Sing Out Loud Festival 2025: Music Takes Over St. Augustine
Written by Emily (Mily) Ward | Sept 17, 2025
Sing Out Loud is the annual, epic celebration of live entertainment in St. Augustine, FL. Featuring a diverse mix of over 200 national, regional, and local artists, the festival spans multiple weekends each September, with both free and ticketed events across dozens of venues. Its marquee event, the Live Wildly Showcase, will light up historic downtown St. Augustine on Saturday, September 20, and Sunday, September 21.
When most people think of Florida festivals, the mind jumps straight to neon-lit stages and bass drops — EDM dominates the state’s live music landscape, from Ultra in Miami to Okeechobee and countless smaller raves sprinkled across the calendar. But Sing Out Loud Festival is a refreshing break from the strobes and drops. Instead of endless DJs, this one puts guitars, lyricism, and storytelling front and center.
This year’s lineup is stacked with artists across genres and generations, but a few names stand out for bringing fresh energy and emotional punch to the festival:
Sombr
Sombr’s dreamy yet haunting soundscapes have made them one of Florida’s most exciting rising acts. Their mix of intimate lyricism and atmospheric production feels tailor-made for late-night sets where emotions run deep.
2. Sarah Kinsley
Sarah Kinsley is redefining indie-pop with lush arrangements and cinematic flair. Known for her breakout track “The King”, she weaves classical influences into modern pop in a way that feels timeless and forward-thinking all at once.
3. Beabadoobee
With her blend of ‘90s-inspired alt-rock and bedroom-pop vulnerability, Beabadoobee has become a generational voice. Expect singalong anthems and cathartic guitar-driven moments that will echo through downtown St. Augustine.
4. Hozier
A festival headliner who needs no introduction, Hozier brings his soulful voice and politically charged ballads to the Live Wildly Showcase. From “Take Me to Church” to his latest releases, his set is sure to be one of the most anticipated moments of the weekend.
5. Gigi Perez
Gigi Perez is one of the most compelling new voices in alt-pop, blending raw emotion with sharp songwriting. Her music captures the turbulence of love, loss, and self-discovery with a punch that feels both intimate and universal.
Sing Out Loud isn’t just about the headliners — it’s about discovery. Across bars, theaters, and open-air stages, fans will stumble upon their next favorite band while soaking in the city’s historic charm. With its mix of community spirit and world-class talent, the festival continues to prove why St. Augustine has become one of Florida’s most vibrant cultural hubs.