Orlando on the Cheap

Deals, discounts and free and cheap things to do in and around Orlando

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 2026:

January

  • January 2: Allie Sawicki (Top 40)
  • January 9: Big Ron Betts (Blues)
  • January 16: Nic Weatherly (Rock)
  • January 23: Francesca Tarantino (Acoustic)
  • January 30: Amanda & Steve (Acoustic)

February

  • February 6: Gentleman of Jazz (Jazz)
  • February 13: Evan Taylor Jones (Soul Rock)
  • February 20: PhoeNyx (Pop)
  • February 27: Martin and Kelly (Country)

March

  • March 6: Concrete and Country (Country)
  • March 13: Crenshaw (Acoustic)
  • March 20: Theo Moon Music (Acoustic)
  • March 27: Tom Grimes (Blues)

April

  • April 3: Lucky to Be (Acoustic)
  • April 10: Dale New (Sonic Architect)
  • April 17: Beautiful Music Jazz Trio (Jazz)
  • April 24: Sound Traveler Band (Acoustic)

May

  • May 1: Sammy Valez (Rock)
  • May 8: The Danny Alan Trio (Top 40)
  • May 15: Salted Vine Band (Classic Rock)
  • May 22: Molly M (Pop / Top 40)
  • May 29: Gentleman of Jazz (Jazz)

June

  • June 5: Scott Davidson (Rock)
  • June 12: Lynne Gibson (Classic Rock)
  • June 19: Theo Moon Music (Acoustic)
  • June 26: Francesca Tarantino (Acoustic)

July

  • July 3: Big Ron Betts Trio (Blues)

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.

MORE FREE & CHEAP THINGS TO DO IN ORLANDO

For more Orlando discounts: 

Stay connected with Orlando on the Cheap (for FREE)!

 

Reader Interactions

Leave a Reply

Your email address will not be published. Required fields are marked *

MEMBER OF THE LIVING ON THE CHEAP NETWORK

Orlando on the Cheap is a member of Living on the Cheap, a network of websites published by frugalistas, journalists and consumer advocates. Find practical advice on saving money on groceries, travel and shopping, plus tips from our experts on how to live the good life for less at Living on the Cheap.
Living on the Cheap in the media