Billy Bowlegs Pirate Festival

(This following information is taken from a Coronation Program for the Krewe of Bowlegs on June 5, 1982)

The Billy Bowlegs Festival grew out of a Labor Day ski show celebration back in 1953, which was the brainchild of some enterprising young businessmen, the JAYCEES, eager to latch onto a project that would warrant their time and efforts, be fun, and bring more tourists into the area. The idea of a Gasparilla-type observance centered on a “pirate” theme, and they unanimously chose as their patron pirate the notorious and legendary William Augustus Bowles, a pirate of controversial authenticity whose alleged dastardly deeds were widespread throughout the area. Nathan Fleet, a downtown Fort Walton Beach retail merchant at that time, was chosen as the first Captain Billy Bowlegs to reign over the Festival and lead the pirate “raids.” (In later years, his son, Judge Erwin Fleet, reigned as Cap’n Billy XIV.) The overwhelming success and acceptance of the initial celebration sparked great enthusiasm and interest among other businessmen of the community. A small group of merchants, of which two, together with two from the JAYCEES, were secretly delegated to choose from the member list the Billy Bowlegs as reigning pirate of the three-day festival, his identity to remain unknown until the unmasking ceremonies took place on the evening of the grant ball. Due to the huge success of the festival, events were added such as treasure hunts for children, parades, gigantic fireworks displays, athletic events, a landing to include the townspeople with the “capture” of the City and the hoisting of the Jolly Roger to signify the total surrender of the City. Beards were grown, costumes made, and over the years became more elaborate. Professional floats were added to the Grand Torchlight Parade and a glittering Coronation Pageant, open to the public, at which a new Cap’n Billy, his queen, a first mate and his lady, ten honor guard couples and children of the court are unmasked each year, with a private ball and midnight breakfast for Krewe members and honored guests climaxing the now week-long festival. Thus a tradition was born: The Billy Bowlegs Festival, with the infamous Krewe of Bowlegs and its current Cap’n as the “Star” of the show.

The annual Billy Bowlegs Pirate Festival is held in Fort Walton Beach, Florida. The festival honors the local pirate legend, and is unrelated to the Seminole chief Billy Bowlegs. Similar to Mardi Gras, the festival consists of a parade, fireworks, and associated celebrations.

The festival originated in the 1950s as a boat and water skiing show. Contrary to popular belief, there is no period documentation supporting claims that William Augustus Bowles was named "Billy Bowlegs" (nor is there any evidence Bowles even set foot near what is today Fort Walton). The confusion over the names seems to stem from the similarity of the name "William Bowles" and "Billy Bowlegs", the Seminole Chief who warred with the United States during the Seminole Wars. Billy Bowlegs was born five years after Bowles' death, though both did live and fight in Florida. Coupled with that is the fact that William Bowles bore the British Army rank of Ensign as a young man, which confuses many modern Americans as the rank is also a modern, naval rank.

The festival has a Mardi Gras flair rather than a historical focus, with locals dressing up in cocked hats (such headgear was not in fashion when Bowles was active in the late 1790s to early 19th century from his base near Apalachicola).