Fort Walton Beach wrapped up this year’s Billy Bowlegs Pirate Festival on Monday with its Torchlight Parade, closing out a 70-year tradition of pirate pageantry, mock battles, treasure lore, and civic celebration.
The festival is real enough. The pirate is harder to pin down.
At the Buccaneer Gift Shop on Miracle Strip Parkway, the story starts with a sidewalk sign that reads, “Pirate Booty Sold Here.” Inside, Cheryl Ring pointed toward a display near the entrance.
“We have pirate rubber duckies over in that little area there with the pirate stuff,” Ring said. “We have pirate t-shirts, pirate magnets, pirate key chains.”
Ring was wearing a pirate hat and an eye patch. The shop has been in her family since the 1970s, and her brother, Jeff Ring, said Billy Bowlegs has long been part of downtown Fort Walton Beach’s rhythm.
“It’s always been a fun thing you know, look for treasures,” he said. “They have the cannon crew and I guess it’s going on 70 years this year if I remember correctly.”
The cannon crew is part of the festival’s central bit of theater: the pirate landing, when Captain Billy Bowlegs and his krewe stage a mock takeover of the city, resisted by the mayor and his militia. This year’s landing was Saturday.
Mike Thomin knows the festival from the inside. He grew up in Mary Esther, searched for festival treasure as a child and later served as gun captain for the city militia during the mock pirate invasion.
That is to say: He's no carpet-bagging landlubber. He is, however, a historian.
“Billy Bowlegs, the character that the festival celebrates, was actually, basically just fictionalized,” Thomin said.
Thomin is director of education and interpretation for the Florida Public Archaeology Network and a senior faculty research associate at the University of West Florida. He has researched the festival’s origins and found a story less like a straight line than a tangle of folklore, tourism, and historical retrofitting.
The festival itself did not begin as a pirate commemoration.
“Originally the festival actually started as a water skiing event that the city of Fort Walton Beach hosted every year starting in 1953,” Thomin said.
By 1955, the pirate theme had taken hold, inspired in part by other Florida civic pageants, including Tampa’s Gasparilla Pirate Festival and Pensacola’s Fiesta of Five Flags.
The story local organizers used did not come from a ship’s log or maritime court record. Thomin said the earliest known version appeared in a 1930 treasure book.
In that story, a man named William Rogers leaves plantation life, joins Jean Lafitte’s circle, then settles around Santa Rosa Sound and Choctawhatchee Bay as the pirate Billy Bowlegs. He leaves behind a sunken schooner and buried treasure.
“That’s really the first publication we have of this particular story,” Thomin said.
That legend eventually became attached to Jesse Rogers, a real Mary Esther cattle rancher. The connection created a problem for Rogers’ descendants.
“People who were hunting for this treasure that they thought was really real actually started going into that cemetery and trying to dig his body up, which is of course really upset his family who still lived in the area,” Thomin said.
By the mid-1960s, festival leaders needed a different pirate — one less likely to send treasure hunters into a local family’s cemetery.
“They needed someone that they could legitimately say was a real individual who had connections to the Panhandle who was involved in piracy,” Thomin said.
They turned to William Augustus Bowles, a real figure from the Gulf Coast’s colonial era. But Thomin said there is no documentation Bowles was known as Billy Bowlegs by his contemporaries. His later maritime activity was centered farther east, around the St. Marks and Wakulla rivers, not Fort Walton Beach.
One festival organizer later explained the choice in a 1970s letter.
“It would add historic heritage to the character of the festival,” Thomin said, quoting the letter. “We felt that the flourish of Bowles’ signature could be interpreted as Bowlegs and legend could become fact.”
In other words, the connection was not discovered so much as made.
Of course, the real Bowles hardly needed embellishment. Born in Maryland, he came to Pensacola as a teenage Loyalist during the American Revolution. He later married into an influential Muscogee Creek family, challenged the powerful Pensacola trading firm Panton, Leslie & Co., issued privateering commissions and declared himself director general of the Creek Nation.
Privateers were not exactly pirates. They were private ship captains authorized to attack enemy vessels — in Bowles’ case, by a government he was trying to create.
Bowles’ story ended far from Fort Walton Beach. He was captured by Spanish authorities and died in prison in Cuba.
Still, the festival built around Billy Bowlegs, or at least the idea of him, has endured.
On Monday night, families lined Eglin Parkway as pirate ship floats rolled past in the Torchlight Parade. Kids held bags for candy and beads.
John Timmerman was among them. He wore a red do-rag, an eye patch and a stuffed parrot named Peggy perched on his shoulder. His son was dressed to match, and the two passed the time fighting with foam swords.
The Timmermans are from Clemson, South Carolina. They stumbled onto the parade during a beach trip a few years ago.
“About four years ago, we discovered this and it’s just kind of become a tradition over the past four years," Timmerman said. "We get more piratey things every time we come, and we just keep coming."
That may be the clearest way to understand Billy Bowlegs now: The pirate might have many faces. The buried treasure may belong more to legend than fact. But after seven decades, Billy Bowlegs has become part of Fort Walton Beach history in another way: as a tradition the community keeps performing, year after year.
