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Free live music at gazebo

POSTED BY
Teresa

The City of Winter Garden provides free music every Friday night year-round in downtown’s Centennial Plaza Gazebo.

Fridays on the Plaza is from 7 to 9 p.m., and it’s free to hang out and listen.

Date night ideas: image of downtown entrance with bike trails and brick lined streets in downtown Winter Garden

Welcome to Winter Garden. Image: @officaldowntownwintergarden

Here is the schedule for the rest of 2026:

July

  • July 3 – Big Ron Betts Trio (Blues) – RED, WHITE & BLUES on the Plaza to Celebrate America 250
  • July 10 – Nic Weatherly (Rock)
  • July 17 – Cam Gordon (Acoustic) 
  • July 24 – David Julia (Blues)
  • July 31 – Raul Lugo (Steel Drums)

August 

  • August 7 – Amanda & Steve (Acoustic)
  • August 14 – PhoeNyx (Pop)
  • August 21 – Mike Quick (One Man Band)
  • August 28 – Bobby France (Rock)

September 

  • September 4 – Rowdy Jameson Band (Country)
  • September 11 – Sunshine Bluegrass Girls (Bluegrass)
  • September 18 – Bryant and Halloway (Folk)
  • September 25 – Gentleman of Jazz (Jazz)

October 

  • October 2 – Tom Grimes (Blues)
  • October 9 – Larry Poulton Band (Top 40)
  • October 16 – Crenshaw (Folk)
  • October 23 – Francesca Tarantino (Acoustic)
  • October 30 – TBD

November 

  • November 6 – Sammy Valez (Rock)
  • November 13 – MalCan’tHearYou (Indie Rock)
  • November 20 – Dale New (Classic Rock)
  • November 27 – Lucky to Be (Accoustic)

December 

  • December 4 – LIGHT UP WINTER GARDEN
  • December 11 – Dickens Carolers (Holiday Music)
  • December 18 – Mistletones (Holiday Music)
  • December 25 – No Scheduled Entertainment in Observance of Holiday.  

Centennial Plaza is a hub for shopping and dining in downtown Winter Garden. It also includes a clock tower.

Centennial Plaza is at 101 W. Plant St., Winter Garden.

Parking is available at Winter Garden’s three-level parking garage (160 S. Boyd St.), a 117-space parking lot (37 N. Boyd St.), and the City Hall parking lot (300 W. Plant St.). Parking is free in all downtown locations.

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