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By Christopher Manson

Rique Gwin, a/k/a Captain Billy Bowlegs LXX, is ready for the annual Billy Bowlegs Pirate Festival happening May 14-16 at the Fort Walton Beach Landing Park; but that’s not all he’s been up to this year.

Gwin’s role as Captain Billy goes beyond the festival. Being “Captain Billy” includes promoting tourism in the area, “advertising how wonderful Fort Walton Beach is,” he elaborates. Gwin and his Krewe travel from Bradenton on up to Minnesota, visiting lots of regional pirate festivals. Gwin anticipates around a hundred or so out-of-towners coming to the Emerald Coast in May, a mighty boost for the local economy.

Earlier this year, Gwin – as Billy, in full costume – visited Liza Jackson Preparatory School where he read pirate-themed stories to students and handed out beads. Gwin and his “Air Raiders Krewe” will team up with other Krewes in Tallahassee later this year, complete with parade float, to entertain special needs children.

 

Gwin was announced as this year’s Captain Billy at a coronation pageant held last June at Niceville’s Mattie Kelly Arts Center. The identities of Billy’s Queen (Debbie Fisher), First Mate and First Mistress, and Honor Guard were also revealed. Gwin’s involvement with the Krewe dates back 15 years.

This year’s festival includes fireworks and live entertainment – the latter in partnership with the City of Fort Walton Beach’s much-loved Concerts on the Landing series – along with lots of vendors. The “skirmish” happens Friday night, after which, Gwin says, laughing, “I’ll end up in handcuffs.”

Spoiler alert: Captain Billy will be back at the festival site Saturday night to officially storm the city of Fort Walton Beach.

The festival is free to attend and attracted roughly 1,000 visitors last year. Gwin says the event was moved back to May from June after Covid, and thanks to that change, “crowds have started to grow again.”

The Billy Bowlegs Parade, set for Monday, May 18, along Eglin Parkway, is a popular Greater Fort Walton Beach Chamber of Commerce event that Gwin and his Krewe support and happily participate in.

Prior to Billy Bowlegs Festival 2026, a Downtown Fort Walton Beach pub crawl is scheduled for Friday, May 8. Ben Merrell and Soundside Bar are hosting.

On Thursday, May 14, the Little Pirates Scavenger Hunt will be held in Downtown FWB. The Krewe will meet the kids on the side street by Parlour Doughnuts and then the children will proceed through Downtown FWB. Gwin encourages Destin Life readers to listen to the local Cumulus radio stations and visit the Billy Bowlegs Pirate Festival Facebook page starting in April to unearth “clues” concerning the Bowlegs coin hunt. The grand prize winner will be announced at the festival Saturday evening.

Gwin wishes to recognize Felicity Plastic Surgery, this year’s presenting sponsor, whose event-worthy tagline is “Pursue YOUR happiness.” Learn more at felicityplasticsurgery.com. The festival benefits the William Augustus Bowles Historical Foundation, a 501(c)(3) organization that promotes a love for local history.

Vendor applications are available on the Billy Bowlegs Pirate Festival Facebook page.

“The city is really supportive,” adds Gwin, noting that all of the construction around the Landing is expected to be completed in time for the big event. “Last year was a little challenging with all the traffic barricades.”

Discover more at kreweofbowlegs.com.

The Bowlegs 70 Krewe

Captain Billy LXX – Rique Gwin
Captain’s Co-pilot – Kelly Gwin
Queen of Bowlegs – Debbie Fisher
Queen’s Navigator – J. Mark Fisher
First Mate – Mark Grindland
First Mistress – Mollie Grindland

The Honor Guard – Schuyler and Taylor Black, Michael and Erin Goodosn, Joe and Morgan Zwickel, Scott Flint and Nancy Kline, Mike and Kelly Bedsole, Tyler and Casey Murray, Chris and Heather Thomas, William Goolsby and Elizabeth Sager, John and Keri Holguin, Matthew and Katie Jaquet.

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