St. Augustine Songwriters Festival

The 8th Annual St. Augustine Songwriters Festival fills St. Augustine's historic district with music from Friday, September 26, through Sunday, September 28, 2025. 

The three-day festival presents Nashville singer/songwriters, including some with local roots, for free concerts in four locations. During each set, two to four songwriters take turns performing, perhaps sharing how a song came to be, and often bantering with the other songwriters. 

The festival features songwriters ranging from legendary artists to current hit makers and budding stars. The 2025 lineup has not been released. The 2024 lineup included Gretchen Peters, Rivers Rutherford, and St. Augustine's Davis Loose. Brett James, who wrote "Jesus, Take the Wheel;" Liz Rose, who collaborates with Taylor Swift; and Matt Dragstrem who has several #1 hits with artists that include Blake Shelton, Luke Bryan, and Florida Georgia Line.

The free performances will take place at the following venues:

• Colonial Oak Music Park (27 St. George Street)

• Prohibition Kitchen (119 St. George Street)

• St. Augustine Distillery (112 Riberia Street)

• Tradewinds Lounge (124 Charlotte Street)

Admission: Free

When: Afternoons and evenings from Friday, September 26, through Sunday, September 28, 2025

Where: One of the above four venues, all in the historic district. 

Sponsors: The St. Augustine Songwriters Festival is partially supported by Bozard Ford, the Sing Out Loud Festival, VisitStAugustine.com, Hampton Inns, St. George Inn, Old Town Trolley Tours, and the Colonial Oak and Pirate & Treasure Museum.