The History of the Billy Bowlegs Pirate Festival

It started out as a water skiing festival in 1953, and has turned into one of the nation’s longest-running and most popular pirate festivals. Sponsored by the Greater Fort Walton Beach Chamber of Commerce and its annual sponsors, the Billy Bowlegs Pirate Festival always takes place on the first full weekend in June. People come by land, sea, and air to join in this family-friendly event.

The first pirate sightings will undoubtedly be at the Thursday night festivities at the landing. Those bold pirates will be scouting out the town, looking for the Mayor's weaknesses - and tempting the locals into debaucherous behavior! Capt. Billy LX has decided to come to town early this year - with his Krewe of Bowlegs and other Krewes from around the nation. We've heard talk of a band and more entertainment - something to distract the locals. Stay tuned!

This year, there’ll be more pirates than ever! And yes, of course Capt. Billy and his Krewe will arrive by sea to “scout” the Landing on Friday, June 1, and return to implement their dastardly plans on Saturday, June 2.

Mayor Rynearson of Fort Walton Beach and Reed's Raiders are plotting and planning their defense of the City - will this be the year that the Mayor keeps control of Fort Walton Beach??? Or once again, will the Krewe of Bowlegs take over our fair city?

Regardless of who prevails, there'll be merriment, music, and fun as the Torchlight Parade returns to Monday night, June 4. Come down to Eglin Parkway (between 1st Street and Hughes) and enjoy the shenanigans!

(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.

pirate captain pirate ship cannon pirates female pirate pirates fireworks