A $20 Seat to Grammy-Winning Talent

by Kerri Parker

In a town known for its quiet charm and historic beauty, Friday nights in DeFuniak Springs are becoming something unexpected: electric. Once a month, the lights come up on the stage of the Chautauqua Theater, and the energy inside feels more like a night in Nashville, Austin, or New Orleans than small-town Florida.

At the heart of it all is Tim Jackson’s Storytellers Tour—a concert series that brings Grammy-winning and Grammy-nominated artists to Walton County, offering an up-close, deeply personal performance that you can’t stream, fake, or forget. The series was created by Tim Jackson, a celebrated singer-songwriter and producer with a gift for discovering talent and drawing the best out of them. These artists don’t just sing—they tell the stories behind the music. It’s unscripted, raw, and often unforgettable.

The format is intimate by design: one night, one stage, one story at a time. These aren’t your typical tour stops. There are no backup dancers, no pyrotechnics. Just world-class musicians, a stage that’s stood for over a century, and an audience close enough to catch the emotion behind every lyric.

And here’s the best part: tickets are just $20.

To put that in perspective: about the same cost as one overpriced candle you don’t even light—and you’re getting a front-row seat (literally, if you want it) to an evening of music that often sells out in major venues for ten times the price.

Each show begins at 7 PM, which leaves the perfect window to enjoy dinner before curtain time. Just a short walk from the theater, you’ll find several local favorites ready to kick off your evening. Iron & Grape Italian Kitchen offers Chef Todd Misener’s seasonal, chef-inspired menu—handmade pastas, garden-fresh ingredients, and scratch-made dishes that set the tone for an unforgettable night. For something heartier and full of Southern charm, Sweet Southern Comfort serves up classic comfort food done right, while Café Nola brings New Orleans flavor to the table with its Cajun and Creole favorites. And if you’re craving something a little different, our nearby V Pho Vietnamese restaurant offers fresh, flavorful options that make for a delicious start before the show.

The next installment of the Storytellers Tour takes place Friday, October 24. Expect the unexpected—whether it’s a surprise guest joining on stage, a soulful ballad you’ve never heard before, or a familiar hit performed in a way that feels brand new. But don’t expect tickets to last.

This is more than just a concert. It’s a cultural moment that’s quietly redefining Friday nights in Walton County. And the secret is starting to get out.

HWY 331 PRO Tip: We suggest purchasing tickets in advance, https://fl-chautauqua.square.site/s/shop.

Make a Night of It—Or a Weekend

If you really want to slow down and savor the experience, consider booking a room at the Sunbright Inn, a beautifully restored Victorian home just a hop, skip, and a jump from the Chautauqua Theater. With its wraparound porches, spacious rooms, and Southern charm, the inn feels like stepping into a living postcard. After the show, you’re just steps away from your room—and in the morning, you’ll wake to one of the most authentic farmers markets in Northwest Florida.

Just around the corner on Baldwin Avenue, Main Street DeFuniak Springs’ Farmers Market runs every Saturday from 8 AM to 1 PM, offering everything from just-picked produce to small-batch baked goods, handmade wares, and live local music. It’s a perfect blend of culture, community, and craft—and a beautiful reminder that sometimes, the best weekend getaways are the ones closest to home.

Circle Back to DeFuniak

Locals often say there is something magical about Lake DeFuniak — a rare, perfectly round, spring-fed lake whose natural beauty has drawn people to its shores for generations. It is a place that inspires reflection, connection, and a return to its quiet majesty time and again. Join a fitness group that meets every Saturday morning to walk, jog, bike or paddle around Lake DeFuniak. It is free and open to the public. Folks meet up behind the Hall of Brotherhood at 9 AM and promptly get moving! Learn more here.