By Christopher Manson
“Now and then we had the hope that if we lived and were good, God would permit us to be pirates.”
– Mark Twain, Life on the Mississippi
The Billy Bowlegs Pirate Festival returns to Fort Walton Beach May 15-19 with fireworks, a parade, fun family activities and much more. This is the 69th festival benefiting the William Augustus Bowles Historical Foundation, a 501(c)(3) organization that promotes a love for local history.
In 1955, Fort Walton Beach businessman Nathan Fleet reigned over the inaugural festival as Captain Billy Bowlegs. The successful event led to the current multi-day festival that takes place at the Landing Park. Around 5,000 pirates and landlubbers are expected to attend this year.
Captain Billy Bowlegs LXIX Michael Castleberry has called Fort Walton Beach home since 1998. He will be joined by Pirate Queen Zabrina Horne, along with First Mate and Mistress Matt and Kacy Turpin.
High school students from Niceville, Destin, Choctawhatchee and Fort Walton Beach will serve as Princesses and Privateers. The Honor Guard LXIX consists of Shane and Jessica Atkinson, Ben and Jaris Buehler, Creed and Elizabeth Burkhart, David and Remi Densmore, Scott and Regina Groundwater, Larry and Donita Messinger, Joe and Tammy O’Gallagher, Matt and Becky Scaringe, John and Channa Schuster, and Michael Voit and Angela Hassell, all of whom look forward to representing the Krewe.
The Krewe of Bowlegs was founded in 1954 with the goal of attracting tourists to the area. Today, the Krewe provides invaluable service beyond the annual festival. According to the Krewe’s website, you can find them “wherever a daring, adventurous swashbuckler (or just a guy in a funny pirate hat) is needed.”
2025 Events
The Bowlegs Treasure Hunt begins in April, with clues being announced on local radio. Participants can search for Bowlegs coins and win a piece of Captain Billy’s treasure. Look for updates at kreweofbowlegs.com, along with an irresistible poem.
On Thursday, May 15 at 4 p.m., Captain Billy and his Krewe arrive on Ferry Road for the Pre-Invasion. Children will be greeted, photos taken and treasure given away until 6 p.m.
The Skirmish at the Landing Park follows on Friday, May 16, at 8 p.m. An Arts and Crafts Festival is planned for 5 p.m., followed by a performance by blues rockers Thin Ice at 6 p.m. Captain Billy and his scouting party are expected to land at 7 p.m., and make sure you stick around for a spectacular fireworks show at 8:45 p.m.
Saturday, May 17, the much-anticipated pirate invasion takes place at the Landing Park with Captain Billy and his Krewe landing around 3:30 p.m. Arts and crafts begin at 10 a.m., followed by live music from The Friskeys from 1 to 3 p.m. The celebration continues until 7 p.m.
The band Duchess kicks off its first Bowlegs gig at 4 p.m. Duchess has performed at numerous Krewe of Bowlegs parties, as well as the Concert on the Landing series. Duchess’ Doug Bowers and Chuck Tidwell have played the festival before with the band 423. Bowers says festivalgoers can expect “high-energy Seventies and Eighties classic rock (from a) band that loves to interact with its audience.” Learn more at duchessband.com.
The 2025 festivities wrap up with the Torchlight Parade Monday, May 19, beginning at 7 p.m. The parade route begins at First Street and Eglin Parkway and rolls northward to Hughes Street, with sea-worthy floats, eye-popping floats and non-stop entertainment. For registration information and more, visit fwbchamber.org.
Videos of previous parades are widely available on a number of YouTube channels, notably Emerald Coast TV’s clip from the 2018 event which has attracted thousands of viewers.
This year’s presenting/title sponsor for the Billy Bowlegs Pirate Festival is Felicity Plastic Surgery, specifically noted reconstructive/plastic surgeon Dr. Liz Sager. “We would not be able to have this festival at all if we didn’t have her generous sponsorship,” says Festival Coordinator Cali Hlavac. Felicity’s slogan is, appropriately enough considering the Bowlegs Festival vibe, “Pursue your happiness.” Discover more at felicityplasticsurgery.com.
The tradition of Billy Bowlegs has spanned over 75 years and has become an important part of our local history,” says Hlavac. “From finding the hidden coins and the Friday fireworks to watching Captain Billy take over the Landing, there is something all ages can enjoy. We are looking forward to bringing the community together for another great year of festivities.”
