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

15th Annual All American Kids Parade & Breakfast

Kids Eat Free!

Event Date: Wednesday, July 4th, 2018
Event Time: Breakfast will be served from 8 - 10 am * Parade begins at 10 am * Line-up starts at 9:45 am at the Masonic Lodge
Event Location: Winter Garden Masonic Lodge, 230 W. Bay Street

Sponsored by Winter Garden Masonic Lodge, Winter Garden Heritage Foundation and Winter Garden Downtown Merchants

For more information call the Heritage Foundation at 407-656-3244

Party in the Park

Event Date: Wednesday, July 4th, 2018
Event Time: 6 pm
Event Location: Newton Park, 29 West Garden Avenue

Bring a chair, blanket or have a seat in the grass for this annual Winter Garden tradition! Keep your eyes on the sky for one of the best firework displays in West Orange County. Live music, family activities, food and more keep the evening fun for all ages! Festivities begin at 6 pm. Fireworks show at 9:15 pm. Parking is available at Health Central Park and Dillard Street Elementary. If you are interested in becoming a vendor please click here.

2018 Red White and Blues on the Plaza

Event Date: Saturday, July 7th, 2018
Event Time: 7pm - 9pm
Event Location: Centennial Plaza

Come Downtown and spend some time on the swings or bring a chair and listen to the blues performed by Mud Rooster.

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)