazz Trio (Jazz)
  • August 10- Ben Torres (Soft jazz, acoustic)
  • August 17- Holton Duo (Bluegrass, Country)
  • August 24- Good Times Jazz Band (Jazz)
  • August 31- Salted Vine (Pop, 60’s to today)


  • September  7- Amy Robbins Duo (American Folk, Country)
  • September  14- Backyard Band (Electric Fusion, Bluegrass)
  • September  21- Scotty Long (Folk, Country, 60’s to today)
  • September  28- Good Times Jazz Band (Jazz)


  • October 5- Mountain Brew (Irish, Bluegrass, Country)
  • October 12- Jade Frances (Pop, Acoustic)
  • October19- Crenshaw (Folk)
  • 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)