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

7th Annual Winter Garden Blues & BBQ

FREE Admission • BBQ, Beer and Wine available for purchase

Event Date: Saturday, February 10th, 2018
Event Time: 4 - 10 pm
Event Location: Downtown Pavilion, 104 Lakeview Avenue

This festival pairs the hottest Blues and Roots musicians with award winning local BBQ connoisseurs, for an afternoon celebration of true Southern Soul. An exciting annual event that is not to be missed! 

4pm - Ari & The Alibis

6pm - Doug Deming & The Jewel Tones

8pm - Albert Castiglia 



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)