Sing Out Loud
Sing Out Loud is the annual, epic celebration of live entertainment in the Nation’s Oldest City.For one month every fall, the nation's oldest city turns up the volume. Music drifts through oak-shaded courtyards, historic streets, neighborhood breweries, intimate wine bars, record shops, and iconic outdoor venues. Residents and visitors wander from performance to performance, discovering new artists, reconnecting with old favorites, and experiencing the city through its soundtrack. This is Sing Out Loud—and in September 2026, it celebrates ten years of transforming St. Augustine into one of Florida's most authentic live music destinations.
The St. George Inn is one of the best properties downtown, and we are steps away from the free Local Artist Showcases. Across four weekends, more than 100 local and regional performers will fill 17 venues throughout the city with an extraordinary variety of music. Weekend One: September 4–6 Weekend Two: September 11–13 Weekend Three: September 18–20 Weekend Four: September 25-27 From indie rock and Americana to jazz, blues, bluegrass, country, folk, soul, and acoustic performances, nearly every musical style finds a home during the festival. .
Out. George Inn and our wine bar Bin 39 are s official Sing Out Loud showcase venue. We feature daily live music throughout the Sing Out Loud celebratory month of September The St. George Inn wine bar, Bin 39, also features live entertainment from over 25 local musicians throughout the entire month of September.
Participating venues include Colonial Oak Music Park, Dog Rose Brewing, Hornski's Brewing Co., Prohibition Kitchen, Ragga Surf Café, Sarbez, Spinster Abbott's, Casa de Vino 57, Bin 39 Wine Bar, the Lincolnville Museum and Cultural Center, Tonevendor Records, and numerous other independently owned establishments that give St. Augustine its unmistakable personality.