In Preservation of Piracy

Billy Bowlegs Festival keeps local lore alive, bringing Florida pirate culture to Panhandle shores

Like many locals who grew up in and around Fort Walton Beach, the Billy Bowlegs festival is ingrained in my childhood memories.

I can recall the awe I experienced as pirates stormed The Landing, the excitement of hunting for treasure, the pure joy of being the one to help solve the clues that led to my very own gold coin, and the shock when the mayor was finally taken over by Bowlegs and his Krewe. 

Season 69’s Captain Billy Bowlegs, Michael Castleberry, says those experiences are what keep Bowlegs alive. 

“If we weren’t around, think about the kids going forward that would never have what you have,” he says. “We’re the only ones doing it. And we’re only doing it for people like you to have memories.”

The 2025 Billy Bowlegs Festival will take place from May 16-19, marking 70 years—the season being off by one year due to the COVID-19 pandemic—of Fort Walton Beach’s signature event. 

Historically, Bowlegs has been organized by the Greater Fort Walton Beach Chamber of Commerce in collaboration with the Krewe of Bowlegs. Today, that responsibility falls solely to the Krewe.

“We bring in all the vendors, all the booths, all the musicians—we now are in charge of the entire festival,” Castleberry says. “There’s a historic part of this event, and we don’t want to see it die.”

Under the Krewe’s leadership in 2024, Castleberry says the vendor enlistment was the largest they’ve ever had. 

“If you’re going to leave it up to us, we’re going to make it a party, and we’re going to make it a great event,” Castleberry says. 

“We just care about it so much,” says Season 69’s queen Zabrina Horne.

The Krewe is made up of about 175 active members. The season’s main Krewe is made up of the Top Six—the captain and his lackey (or significant other), the queen and her lackey, first mate, and first mistress. The Honor Guard—made up of 10 couples—appear as the second line of defense during the skirmish skits. 

The Top Six and Honor Guard members are selected during the previous season and kept secret until their reign begins. A season’s reign starts with coronation in June each year and ends with the festival weekend in May. 

“Everything has to be a complete secret,” Castleberry says.   

The 2026 season 70 royal court is currently in secret and will be revealed at the June coronation ceremony following the close out of season 69 in May. 

“Basically, we’re big fat liars for eight months when we can’t say anything to anybody,” jokes Horne. “That’s the fun of it I think, the mystery of it. Everyone’s trying to figure out who the new queen is and who the new captain is.”

After coronation, the Top Six and Honor Guard begin their season of community outreach, event appearances, and planning and preparation for their season. Too, the Krewe travels to and attends 13 parades throughout the year in communities across the state. 

“We dress up in our costumes, and we go to their ball representing Bowlegs at their festivity,” Castleberry says. “And then they come to town for our weekend, and they participate in our festivities and Bowlegs event.”

At home, formal balls help raise funds for nonprofits and charitable organizations, and the Krewe works with the Greater Fort Walton Beach Chamber of Commerce and makes time for school visits to interact with local kids. 

“Every year, the queen gets to choose a charity,” says current queen Horne, who selected One Hopeful Place as a Season 69 beneficiary. 

During the festival, cosplay is part of the culture for all ages, with attendees dressed in everything from traditional pirate attire to steampunk-inspired gear to renaissance-style costumes. 

“The kids are dressed, the adults are dressed, and they go to the nines with their pirate costumes,” Horne says. “It is really cool to see people really get into it. That brings everybody together.”

“Who doesn’t love a pirate?” says Castleberry. “That’s your future by creating that folklore.”

“And it’s fun to dress up,” adds Horne. 

The Krewe’s own cosplay helps bring the festival’s folklore to life, starting with the Friday night Storming of the City. The Top Six and Honor Guard perform a skirmish, battling against Fort Walton Beach in attempts to overtake the city. The mayor and volunteer military members act out the opposing side. 

“The mayor and his militia take us over—they will actually put me in a police car—and they win,” says Castleberry. “Then, Billy Bowlegs says, ‘I will be back.’” 

Come Saturday, Bowlegs keeps his promise, returning with the full 175-member Krewe to capture the mayor and celebrate with the full-day festival at The Landing.

“We want to keep it alive, keep it going the same way,” says Castleberry. “It’s the commitment to the city and the kids. When you show up and we’re dressed as pirates and queens, and the kids are going crazy, that’s really cool stuff.”

All efforts remain a testament to the Krewe’s preservation of piracy.