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

During my inaugural evening in St. Augustine, Florida, I explored the vibrant music scene by moving seamlessly from one intimate venue to another: starting at Hornski's Brewing Company for a performance by Chemtrails, then heading to Sarbez! where Ghost Tropic was playing. Each location offered its own unique ambiance and audience.

I was attending the Sing Out Loud, an annual festival dedicated to the celebration of local and regional music, which proudly reached its 10th anniversary in 2026. Over the course of the September showcases, more than 100 local artists performed throughout the city, highlighting various genres such as indie rock, bluegrass, country, jazz, and Americana.

In addition to the music, I explored various galleries, the city's prominent concert venues, and notable historical sites. Despite their diverse offerings, they collectively contributed to the cohesive, colorful, and slightly quirky essence of a city steeped in centuries of history—all neatly contained within a few walkable blocks.

Sing Out Loud: Free shows across the city

The Sing Out Loud showcases are complimentary and spread across a variety of bars, breweries, restaurants, and outdoor stages, transforming the festival into an experience of discovery within the city. My Saturday evening commenced at Hornski's Brewing Company, which features two entrances resembling old garage doors that open to a lively pool table area adorned with a mural depicting St. Augustine. Chemtrails captured the attention of a youthful, laid-back crowd. I appreciated the extensive selection of non-alcoholic beverages, especially since I was still recovering from a recent wine-filled trip to Italy.

I arrived at Sarbez! just before 8:00 PM, coinciding with the transition from a family-friendly atmosphere to an adults-only environment. While families enjoyed the upbeat guitar riffs and children reveled in grilled cheese sandwiches and fried pickles alongside arcade games, the venue shifted to allow those 18 and older until 10:00 PM and then 21 and older afterward. The crowd was notably lively by the time Ghost Tropic took the stage.

Later that night, back at the AC Hotel St. Augustine Downtown, I found it difficult to sleep. An unfamiliar creaking near the bathroom echoed through the room, reminiscent of someone shifting their weight, while a persistent luminous ring around the television cast a pale glow in the darkness, much like a ghostly moon. I attributed my restlessness to the day's experience with Ghost Tropic and the prevalent conversation about ghost tours in town.

By Sunday afternoon, propelled by minimal sleep, I abandoned my planning and simply followed the music. This led me to Bin 39, a wine bar located in the St. George Inn, conveniently positioned steps away from the Old City Gates, built in 1808. Banjo Brown played, and after their set, I ventured south on St. George Street and turned onto Hypolita Street towards Casa Maya, predominantly attracted by its name. I opted for a straightforward selection of veggie tacos and guacamole, as another show awaited me.

My next stop was Colonial Oak Music Park, a charming outdoor venue that resembles a cabin nestled in the woods. It features an expansive area shaded by what the owners proudly claim is a 300-year-old oak tree, creating a festive, Oktoberfest-like atmosphere. The crowd here was notably older and more polished compared to Hornski's, as Sparks in the Garden serenaded us, and I felt the heaviness of the humidity clinging to my shirt.

The remainder of the weekend unfolded similarly: I would venture out for coffee and find myself exploring a vintage shop. On a particularly hot day, indulging in a pineapple-orange pop from The Hyppo Gourmet Ice Pops proved to be a delightful diversion. A stroll down an inviting historic street would often culminate in a spontaneous stop at a bar where live music was playing. Opting to forgo the Old Town Trolley, I walked and relished the music spilling out from doorways, appreciated the various courtyards and wrought-iron balconies, and observed the architecture shift with each block. The historic district is best experienced on foot, as its streets were designed in a grid formation around the Plaza de la Constitución, which remains the heart of the old town.

Beyond the festival: St. Augustine's concert venues

St. Augustine's vibrant live-music culture extends beyond the festival's span. On my final morning, I had the opportunity to speak with Ryan Hall, the Chief Marketing and Communications Officer for the St. Augustine Amphitheatre and Ponte Vedra Concert Hall, who provided insight into the region's primary music venues.

Ponte Vedra Concert Hall was originally constructed in 1980 as the Palm Valley Baptist Church and community center. It was acquired by St. Johns County in 2006 for $9.2 million to preserve it as a public cultural space and reopened as a concert venue in 2011. Following a 14-month, $12.9 million renovation inspired by audience demand for a balcony, the grand reopening on August 1, 2025, featured the Dan Tyminski Band. The newly expanded facility increased its size from approximately 10,500 to 25,500 square feet, offering flexibility with 615 seats for theater-style performances and around 1,100 standing for others, supported by a state-of-the-art L-Acoustics sound system and upgraded lighting.

Backstage, the dressing rooms exude a nostalgic charm, filled with vintage 1950s refrigerators that evoke a sense of stepping onto a classic film set. Downstairs, the concession stand serves a vegan kimchi hot dog that piqued my curiosity. Despite its growth, the stage remains close enough for the audience to feel a genuine connection to the performers, which explains why artists like Melissa Etheridge and the Steep Canyon Rangers are drawn to this venue.

The St. Augustine Amphitheatre, referred to as The Amp, is the larger of the two venues. Its open-air stage has hosted an impressive lineup of artists that reads like a music history playlist, featuring legends such as John Legend, Bob Dylan, Aretha Franklin, Ringo Starr, Rod Stewart, Robert Plant, and Stevie Nicks. Comedians, including Tom Segura and Nikki Glaser, have also graced its stage. Despite its size, the setting maintains an intimate atmosphere, surrounded by the lush greenery of Anastasia State Park. The experience of attending a concert beneath a canopy of trees, rather than in a sterile concrete environment, adds a uniquely Floridian touch. The venue also hosts a farmers market on Saturdays, showcasing local produce, prepared foods, and handmade goods.

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

I spent an afternoon leisurely exploring Uptown San Marco, where the main entrance of Castle Warden caught my eye. This impressive Gilded Age mansion, built in 1887, boasts a striking Moorish Revival architecture and now houses the Ripley's Believe It or Not! Museum. In the 1940s, it operated as a hotel run by Norton Baskin, whose wife, Pulitzer Prize-winning author Marjorie Kinnan Rawlings, resided there, and it has gained a reputation as one of Florida's most haunted locations. Continuing north along San Marco, I encountered Spinster Abbott's, a unique establishment offering vintage furniture, art, and eclectic décor, along with coffee, beer, and wine, creating a distinct aesthetic throughout the space.

As I continued my walk, I noticed the Florida School for the Deaf and the Blind, an impressive institution characterized by its Mediterranean-style architecture spread across a vast campus. Founded in 1885, it is the largest of its kind in the country, comprising 47 buildings across more than 80 acres. Although it is an active school, its stunning grounds are worth admiring from the outside.

For those seeking art galleries, Aviles Street—the oldest street in the city and the heart of its arts district—is lined with an array of galleries showcasing painting, photography, sculpture, jewelry, and works by Florida artists. For a more comprehensive museum experience, the Crisp-Ellert Art Museum located on the Flagler College campus features contemporary artists from regional, national, and international backgrounds, all within one of the city's most historic environments.

Before and after 1565: St. Augustine's history

Founded in 1565 by Pedro Menéndez de Avilés, St. Augustine holds the distinction of being the oldest continuously inhabited European-established settlement in the continental United States—predating Jamestown by over 40 years and Plymouth by more than 50.

To grasp the significance of this history, a visit to the Fountain of Youth Archaeological Park is essential. While the name invokes the enchanting allure of Florida mythology, the archaeological evidence is very real. The park marks the site of the Timucuan village of Seloy, where Menéndez claimed the territory for Spain in 1565, and excavations have revealed indicators of both Spanish presence and earlier Indigenous habitation.

The Timucuan people merit more than just passing acknowledgment. Spanish missionaries established a network of missions within Timucuan communities, introducing Catholicism and European customs along with new labor and settlement practices. The Indigenous population faced devastating losses due to disease, compounded by warfare and colonial disruptions. By the late 17th and early 18th centuries, the Timucuan population significantly dwindled, and their language ultimately vanished. The beauty of the city exists concurrently with these narratives.

A separate yet equally significant story emerged in 1738, when Spanish authorities founded Gracia Real de Santa Teresa de Mose, commonly known as Fort Mose, a legally recognized free Black community situated north of the city. Its residents included individuals who escaped enslavement from the British colonies. Fort Mose deserves its place on any culturally aware St. Augustine itinerary and ties back to the music scene, as the annual Fort Mose Jazz & Blues Series in February connects contemporary sounds to the legacy of one of America's earliest free Black communities.

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

The AC Hotel presents a modern counterpart to St. Augustine's historic coquina architecture, providing a comfortable place to unwind after a day spent exploring centuries-old streets and intimate music venues. Situated along the San Sebastian River, it is conveniently located about a 10-minute walk from Flagler College and the historic district.

For those planning a visit centered around music, be sure to mark September for the complimentary local showcases of Sing Out Loud. (As a note, the festival's major Francis Field Showcase is set to move to May starting in 2027.) If you prefer winter trips, February offers the Fort Mose Jazz & Blues Series. Regardless of your scheduling, allocate two to three days for the experience and resist the urge to treat St. Augustine as merely a one-day stop for historical sites.