St. Augustine: Where History, Southern Hospitality and the Stories Behind the Songs Come Together
From the charm of the historic district to intimate performances by Nashville’s accomplished songwriters, the St. Augustine Songwriters Festival offers another reason to fall in love with America’s oldest city.
There is something special about St. Augustine. Perhaps it is the centuries of history woven into its streets, the character of its historic buildings, the welcoming people, or the feeling that there is always another hidden gem waiting to be discovered. Spend time wandering through the historic district & Colonial Oak Music Park, stopping for a drink at Tradewinds Lounge, enjoying a meal at Prohibition Kitchen, or simply taking in the atmosphere, and it is easy to understand why visitors return again and again.
For music lovers, however, there is another reason to put St. Augustine on the travel calendar: the St. Augustine Songwriters Festival, a celebration of the talented people behind the songs we know, love and sometimes don’t realize we know by heart.
The Man Behind the Music
The festival was founded by professional country songwriter and producer Arlis Albritton, whose own journey to Nashville began with little more than a dream and the determination to pursue it.
Before the festival became a gathering place for accomplished songwriters and music fans, Albritton was a young songwriter trying to find his footing in Nashville in 1994. Following his passion, he lived in his car for several weeks while chasing the opportunity to build a career. As he recalled, there was one gas station that didn’t lock its doors, giving him a place to freshen up.
It was not an easy beginning, but it was the kind of experience that taught him perseverance, the importance of relationships and what it means to believe in a dream before anyone else does.
He began frequenting the places where songwriters gathered, meeting people, building friendships and learning from those around him. His first major breakthrough came after he began working for Rick Hall at FAME Publishing. Finding the courage to ask another songwriter to write with him helped set the course for his career.
Following his first cut in 2001 when Diamond Rio recorded one of his songs, Albritton signed his first publishing deal with EMI. He continued writing, networking and returning to places such as the Key West Songwriters Festival, where he developed relationships that helped him grow as a writer.
Those experiences would eventually inspire him to create something of his own in St. Augustine.
A Festival Where the Songwriters Are the Stars
The original idea for the St. Augustine Songwriters Festival grew out of Albritton’s experience helping Charlie Bauer with the Key West Songwriters Festival. Bauer introduced Arlis to Dylan Rumrell, and Bauer encouraged him to take the St. Augustine concept and run with it.
The festival officially began in 2017, built around a simple but meaningful idea: make the songwriters the stars.
Albritton wanted to bring Nashville’s accomplished songwriters to St. Augustine and give audiences an opportunity to hear the stories behind the music directly from the people who created it.
As he explained, many music fans don’t realize that major recording artists don’t always write their own songs. The songwriter’s contribution can be every bit as fascinating as the performance that eventually reaches the radio. Behind a familiar chorus may be a personal experience, a memory, a heartbreak or a moment of inspiration that completely changes how you hear the song.
At the festival, the audience gets to experience that connection firsthand.
The main focus is country music, the genre Albritton has worked in professionally since 2001. But the appeal goes beyond musical style. It’s about storytelling, personality and the ability to connect with an audience.
Albritton remembers bringing in Mac McAnally before Jimmy Buffett’s passing, an experience that reflected the laid-back, welcoming spirit he wanted the festival to embody. In St. Augustine, he has found that the character of the songwriters can mesh beautifully with the character of the town he fell in love with visiting when he was younger.
A great song isn’t simply performed. It tells a story, draws the audience in, shares a laugh, and creates a moment that stays with people long after the music ends.
That is what makes these performances different from an ordinary concert: the songwriter behind the music.
The Stories Behind the Songs
One of the most memorable stories Albritton has witnessed at the festival involved songwriter Justin Wilson and a song he wrote about the grandparents who raised him.
Wilson explained the personal story behind the song before performing it. The connection between his memories, his words and his delivery moved the audience so deeply that, as Albritton recalled, there wasn’t a dry eye in the room.
That is the magic of a songwriter’s performance. You aren’t simply hearing a song; you’re being invited into someone’s life.
These moments remind us that songwriting is much more than a flash of creative inspiration. As Albritton pointed out, it is a job that can demand work from nine in the morning until whenever the day finally ends. It takes persistence, discipline, collaboration and a willingness to keep creating even when success feels far away.
When you hear the story behind a song, you begin to appreciate the work that happens before a recording artist ever steps into a studio or takes a stage.
And when you have the chance to speak directly with the person who wrote it, the experience becomes even more meaningful.
A Festival Built on Community
What makes the St. Augustine Songwriters Festival particularly special is that it remains free to the public.
Keeping the performances accessible has always been an important part of Albritton’s vision. The festival is designed to bring people into the community, particularly visitors who might not otherwise discover St. Augustine during a traditionally slower month.
The result benefits more than music fans. Local bars, restaurants, shops and hotels receive additional foot traffic, while venue owners contribute their spaces and help make the festival possible.
Albritton is quick to recognize that the festival would not exist without the community behind it. Sing Out Loud helps fund the event and keep it free, while Bozard Ford is the largest supporter. The generosity of participating venue owners is another essential part of the festival’s success.
That collaborative spirit reflects the character of St. Augustine itself: a town where local businesses, residents and visitors can come together around something they love.
The festival has grown organically since its first year, evolving from a creative idea shared by Albritton and Dylan Rumrell into an event that returning songwriters and devoted fans look forward to attending.
Some performances are intentionally unannounced, creating the possibility of an unexpected musical discovery. Occasionally, the festival also offers low-cost, ticketed shows in more intimate settings, such as a performance at the Distillery featuring Clint Daniels and other songwriters. These smaller shows allow audiences to hear the stories in an especially personal environment while keeping the cost manageable.
Albritton recently added two locations, with plans to grow gradually rather than lose the intimate atmosphere that makes the festival distinctive.
The venues are small, and space is limited. That closeness is part of the appeal, but it also means that popular performances can fill up quickly.
My advice: arrive early, find a seat, and give yourself time to enjoy the experience.
From Nashville Friends to No. 1 Songwriters
When Albritton began bringing songwriters to St. Augustine, many were friends he had met through his Nashville career. Over time, some went on to become No. 1 songwriters, and the festival continued to grow alongside their success.
Today, he is proud that songwriters reach out asking to participate and that many return year after year. They tell him how much they enjoy the organization, the audience and the city itself.
He also makes a point of incorporating local talent, including Davis Loose and Elis Mosley, whose careers have continued to develop through opportunities such as the festival.
For Albritton, selecting performers is not simply a matter of filling a schedule. There are limited slots in small venues, and the first priority is to bring in songwriters with recognizable hits that will draw fans. From there, he considers the other writers who will contribute to the festival’s atmosphere and overall experience.
Sometimes the decision comes down to the feeling and energy he wants to preserve.
His goal is to keep the festival family-friendly, welcoming, and personal while making room for new voices and future growth.
Why Songwriters Should Make the Trip
“As a songwriter myself,” said Albritton, “I understand how important relationships and networking can be in building a career. My own breakthrough came through the connections I made with other writers, and I know how much can change when you find the right person to collaborate with.”
That is one of the reasons I appreciate what Albritton has created.
His advice to aspiring songwriters is practical: if you cannot make it to Nashville, come to St. Augustine. Attend the festival, listen closely, introduce yourself, ask questions and learn how other writers approach their craft.
Do your homework. Understand who the songwriters are and what they have written. Take advantage of the opportunity to hear how a song came together, what inspired it and how the writer developed the idea. Many songwriters are happy to answer thoughtful questions.
Most importantly, make genuine connections.
The festival offers a chance to see how music-industry relationships develop in a relaxed setting, without the pressure of trying to break into a room full of strangers in Nashville. For aspiring writers, it can be an opportunity to learn, build friendships and become part of a community that understands the creative process.
Albritton knows firsthand how important those connections can be. The relationships he built throughout his career helped inspire the festival, and he hopes today’s songwriters will find similar opportunities through it.
He also hopes to see more writers bring their families and become part of the festival’s growing community.
Where to Stay: A Historic District Experience
During my visit, I stayed at the Renaissance St. Augustine Historic Downtown Hotel, which made an excellent base for exploring the city and attending the festival. Its location within walking distance of the festival venues meant I could leave the car behind and enjoy the historic district on foot.
That is one of the pleasures of visiting St. Augustine. You can build an entire day around walking, discovering charming streets, browsing shops, stopping for a meal or drink and finding a new favorite spot along the way.
Harry’s is a great addition to your itinerary, offering a chance to enjoy the local atmosphere between performances.
Even without a festival schedule, the historic district is worth exploring at a relaxed pace. Take time to appreciate the architecture, learn about the city’s history, talk with local business owners and enjoy the welcoming spirit that makes St. Augustine so memorable.
Then let the music become part of the adventure.
Why St. Augustine Belongs on Your Travel List
The St. Augustine Songwriters Festival has grown from an idea shared among friends into a community-driven celebration of music, storytelling and connection. But Albritton is clear that the festival is a bonus to what makes the city so special.
He wants visitors to discover St. Augustine as a whole: its history, its character, its people and its ability to make you feel welcome.
I couldn’t agree more.
Whether you are a country music fan, an aspiring songwriter, a traveler who loves historic destinations or simply someone looking for a memorable Florida getaway, St. Augustine offers a wonderful combination of experiences. You can spend the morning exploring centuries of history, enjoy lunch in the historic district, wander through local shops, settle in for an afternoon of live music and finish the day sharing a meal or a drink with friends.
And if you visit during the St. Augustine Songwriters Festival, you may find yourself hearing a familiar song in an entirely new way.
The festival is free, the performances are intimate, and the stories behind the songs can be unforgettable. Because the venues are small, arriving early is worthwhile, especially if there is a songwriter you particularly want to hear.
My recommendation? Put St. Augustine at the top of your list. Come for the history, stay for the hospitality, explore the local restaurants and lounges, and let the music be the unexpected highlight of your trip. You may arrive as a visitor, but between the charm of the historic district and the stories shared by the songwriters, you just might leave feeling like part of the community.
The St. Augustine Songwriters Festival is a reminder that the best travel experiences are not always about checking landmarks off a list. Sometimes, they are about discovering a place through its people, its stories and the songs that bring us together.
A special thank-you to Arlis Albritton, the participating venue owners, Bozard Ford and Sing Out Loud for helping make this festival possible and keeping the songwriter experience accessible to the public.
