Historic Picture


The Billy Bowlegs Festival started as a Labor Day water ski show and has turned into one of the nation’s longest-running and most popular pirate festivals. In 1953 some enterprising young business leaders, the Fort Walton Beach Jaycees, set out to create a fun festival that would bring tourist to "The Playground Area." They decided on a high-spirited, raucous pirate theme and they unanimously chose the notorious William Augustus Bowles as the patron pirate. The legend of Bowles, and his dastardly deeds, were widespread along the Emerald Coast.

The ski show quickly grew to a three-day festival. In 1955, Nathan Fleet, a downtown Fort Walton Beach retail merchant, was chosen as the first Captain Billy Bowlegs. Nathan reigned over the Festival and lead the pirate “raids," and so began the Krewe of Bowlegs. The overwhelming success of the celebration sparked enthusiasm throughout the Fort Walton Beach business community and a secret delegation of four was given the task of choosing the Billy Bowlegs each year from the Krewe of Bowlegs member list. The original 1957 Bowlegs Festival souvenir program lists the original Krewe membership as 75 men. They kept the identity of Billy Bowlegs secret until the unmasking ceremonies took place on the evening of the grand ball.

The festival was soon extended to a week long celebration and many events were added. Treasure hunts, fireworks displays, athletic events, A landing that includes a battle for the City of Fort Walton Beach and the hoisting of the Jolly Roger, and the Torchlight Parade are just some of the fun activities that the city residents and guests have enjoyed throughout the years.

Today, many Bowlegs members are second, and some are third, generation pirates. They carry on the tradition set forth by their pirate fathers. As indicated by the Constitution & Bylaws, Krewe membership is limited to 170, plus the former Captains and honorary members. The Society of Bowlegs, affectionately known as the SOBs, limits membership to those who have served the Krewe as Captain Billy. A new Captain Billy is selected each year from the Krewe membership by secret ballot. The past seven captains are solely responsible for the secret nominations and the current Captain selects the new Captain from those nominations. Once the new Billy is selected, he chooses his Queen, First Mate & Mistress, ten Honor Guard couples and the Children of the Court. The late Docie Bass, Captain Billy Bowlegs IV, was the first to select his Queen from the wives of the Krewe membership. Prior to that, the Queens were “captive wenches” and beauty contest winners. Krewe member’s children and grandchildren, that are high school seniors during the year, represent the Krewe as Princesses and Privateers. The identities of the entire court are kept secret until the elaborate Coronation Pageant.

Krewe members and their wives (the wenches) spend many hours designing and creating float, stage, and ball decorations each year that celebrate the colors, theme, and emblem that is selected by the Billy. Elaborate costumes are custom made for each member of the court in the selected colors. The costumes are worn throughout the year as the court represents the Krewe in the local community and as they travel as ambassadors to other cities to participate in festivals and parades. The Krewe enjoys camaraderie with other crews along the Gulf Coast and as far away as St. Paul, Minnesota where they participate in the Winter Carnival.

Hosted by the Greater Fort Walton Beach Chamber of Commerce and its annual sponsors, The Billy Bowlegs Pirate Festival is celebrated the first full weekend in June each year. The festival begins on Friday afternoon and in the evening Captain Billy, his Queen, First Mate and First Mistress, and the Honor Guard of ten couples sail to the Landing under a white flag and try to negotiate the surrender of the city with the Mayor. A Skirmish takes place between the pirates and the city militia. Captain Billy and his Krewe will depart vowing to return to take the city by force, and the city will celebrate their short lived victory with a huge display of fireworks. The festival continues on Saturday when Captain Billy and his Krewe of over 300 pirates and wenches launch a full-scale invasion to take the city from the Mayor and his Militia. The Krewe will share their loot, by tossing beads and coins to the crowds that come out to join in the festivities. On Monday, the city residents and guests will line-up on Eglin Parkway for the Torchlight Parade. The Krewe will toss the loot to the crowds and Captain Billy will celebrate his victory.

The Coronation Pageant, held at the Mattie Kelly Arts Center the following Saturday, is open to the public. The new Captain Billy, his queen, First Mate and First Mistress, ten Honor Guard couples, and Children of the Court will all be unmasked. The new Princesses and Privateers will also be introduced. Following the pageant, The new Captain Billy will host a private ball for Krewe members and honored guest to celebrate the end of the festival and a new year for the Krewe of Bowlegs.

Krewe of Bowlegs
PO Box 1077
Fort Walton Beach, FL 32549-1077