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

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

December 2017

  • December 15 – Key Harmony (Acapella/Christmas Music)
  • December 22 – Safia Hudson (Christmas Carols/Holiday Pop)
  • December 29 – Good Times Jazz Band (Christmas Carols/Seasonal tunes)

January 2018

  • January 5- Retro Ramblers (Oldies, Pop)
  • January 12- Layla Brisbois (Acoustic Hits)
  • January 19- Tree Frogs (Classic hits, 60’s & 70’s)
  • January 25- Good Times Jazz Band (Jazz)

February 2018

  • February 2- Grimes Alley (Blues, Country, Acoustic Unplugged)
  • February 9- Da Capo Jazz Trio (Jazz)
  • February 16- Scotty Long (Folk, Country, 60’s to today)
  • February 23- Good Times Jazz Band (Jazz)

March 2018

  • March 2- Amy Robbins (American Folk, Country)
  • March 9- Molly Holton (Acoustic Blues)
  • March 16- Backyard Band (Electric Fusion, Bluegrass)
  • March 23- Good Times Jazz Band (Jazz)
  • March 30- Porchdogs (Cajun, Zydeco)

April 2018

  • April 6- Bob & Patty Tatum (Pop, Acoustic)
  • April 13- Crenshaw (Folk)
  • April 20- Jade Frances (Pop, Acoustic)
  • April 27- Good Times Jazz Band (Jazz)