St. Augustine’s 4th annual Sing Out Loud Festival is kicking off this weekend at venues throughout the historic district and organizers are expecting the biggest crowds ever! Concerts are planned for each weekend from Friday, September 6 through Sunday, September 29.

The event will feature an impressively orchestrated 334 bands including headliner Kacey Musgraves as well as local poets and comedians. In total, fans will be treated to more than 500 artists.

No matter your musical tastes, the festival has shows for you including indie rock, Americana, blues, hip-hop and R&B, bluegrass, punk rock, jazz and comedy.

Almost all of the festival’s shows are free to attend—a rarity when it comes to great concerts—and require no tickets. The only show to charge admission is the (sold out) finale with Grammy Award-winning country music star Kacey Musgraves on September 21.

Here are just some of the featured performances each weekend. Except for the first show below, all featured shows will be at The Backyard at The St. Augustine Amphitheatre. See a full schedule at

  • Friday, Sept. 6 (starting at 6 p.m.)Headliner: Dave Hause & The Mermaid, Guests: Christina Wagner, Raye Zaragoza, The Attack (Venue: Colonial Oak Music Park)
  • Saturday, Sept. 7 (starting at 7:45 p.m.) – Headliner: Kurt Vile and the Violators, Guest: Reels
  • Sunday, Sept. 8 (starting at 6 p.m.) – Headliner: Jenny Lewis, Guests: The Watson Twins, Lucie Silvas
  • Friday, Sept. 13 (starting at 5:30 p.m.) – Headliner: Propagandhi, Guests:The Coathangers, Debt Neglector, GILT
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Each Thursday between Memorial Day and Labor Day, St. Augustine turns from the Oldest City into Music City USA! That’s thanks to Concerts in the Plaza, which is kicking off its 29thseason tonight.

Each Thursday evening, a different local and regional musical act performs in the gazebo of the Plaza de la Constitución in historic St. Augustine. The free concerts last from 7 to 9 p.m. Spectators are welcome to bring chairs, blankets and coolers (no alcohol please) to set up on the lawn and enjoy the show.

Here is this season’s lineup and the style of music for each:

May 30 – The Driftwoods (bluegrass)
June 6 – The Raisin Cake Orchestra (New Orleans jazz)
June 13 – The Grapes of Roth (classic rock)
June 20 – The Mike Hart Band (blues/rock/jazz)
June 27 – Timberwood (acoustic folk/rock)

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