St. Augustine’s Sing Out Loud Festival Is a Free Ticket to the City’s Arts Scene

On my first night in St. Augustine, Florida, I chased music from one small room to the next: Hornski’s Brewing Company for Chemtrails and Sarbez! for Ghost Tropic. The bands, rooms, and crowds were all different.

I was in town for Sing Out Loud, the annual celebration of local and regional music that marked its 10th anniversary in 2026. More than 100 local artists played across the city during the September showcases, from indie rock and bluegrass to country, jazz, and Americana.

Over the weekend, I also visited some of the city’s galleries, its two biggest concert venues, and a few of its historic sites. Those were different, too, but it all felt like the one colorful, slightly eccentric city, with centuries of history packed into a few walkable blocks.

Sing Out Loud: Free shows across the city

Sing Out Loud’s showcases are free and scattered through bars, breweries, restaurants, and outdoor stages, so the festival becomes a way of moving through the city. My Saturday night started at Hornski’s Brewing Company, where two entrances that look like old garage doors open onto a pool table and a mural of St. Augustine. Chemtrails played to a young, edgy, come-as-you-are crowd. The beer list had a good run of non-alcoholic options, which suited me. I was still on a break after a wine-soaked trip to Italy.

I reached Sarbez! before 8:00 PM while the kids were still running the place. Families nodded along to the guitar riffs, and the kids, fueled by grilled cheese and fried pickles, worked their way through a seriously deep lineup of arcade games. Then 8:00 PM hit, and the little ones were cleared out for adults-only play time: 18 and over until 10:00 PM and 21 and over after that. By the time Ghost Tropic took the stage, the crowd was robust.

Later, back at the AC Hotel St. Augustine Downtown, I couldn’t sleep. Something near the bathroom kept creaking, slow and spaced out, like someone shifting their weight, and I lay there counting the gaps. The television had a ring of light around the screen that wouldn’t switch off, so it hung in the dark like a pale moon. I blame the day: a band called Ghost Tropic, plus everyone in town talking about ghost tours and haunted buildings.

By Sunday afternoon, running on little sleep, I had stopped planning and started following the sound. It led to Bin 39, the wine bar in the St. George Inn, whose courtyard sits steps from the Old City Gates at the north end of St. George Street. The gates’ coquina pillars went up in 1808.

Banjo Brown played. When the set ended, I walked south on St. George Street, then turned onto Hypolita Street to Casa Maya, which I chose mostly on the name. I kept it simple with veggie tacos and guacamole, with a show still ahead of me.

Then came Colonial Oak Music Park, which looks like a cabin you’d stumble on deep in the woods. The outdoor venue sits beneath what the owners bill as a 300-year-old oak, and the mood leaned toward Oktoberfest. The crowd skewed older and more buttoned-up than the one at Hornski’s. Sparks in the Garden played acoustic rock into air so heavy with the day’s humidity that my shirt had surrendered and clung to my back.

The rest of the weekend went about the same way. I’d head out for coffee and end up in a vintage shop. On a sweltering day, a pineapple-orange pop from The Hyppo Gourmet Ice Pops was the best detour of the trip. A walk down a historic street ended at a bar with a band. I skipped the Old Town Trolley and walked, which meant hearing music drift out of doorways, noticing courtyards and wrought-iron balconies, and watching the architecture shift block by block. The historic district is best seen on foot. Spanish colonial planners laid its streets out in a grid around the Plaza de la Constitución, and the plaza is still the center of the old town.

Beyond the festival: St. Augustine’s concert venues

St. Augustine’s live-music culture doesn’t disappear when the festival does. On my last morning, Ryan Hall, the chief marketing and communications officer for the St. Augustine Amphitheatre and Ponte Vedra Concert Hall, walked me through the region’s two anchor venues.

Ponte Vedra Concert Hall was built in 1980 as the Palm Valley Baptist Church and its community center, bought by St. Johns County in 2006 for $9.2 million to keep it a public cultural space, and reopened as a concert venue in 2011. Then came a 14-month, $12.9 million overhaul, sparked by a fan-led push to add a balcony. The grand reopening on Aug. 1, 2025, with the Dan Tyminski Band, unveiled a footprint that had grown from roughly 10,500 to 25,500 square feet. The room now works two ways: 615 seats for a theater-style show, or roughly 1,100 standing when the floor chairs come out, backed by a high-end L-Acoustics sound system and upgraded lighting.

Backstage, the dressing rooms are little time capsules, stocked with 1950s refrigerators that make you feel like you’ve wandered onto the set of Leave It to Beaver. Downstairs, the concession stand sells a vegan kimchi hot dog I desperately wanted to try. And for all the growth, the stage still feels close, so everyone in the house gets an intimate look at who’s performing. Hall told me that closeness is why musicians and comedians love it. Melissa Etheridge and the Steep Canyon Rangers are among those who have played it.

The St. Augustine Amphitheatre, known as The Amp, is the heavyweight. The artists who have played its open-air stage read like a music-history playlist: John Legend, Bob Dylan, Aretha Franklin, Ringo Starr, Rod Stewart, Robert Plant, and Stevie Nicks. Comedians come through too, including Tom Segura and Nikki Glaser. But the setting keeps it from feeling like an arena. The venue is surrounded by the greenery of Anastasia State Park, and there’s something wonderfully Floridian about seeing a major act under a canopy of trees instead of between concrete and parking garages. On Saturdays, it also hosts a farmers market with local produce, prepared foods, and handmade goods.

San Marco Avenue to Aviles Street: St. Augustine’s art scene

I spent an afternoon drifting through Uptown San Marco. Along San Marco Avenue, the main entrance of Castle Warden stood out: a heavy arched doorway on a Moorish Revival mansion, built in 1887 as a Gilded Age winter retreat and now home to Ripley’s Believe It or Not! Museum. In the 1940s, it was a hotel run by Norton Baskin, whose wife, Pulitzer Prize-winning The Yearling author Marjorie Kinnan Rawlings, lived there, and it carries a reputation as one of Florida’s most haunted buildings. Farther along, Spinster Abbott’s anchors the neighborhood, selling vintage furniture, art, eclectic décor, coffee, beer, and wine. It reads like one person’s aesthetic spilling across the entire space.

Keep walking north on San Marco and the Florida School for the Deaf and the Blind has the imposing charm of an old mansion scaled up to an entire campus. Mediterranean-style buildings rise behind broad lawns, their arches, columns, and shaded walkways lending the place an almost cinematic grandeur. This is a working school — founded in 1885 and the largest of its kind in the country, with 47 buildings spread across more than 80 acres — so admire it from outside.

For galleries, Aviles Street, the city’s oldest street and the heart of its arts district, is lined with them, showing painting, photography, sculpture, jewelry, and work by Florida artists. For something more museum-like, the Crisp-Ellert Art Museum on the Flagler College campus brings regional, national, and international contemporary artists into one of the city’s most historic settings.

Before and after 1565: St. Augustine’s history

St. Augustine was founded in 1565 by Pedro Menéndez de Avilés, making it the oldest continuously occupied European-established settlement in the continental United States. That’s more than four decades before Jamestown and more than five before Plymouth.

To feel what that means, go to the Fountain of Youth Archaeological Park. The name is pure Florida mythology, but the archaeology is real. According to the park, the land was the site of the Timucuan village of Seloy, where Menéndez claimed the territory for Spain in 1565, and excavations have turned up evidence of both the Spanish presence and earlier Indigenous habitation.

The Timucua deserve more than a footnote. Spanish missionaries built a network of missions among Timucuan communities, bringing Catholicism and European customs along with new systems of labor and settlement. Disease devastated Indigenous populations, and warfare and colonial disruption compounded the losses. By the late 17th and early 18th centuries, the Timucuan population had declined dramatically, and the language eventually disappeared. The city’s beauty exists alongside those stories.

So does a very different one. In 1738, Spanish authorities established Gracia Real de Santa Teresa de Mose, better known as Fort Mose, a legally sanctioned free Black community north of the city. Its residents included people who had escaped enslavement in the British colonies to the north. Fort Mose belongs in any St. Augustine itinerary that takes culture seriously, and it ties back to the music: the Fort Mose Jazz & Blues Series, held in February, connects contemporary sound to the history of one of America’s earliest free Black communities.

Planning around the music: When to go and where to stay

The AC Hotel is a sleek counterpoint to all of St. Augustine’s coquina, and after a day of centuries-old streets and small rooms, it’s a good place to land without being far from the action. It sits on the San Sebastian River, about a 10-minute walk from Flagler College and the historic district.

If you’re coming for music, circle September for Sing Out Loud’s free local showcases. (The festival’s big-name Francis Field Showcase moves to May starting in 2027.) For a winter trip, look to February and the Fort Mose Jazz & Blues Series. Whenever you go, give yourself two or three days and resist treating St. Augustine as a one-day historic-site stop.