Recently ranked among the top ten most walkable cities in the United States. St. Augustine comes alive with sound this September. The lively Sing Out Loud Festival fills the month with unforgettable performances from local and national artists.
Classical concerts warm historic halls, while open-air stages pulse with rock, folk, indie, beats, and more. Between concerts, explore centuries-old landmarks and indulge in local dishes. Listen to each note as they weave together for a getaway you’ll remember after the final encore.
Sing Out Loud: St. Augustine’s September Soundtrack
Every September, the Sing Out Loud Festival turns St. Augustine into a citywide stage. More than 100 national, regional, and local artists perform in courtyards, theaters, and along the waterfront. The festival spans multiple weekends, offering a mix of free and ticketed events. Each performance adds to the energy, inviting visitors to experience music in fresh ways. The Live Wildly Showcase is set for September 20 and 21. Crowns the celebration with two nights of unforgettable concerts in downtown St. Augustine.
Who is Performing at Sing Out Loud 2025?
The Live Wildly Showcase brings an impressive lineup to downtown St. Augustine. Headliners include Hozier, Beabadoobee, and Vance Joy. The Teskey Brothers are also on the bill. Billy Buchanan & His Rock ’n Soul Revue and Cat Ridgeway & The Tourists will perform. Although every artist has been announced, we’re not listing them here. We’re saving some surprises for when you check the full schedule.
Tickets are sold exclusively through the Sing Out Loud Festival website or AXS. They can also be purchased at The St. Augustine Amphitheatre Box Office. Buying from other sources is at your own risk. Third-party tickets cannot be verified and may be invalid for entry.
After the Festival: Adventures and Flavors in St. Augustine
Adventurous spirits will find plenty to explore after the music fades. Climb the 219 steps of the St. Augustine Lighthouse to reach the observation deck. The wide view from the top makes every step worth it. Visit the Alligator Farm to meet sloths and gators. Thrill seekers can try the Nile River zip line course.
Summer also calls for sandy toes and salty breezes. St. Augustine Beach offers long stretches of soft sand and warm waves. Anastasia State Park is perfect for a picnic or an epic sandcastle build. And nearby ice cream shops make the sweetest ending to a beach day.
Hungry after exploring? The historic district is filled with top restaurants and lively cafes. Menus range from fresh seafood to Southern comfort food with a twist. Try a waterfront spot for blackened shrimp tacos. Or choose a candlelit courtyard for a cozy dinner. Many eateries are inside restored buildings, so your meal comes with history.
Pro tip: Make reservations for weekend evenings.
Plan Your September Getaway to St. Augustine
The Sing Out Loud Festival is more than a concert series; it’s a citywide celebration of music. This particular festival fills St. Augustine with performances, coastal charm, and unforgettable energy every September. Make your trip complete when you book a stay at one of our inns. Each offers a unique style, warm hospitality, and a location near the best music, dining, and attractions. Your perfect St. Augustine getaway is only a reservation away. Book today!
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