Lyrics and Music Meet Sand and Sun at the Inaugural Destin Songwriter Festival

By Will Estell

If you’re a beach lover from near or afar and consider yourself a fan of music and the men and women that make it happen, you’re going to want to make plans to attend Destin’s first ever songwriter fest.

This October 10 and 11th, the white sands and emerald waters of the World’s Luckiest Fishing Village will also serve as the picturesque backdrop for the inaugural Destin Songwriter Festival, bringing together an array of talented songwriters and performers for a weekend of meaningful lyrics, great music and fun-loving music fans converging along the beautiful coastline.

Situated along Destin Harbor, the festival will feature everything from intimate acoustic sets to unforgettable headliner performances and offer a first-hand glimpse into the stories behind the songs. Fans will have the opportunity to feel every lyric and the weight each song carries in its journey to become a musical story.

In my two decades of covering festivals and writing feature cover story interviews on well knowns from Alan Jackson and Brian Kelley to Kenney Chesney, Darius Rucker, and the late great Jimmy Buffett, I’ve often said that to sing is one thing, but to write and breathe lyrical life into a song is quite another. Remarkably, the Destin Songwriter Festival offer attendees the opportunity to experience both. Whether you’re a lifelong music devotee, a casual festivalgoer or simply a beach lover looking for a soundtrack to paradise, this is where the art of songwriting meets the beauty of Destin.

I talked with organizer and Destin Songwriter Festival CEO, Matthew Pennings, who gave me a little insight into the festival and how the two-day event would run.

“Throughout the festival, music lovers can enjoy free performances at multiple popular venues along Destin Harbor, coupled with paid ticketholders being able to access the mainstage, and feature acts, just up the hill at 314 Harbor Blvd. These waterfront stages include popular Destin venues like Boat House, Sky Bar at Edge Seafood and Harbor Tavern. All of the shows in those venues will be free to attend, while the mainstage will be a ticketed, patrons-only area.”

The festival’s Main Stage at 314 Harbor Blvd. is where the weekend crescendos, with both general admission and VIP tickets available. Here fans will get up close with a premium production setup complete with drink and food vendors, along with world-class performances by such renowned writers and performers such as James Otto, Kent Blazy,and Andy Griggs. The three aforementioned not only for their stage presence, but for their hit songs gracing country radio and streaming playlists around the globe.

Supporting artists performing on the Destin Songwriter Festival Main Stage include Justin Holmes, Matt Wynn, Justin Andrews and Nashville recording artist, Jessie G –who also happens to be festival founder Matthew Pennings’ lovely and talented wife.

I asked my friend and fellow music lover, Destin Mayor Bobby Wagner, what the new songwriter festival means to him, and he gave it a resounding thumbs up.

“Our harbor area has always been the heart of Destin, and welcoming songwriters alongside our own local talent can really turn it into a stage that celebrates community and culture. As someone who loves music, just like you do, I see this festival as more than entertainment. It’s a chance for our locals to share their voices, and for our visitors and vacationers to experience the spirit of Destin through both song and the beautiful backdrops you mentioned,” said Mayor Wagner.

Pennings, also reminded me that while the festival is about music, it’s also about giving back. As such, a portion of proceeds will benefit Operation Song, a 501(c)(3) dedicated to helping veterans, active-duty service members,and their families tell their stories through songwriting. The organization will take center stage on Friday, October 10, leading the headlining round and reminding audiences of the powerful connection between music and healing.

With free harbor performances, ticketed headliner shows and one of the most stunning destinations in the South, the inaugural Destin Songwriter Festival promises a weekend that pairs perfectly with a cold drink, good company and great stories set to music.

Music lovers can visit www.destinsongwriterfestival.com for the latest updates, ticket information, artist announcements and insider travel tips for making the most of your festival fun.

Will Estell is a writer, editor, and media entrepreneur with more than 750 published articles in regional and national magazines covering tourism, real estate, automobiles, golf, food, music, and celebrity cover-story interviews. As chief creative officer of Estell Hussey Media LLC, he has helped launch 12 magazine titles from concept to market and served as editor in chief for several others. His latest project—a men’s lifestyle magazine blending Esquire, GQ, fitness, outdoors and auto—debuts nationwide in 2026. A Mississippi native, Will is the father of three who now lives in Destin and Navarre Beach with his wife, WEAR ABC 3 news anchor Laura Hussey-Estell.