How a winter festival became a cultural force.
In the fall of 2009, a few friends gave longtime local and event producer Jennifer Steele an idea: Florida's Scenic Highway 30A should host a music festival. She developed the concept and pitched it to the board of the Cultural Arts Alliance of Walton County, where she had recently been named director.
It could be held in the winter, a time when the then-lightly populated stretch of beach was all but deserted. It would draw musicians and music lovers to the area during the slow season and serve as a fundraiser for the CAA. With no major music venue in the region, the artists could play at pop-up stages at restaurants and bars along the 19-mile stretch of coastal road and beach towns.
The following January, a motley crew of headstrong volunteers pulled it off. They enticed more than 80 artists, including the Indigo Girls, Rodney Crowell, and Jeffrey Steele, one of Nashville's hottest songwriters at the time. They created stages at a dozen locations, most of which did not exist before, including a makeshift main stage overlooking the dunes in Alys Beach. The 30A Songwriters Festival was born.
That first year, 800 tickets were sold. Seventeen years later, over 5,000 people attend each year, and the festival is stronger than ever, hosting major acts, longtime favorites, and rising stars from country, folk, blues, Americana, jazz, R&B, and alternative rock.
"I wish we could say we had some type of 20-year plan, but we really just had a group of passionate people. That first year, we pulled it off and were happy everyone had a good time. It wasn't until the second year that we really started to see the potential."
Where It All Began
These days, when a popular tune is created by purchasing a song, recording it, producing it, and pumping it out to the masses via social media, the songwriters behind the music are often the unsung heroes of the hits. The festival set out to celebrate those writers and anyone whose craft involves taking a blank space in the world and filling it with sound and story. While the main stage can accommodate thousands, most venues hold between 200 and 1,000 guests, offering a far more intimate concert-going experience.
"Songwriters are the heart and soul of the music industry," said Russell Carter, who co-produces the festival with Steele. "In our minds, it's a profound experience to walk into a venue with 200 people up close and personal and hear an artist who has written a song tell the story of why they wrote it, what it means to them, and then hear them perform it."
Finding the Rhythm
In just two months, Steele and the volunteers, learning on the job in a labor of love, hobbled together a modest budget of $8,000, gathered a roster of performers, sold the concept to local restaurants and major resorts, marketed it to fans, schlepped tickets, and organized how it would all come together at showtime.
One of the group's first calls was to Carter, who owns his own artist management company. He happened to be vacationing in Grayton Beach at the time. He was intrigued and offered to meet for coffee. "I just happened to be in the right place at the right time, vacationing," he said. Having caught the bug, he started calling in favors to artists he knew, selling them on the concept of playing at a secluded beach in the dead of winter.
There was a learning curve. At Fish out of Water in WaterColor, the staff brought out their fine wine glasses for the festival. "We broke about half," Carter said. The following year, they converted to plastic.
The temporary stage constructed at Alys Beach for the Indigo Girls was beautiful, but unexpectedly strong, frigid winds blew Gulf water over the dunes and onto the equipment. The band delayed the show, huddled up in coats and scarves, but eventually threw off their gloves and played anyway to an ecstatic crowd. Today, main acts perform on a professionally constructed stage at Grand Boulevard, which can accommodate up to 6,000 people.
The first year's check-in and box office were held in a 200-square-foot hallway in Seaside, squeezed between the elevator and staircase. "That's just hilarious to me now," Steele recalled. Today, the box office is housed in a massive tent at Marina Park in WaterColor.
Where Art Pays Off
By 2019, the last year the Walton County Tourist Development Council gathered this data, what had once been a little beachside festival was generating over $8 million in economic impact. That number has only grown, Steele said.
"The festival is a perfect example that investing in art and culture is actually a sound financial decision. Nobody goes into the arts thinking, let's make a lot of money for the community, but they should. Because it works."
"All of a sudden, the dead month became a very active and profitable business," Carter said. "Sixteen years later, it's hard to even see traces of a shoulder season anymore."
The Cultural Arts Alliance has grown along with it. It now produces the country's only Underwater Museum of Art, a prison art initiative, dozens of festivals and events, and year-round programs for kids and adults. When the festival began, the organization had one part-time staff member. Today it employs eleven.
From Openers to Icons
Now, when Carter calls artists about attending, everyone already knows about the festival and the 30A area in general. Usually, the artists call him. They've landed Tanya Tucker, Brian Wilson of The Beach Boys, Jackson Browne, John Prine, Lyle Lovett, Emmylou Harris, Graham Nash, Lucinda Williams, and Cheap Trick.
Plenty of newcomers also play each year, often tucked into lineups at smaller venues, and many have seen their careers take off since. Brandi Carlile played in 2019 as she was quickly becoming a nationally recognized artist. Jason Isbell played as a relatively unknown artist launching his solo career; when he returned several years later, he was a headliner and a three-time Grammy winner. And perhaps the biggest rise: Meghan Trainor, the high schooler who came down years ago with her mother to play guitar and perform her original songs, is now a chart-topping pop powerhouse.
When Prine played in 2020, he was 73. He performed on the main stage, but he also played a smaller show, and it was a rare moment that Steele was able to sit still and listen to an entire performance. "I was pinching myself and crying a little bit, smiling and laughing. It was just so special." Less than three months later, Prine passed away from complications from COVID, making the performance one of his last.
One of Carter's favorite moments was seeing Jackson Browne, an artist he grew up listening to. "I taught myself guitar by playing his songs." In 2016, at 67, Browne agreed to play and decided to turn it into a small tour. He pulled up to the main stage with a truck and trailer and unloaded a collection of guitars and a grand piano, then played solo acoustic, moving between guitars and the piano for each song. "He played every great hit. I mean every single one of them. It was just a phenomenal concert."
Feels Like Home
Mavis Staples, a legendary singer from a legendary musical family, headlines this year's festival at 86. For the first time, a Friday afternoon kickoff event will be held at the Seaside Amphitheater, featuring Margo Price. Other artists of note include Benmont Tench, the keyboard player from Tom Petty and the Heartbreakers, Amy Helm, Jonatha Brooke, and Joseph Arthur.
Robin Beans volunteered that first year and has worked artist check-in ever since. Every time an artist came to check in, she would run outside, around the corner to The Rep Theatre, to grab their supplies. She brought her own snacks to share. Even though she's moved away, she will return again this year. "I'm never leaving unless they kick me out or I become too old to do this," the 69-year-old said.
Many artists return year after year. Beans said she knows they love the beautiful beaches, but she's also heard that other festivals just aren't as friendly. A getaway in the dead of winter has become a beloved tradition for both fans and the artists performing for them.
"I try hard each year to make it feel like a welcome back. A welcome home."
Stay in tune with this year's artists, updates, and ticket info at 30ASongwritersFestival.com.
Photos: Nathan Zucker, Shelly Swanger, Evan Carter, Troy Ruprecht, Lynn Crow and Tommy Crow.
This story appears in Beach Happy Magazine, Issue No. 23 (Winter 2026). Read the full issue here.
