From Sept. 5 to 28, beautiful St. Augustine, Florida will be the setting for the Annual Sing Out Loud Festival. Presented by PNC Bank, this beloved yearly event’s series of free concerts features more than 100 local singers, songwriters and musicians. The Live Wildly Showcase is a highlight, with 2025 performances from Father John Misty, Hozier, sombr, Vance Joy, Sarah Kinsley, David Kushner, The Teskey Brothers, Brenn! And Gigi Perez. Francis Field in the Historic Downtown area is the setting, with $10 from each and every ticket sale used to support and further land conservation efforts in St. Johns County.

Festival-goers can also look forward to Sing Out Loud’s St. Augustine Songwriters Festival from Sept. 26 to Sept. 28, to be held at a selection of local venues; and the St. Augustine Record Fair at the St. Augustine Amphitheatre on Sept. 28, hosted by Tonevendor Records. There’s also An Evening with Chuck Leavell on Wednesday, Sept. 17 at the Ponte Vedra Concert Hall. Known as “The Tree Man,” Leavell was once the principal touring keyboardist and musical director for the Rolling Stones. He’s played with Eric Clapton, Pink Floyd and John Mayer; is a former member of the renowned Allman Brothers Band; and was the founding member of the band Sea Level.

Part of the festival’s fun is listening to performances in a collection of unique performance venues. These include The Waterworks, built in 1898 as the city’s first water pumping station; the Colonial Oak Music Park on historic St. George Street; Ragga Surf Café on the San Sebastian River; and the graceful Markland House on Flagler College campus.

Among the participating local and regional musicians this year are Bad Dog Mama, Billy Buchanan & His Rock ‘N Soul Revue, The Dunehoppers and ZaZa Flamenca.

St. Augustine is located between Daytona Beach and Jacksonville. Be sure to check out the festival website, which includes a trip planner to help visitors locate lodging and flights, and become familiar with the host of available local activities.