Sing Out Loud Music Festival: St. Augustine’s September Soundtrack

by Kevin Howard

St. Augustine is turning up the volume this month—Sing Out Loud Music Festival is back! From September 5 to September 28, our historic city becomes a vibrant, month-long destination for music lovers. Whether you’re a local or visiting, there’s no better time to celebrate the rhythm, the culture, and the community spirit that make St. Augustine unforgettable.

What’s in Store?

1. Local Artist Showcases

For the first three full weekends—September 5–7, 12–14, and 18–21—enjoy free performances across intimate venues like Colonial Oak Music Park, The Waterworks, Spinster Abbott’s, Dog Rose Brewing Co., and Ragga Surf Café. These showcases spotlight indie rock, bluegrass, hip-hop, country, spoken word, comedy, and more—over 100 musicians bringing local sound to life. For a full list of showcases, click here.

2. Live Wildly Showcase: A Music Spectacle

The centerpiece event! Held September 20–21 at Francis Field, this two-day concert series features national headliners:

September 20: Beabadoobee, Vance Joy, Father John Misty, Maren Morris, David Kushner, Sarah Kinsley
September 21: Hozier, The Teskey Brothers, Rilo Kiley, Gigi Perez, Sombr, Brenn!

It’s a ticketed event where $10 from each sale helps fund land conservation efforts in St. Johns County. Click here for more information and to purchase tickets.

3. Special Events & Programming

An Evening with Chuck Leavell (“The Tree Man” Experience) on September 17 at Ponte Vedra Concert Hall—a ticketed evening of music, film, and conversation, with a conservation fee included.
Music Business Panel on September 24 at Markland House (Flagler College)—free with RSVP, great for industry professionals or curious creators.
St. Augustine Songwriters Festival (September 26–28): Hear Nashville songwriters perform and share insights at Colonial Oak Music Park, Tradewinds Lounge, Prohibition Kitchen and other venues.
St. Augustine Record Fair on September 28 at the Amphitheatre—free and family-friendly, featuring vinyl, merch, screen printing, food trucks, and DJs.

Why It Matters — More Than Just Music

Community & Culture: This festival interweaves national artists with local talent, bringing together diverse sounds in venues that define the city's cultural heartbeat.
Economic & Environmental Impact: Ticket proceeds support conservation, while showcases across restaurants, bars, and public spaces drive downtown foot traffic and local business.
Variety of Experiences: Whether it’s an intimate acoustic set in a café, a major concert under the stars, or an industry panel—you’ll find something rich, meaningful, and memorable.

Tips for Visitors

Plan Early: The Live Wildly Showcase draws crowds—tickets and accommodations fill up fast.
Mix Paid & Free: Combine budget-friendly local showcases with one or two headline events for a balanced experience.
Explore the City: Encourage visits to historic landmarks, dining, art galleries, and scenic spots before or after performances.
Use Shuttle & Parking Info: Especially for the Live Wildly events, shuttle service (e.g., from Vilano Beach to Downtown) simplifies logistics.

Final Thoughts

Sing Out Loud isn’t just another music festival—it’s a celebration of St. Augustine’s soul. As the city aligns its historic charm with passionate performances and vibrant community moments, the festival invites all to partake in something authentic and electrifying.

If you’re a local homeowner, this is a perfect opportunity to host friends or family, blend local pride with cultural pride, and showcase just what makes living here so special. And if you're considering a move to St. Augustine, FL? Sing Out Loud is a compelling reason to explore St. Augustine’s lifestyle—and perhaps make it your forever home.