Hilton Head is just magic,” said David Preston, leaning into the words with an easy conviction that comes from decades of seeing music transform places – and people. After 30 years with BMI and a life spent alongside songwriters (his mother was president of BMI), Preston knows better than most how a festival can breathe new life into a community.
Come September 18-21, Preston and his team will bring the Hilton Head Island Jam Songwriter Festival into its third year, transforming the island into a haven for hitmakers, local artists, and music lovers who crave more than big stage shows. They want the story behind the song.
LOCASH performs at last year’s event at Lowcountry Celebration Park
“Everyone in Nashville … you mention Hilton Head – they’ve been there, they love it,” Preston said. “It’s a great place without being over-commercialized, and without trying to be. Hilton Head has its own unique, pristine, distinctive identity and that’s why everyone loves it.”
The seeds for the festival were planted in 2022, when Preston got a call from Reid Perry, a longtime island resident whose son is a songwriter. Could Preston help create something that blended Hilton Head Island’s coastal charm with Nashville’s songwriting soul? The answer was obvious.
“It just made great sense,” Preston said. “The people in Hilton Head love the songwriters, and the songwriters love being in Hilton Head. It’s synergy – and the response we’ve gotten has been tremendous.”
That synergy is more than tourist appeal. It’s a carefully curated balance between big Nashville names and intimate Lowcountry venues, creating something uniquely Hilton Head.
Alyson Nichols and Brett Jones
“Songwriter festivals have popped up everywhere, but it’s really about location and vibe,” Preston said. “Hilton Head has this Celebration Park … it’s a perfect stage. The island has enough venues to bring in a good crowd without feeling overwhelming.”
Bobby Magyarosi performs at the Tiki Hut
From Key West to the Carolinas
While the local festival is still young, Preston’s vision draws on deep experience. In 1996, he helped launch the now-legendary Key West Songwriter Festival, which grew from eight songwriters to more than 130. He has also been part of Colorado’s Country in the Rockies and Florida’s Port St. Joe festival.
“At Key West, we block off Duval Street, have thousands of people, and headline acts like LoCash,” Preston said. “But Hilton Head isn’t trying to be that. It’s about intimacy, storytelling, and connections.”
That history matters. It taught Preston the value of curating shows where Nashville’s hitmakers meet new voices – and where every venue adds its own character.
Kyle Wareham and Nick Poulin of Pretty Darn
“Location matters. People don’t go to Key West for the beach; they go for the bars, the streets, the energy,” he said. “Hilton Head has its own rhythm, with its restaurants, Lowcountry Celebration Park, the Liberty Oak, and even the Westin pool deck.”
For 2025, the lineup promises both star power and fresh discovery. Headlining Saturday night in the park will be the chart-topping duo LoCash, whose ties to the festival run deep.
“They came the first year, played golf, fell in love with the island,” Preston said. “Now we do the LoCash Golf Bash – it opens the door for their friends to come play, too.”
Other highlights include Jeffrey Steele, one of the top five most-performed country songwriters, whose hits include “My Wish” (Rascal Flatts) and “The Cowboy in Me” (Tim McGraw); Earl Bud Lee, who co-wrote “Friends in Low Places”; classic country’s Deborah Allen; rising stars like Justin Wilson and George Ducas; and second-generation talents like Casey Beathard’s son, Tucker Beathard.
LOCASH rocks the stage at last year’s Hilton Head Island Jam Songwriter Festival
“It’s mostly contemporary country, but we’ve also got Jeffrey Steele’s daughter bringing her duo partner. They perform as Silence and Noise,” Preston said. “And Casey Beathard’s son Tucker is an incredible songwriter himself.”
If the festival’s public face is concerts, its backstage magic is in the connections Preston orchestrates.
“I’m like a matchmaker,” he said. “I know these songwriters, but they might not know each other. After a weekend in Hilton Head, they leave with new co-writing partners. That’s my favorite part.”
This synergy extends to local artists, too. Thanks to a partnership with Swamp Fire Records, the festival includes six local performers each year.
“We have this self-imposed mandate,” Preston said. “Local talent shares the stage with Nashville pros. It’s networking, mentorship, and sometimes life changing.”
Taylor Kent
For example, Alison Nichols, whose father lives on the island, played the first year, and soon after, she signed a record deal. “She’s grandfathered in now,” Preston said. “No matter how big she gets, we’ve got her.”
The Venues
With 23 shows scheduled at this writing, the festival spans intimate bars, park stages, hotel decks, and more. Big Bamboo, the outdoor stage at FISH, The Jazz Corner, and Liberty Oak each offer a different vibe.
“The park closes at 10 p.m., so we move from there to Big Bamboo, or to late shows at the Westin,” Preston said. “It’s tricky to avoid overlaps, but the variety keeps it fresh.”
Signature events include: Harbour Town Throwdown under the iconic Liberty Oak; Smooth Sailing at The Jazz Corner, featuring Angie Aparo and others; Coligny Sessions on the pond stage; The Porch at Beach House; The Westin Song Splash by the pool; Date Night Dinner & Show and Laid-Back Lunch at the Westin; Bluebird at the Bamboo early shows; and Big Bamboo late shows.
“The Bamboo late-night shows are always a hit,” Preston said. “It feels like Nashville, but with that island breeze.”
While intimacy is part of the festival’s charm, Preston sees room to grow. “I’d love to move a larger show to Honey Horn,” he said. “Create a ticketed, headline act – something like what we do in Key West, where we had 30,000 people for LoCash last year.”
That growth isn’t about losing the festival’s character, but about celebrating it on a bigger scale. “Imagine blocking off Pope Avenue for a huge show,” Preston said. “It sounds crazy, but why not?”
At the heart of it all is a simple truth: Songwriters rarely get the spotlight, but they create the soundtracks to our lives.
“If you wanted the artist who recorded the song, it’d cost 10 times more,” Preston said. “But when you hear it from the person who wrote it, you hear it the way they envisioned it. It’s raw, honest – and sometimes a little out of tune – but that’s part of the beauty. Songwriters might not all be world-class singers, but the audience gets the story, the emotion, the why behind the words.”
Free, Open & Local
A defining feature of the Hilton Head Island Jam is its accessibility. “This is a free event,” Preston said. “Some dinner shows at the Westin require reservations, and some venues might have a small cover but, by and large, you’re getting world-class talent at no cost.”
That inclusivity, supported by the town and local businesses, keeps the festival grounded in community. “It’s basically a celebration for surviving summer,” Preston said with a chuckle. “A chance for locals and visitors alike to gather, relax, and listen.”
For those dreaming of the Nashville scene, Preston offers heartfelt advice: “Be part of the community,” he said. “Show up, share your work, and build relationships. A single connection with a professional songwriter can be invaluable.”
This festival creates those opportunities, even if sometimes through what Preston calls “the back door.”
“It’s networking but not forced. It’s jamming, laughing, writing – and if you’re open, you might leave with a co-writer, a mentor, or a breakthrough.”
When asked to sum up the festival in four words, Preston paused, smiled, and said simply: “Living on Carolina Time.”
Perhaps that’s the festival’s true legacy: underscoring South Carolina’s love for music, for the island, and for the unseen writers whose words move us.
Whether you’re a devoted fan, a casual listener, or an aspiring songwriter, this year’s festival promises something timeless: music that tells a story, shared under Lowcountry skies.
If You Go:
September 18-21
Lineup highlights: LoCash, Jeffrey Steele, Earl Bud Lee, Deborah Allen, Silence and Noise, Tucker Beathard, and more.
Venues: Celebration Park, Big Bamboo, Jazz Corner, Liberty Oak, FISH, the Westin, Lincoln and South Brewery.
HiltonHeadIslandJam.com
