It’s Bowlegs Time!

Photos courtesy of Greater Fort Walton Beach Chamber of Commerce.

By Samantha Lambert


This month, pirates run amok in the city of Fort Walton Beach for the annual three-day tradition known as the Billy Bowlegs Pirate Festival. The festival has taken place every year since 1955, and this year’s festivities kick off the summer starting Friday, June 2. The Billy Bowlegs Torchlight Parade is Monday, June 5.


The origins of the Billy Bowlegs Festival date back to 1953, when the Fort Walton Beach Recreation Department created a water-ski show to give local residents and tourists something to enjoy over the Labor Day weekend. The show was held in Cinco Bayou and was a big hit with those in attendance. The next year, the event was handed to over to the local Jaycees who were in their first year of existence.


The 1954 event included a ski show, parade, fish fry, and dance at the community center. In 1955, the Jaycees had the idea of a festival based on the Gasparilla Festival in Tampa, the largest and oldest pirate festival in Florida. The Jaycees decided the festival would center on a pirate theme.


They chose the notorious and legendary William Augustus Bowles as their patron pirate. Bowles’ nickname was Captain Billy Bowlegs, and he was a pirate of controversial authenticity whose alleged dastardly deeds were widespread throughout the waters.


Members of the Jaycees grew beards and wore costumes made for the invasion of the city by Bowlegs and his pirate crew. On Labor Day that year, the pirates landed at the Fort Walton Beach Yacht Club to the delight of thousands of locals and visitors alike.


Also in 1955, a Krewe of Bowlegs was created based on the idea of the Krewe of Mardi Gras in Mobile. This group created a charter and decided to be ambassadors to promote Fort Walton Beach around the country. The Krewe of Bowlegs served as the only official ambassadors/tourist promoters for Fort Walton Beach until the Tourist Development Council was started in 1990.


The Jaycees, together with a small group of merchants, also decided to choose from their membership a Captain Billy Bowlegs as the reigning pirate of the three-day festival. The first Captain Billy was downtown retail merchant Nathan Fleet, who played the role so well that he was asked to do it again in 1956.


In 1968, the Greater Fort Walton Beach Chamber of Commerce took over the organization of the Billy Bowlegs Festival. The festival was then changed from an end of summer event to a kickoff of summer celebration the first weekend in June. Over the years, many activities have been added to the festival, including treasure hunts for both children and adults, fireworks, and a bigger, more elaborate pirate landing where the Mayor of Fort Walton Beach attempts to defend the city.


Former Mayor Mike Anderson was defeated by Captain Billy every year he was in office. Anderson tried everything to beat the pirates, enlisting the help of the Fort Walton Beach Police Department, military units from Eglin, and local children. But it was to no avail.


And how will the new mayor deal with Bowlegs and his Krewe? “I cannot reveal my ‘big’ plan in advance, lest that dastardly pirate Captain Bowlegs get wind of it,” says Dick Rynearson. “I will say, however, that as a former bomber pilot and weapons test engineer, I do have a ‘big’ plan, and the city will not go down easily.”


Captain Billy Bowlegs and his Krewe arrive at the Fort Walton Beach Landing Friday evening. The city will be “captured” and the Jolly Roger raised to signify the surrender of the city. It’s fun for the entire family and has become one of the top 10 pirate festivals in Florida.

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