Sing Out Loud Turns 10: Free Music Fills 17 St. Augustine Venues Over Three September Weekends

St. Augustine's Sing Out Loud Festival turns 10 this month, and the celebration is spread across 17 venues downtown over three straight weekends in September. More than 160 acts will play for free between Sept. 4 and Sept. 20, covering indie rock, jazz, bluegrass, country, comedy and spoken word, all part of the festival's Local Artist Showcases.

For residents who plan their weekends around it, that means live music within walking distance of home for nine days spread across the month, no ticket required. The showcase weekends run Sept. 4-6, Sept. 11-13 and Sept. 18-20, with full lineups and showtimes posted at singoutloudfestival.com and on the festival's official app.

This is the first year the festival has split its programming this way. Since Sing Out Loud launched in 2016, its marquee Francis Field weekend has shared the calendar with the local showcases. Not anymore. That larger event is moving to May 2027, giving the September dates over entirely to the hundreds of Northeast Florida musicians who normally share the bill with touring headliners.

Organizers say the festival has now featured more than 1,700 musicians and drawn over 360,000 attendees since it began a decade ago. The local showcases have been part of that story from the start, built around the idea that St. Augustine's independent bars and listening rooms are as much a draw as any single headliner.

Two surprise shows worth planning around

Sing Out Loud has a history of dropping surprise sets into the schedule, and this year's additions, booked with the St. Johns Cultural Council, are bigger than usual.

• Friday, Sept. 11: Grammy-winning singer and multi-instrumentalist Aoife O'Donovan performs with the St. Augustine Bluegrass Unit and Eowyn Sage at Spinster Abbott's. Free and open to the public.
• Sunday, Sept. 13: The Sam Grisman Project performs alongside a screening of the documentary "Summer Tour" at Ponte Vedra Concert Hall.

A flavor to match

Mayday Handcrafted Ice Cream is marking the anniversary with a limited-edition flavor called Spoonbill Guava Cheesecake, a guava-lime ice cream studded with crumbles of Mayday's own cookies. It's named for the pink-and-white roseate spoonbill found around the region and will be sold only at Mayday's St. Johns County locations through September.

Beyond the September showcases, the St. Augustine Songwriters Festival follows later in the month, and a record fair is planned at the St. Augustine Amphitheatre. Organizers haven't released ticket details for the May 2027 Francis Field weekend yet, but the local showcases running this month are free to all, with schedules updated in real time on the festival's app as sets get added.

Want to talk about this year's lineup or trade notes on which venue to hit first? Head over to our Community Forum to join the conversation. For more on what's happening around town this month, check out our events coverage and lifestyle and entertainment stories, or visit the St. Augustine Community Website homepage for the latest local news.