The 68th Billy Bowlegs Pirate Festival begins in Fort Walton Beach. Here's what to know

For 67 years, Captain Billy Bowlegs and his krewe have descended upon Fort Walton Beach for a weekend filled with debauchery, revelry and good times with the residents of Fort Walton Beach.

This weekend, for the 68th time, Captain Billy, his pirate queen and his merry band of miscreants look to invade the city, much to the chagrin of Fort Walton Beach Mayor Dick Rynearson.

Here is everything you need to know about the annual pirate festival.

Festival History

Whether you just moved into town, are a tourist here for the weekend or are a reporter for the Northwest Florida Daily News experiencing the festival for the first time, we would like to get you up to speed on what makes the annual pirate festival a hit with locals.

It all started in 1953, when a group of business leaders called the Fort Walton Beach Jaycees, short for junior members of The Greater Fort Walton Beach Chamber of Commerce, wanted to create a family-friendly event that would attract tourists from far and wide to the "Playground of the Emerald Coast."

The festival takes inspiration from Mardi Gras celebrations in Mobile, Alabama, and the Gasparilla Pirate Festival in Tampa. Ted Corcoran, Fort Walton Beach Chamber of Commerce president, said the Labor Day water ski show, which was held for around three years prior, turned into a three-day festival that we now know as "The Billy Bowlegs Pirate Festival" in 1955.

Nathan Fleet, a downtown Fort Walton Beach business owner, was selected as the first Captain Billy Bowlegs and led the first pirate raid against the city. Since then, a new "Billy" has been chosen each year. Bill Kilpatrick will lead the invasion for the 68th Billy Bowlegs Pirate Festival, with Pirate Queen Sharen Burt along his side.

Until recently, the event was usually held in June. But after the festival was canceled for the first time in 2020 because of the COVID-19 pandemic, it returned to a new date held in May. The event can now be seen as a "kickoff party" to the summer season in Fort Walton Beach.

Who is Billy Bowlegs?

The Billy Bowlegs Pirate Festival celebrates a figure who holds a significant place in Seminole history, yet much of the festival's portrayal is misaligned with the real Billy Bowlegs. Contrary to popular belief, Billy Bowlegs wasn't an individual person — rather, the name of three Seminole chiefs who spent no time in Northwest Florida.

According to the Krewe of Bowlegs website, William Augusts Bowles was born into a wealthy Maryland Tory family in 1763 and began his military career with the British Army during the American Revolution when he was 13.

By December 1778, Bowles first appeared in Northwest Florida when he landed in Pensacola but missed the return boat to his ship. Once he returned, he was dismissed from service for dereliction of duty without a trial. Stuck in Pensacola, Bowles joined the Creek tribes and frequented various areas in our area.

After integrating with other tribes in Florida, like the Seminoles and Cherokee, Bowles traveled to Nova Scotia, England, and the Bahamas to garner support for creating a free state for Native Americans in the southeastern United States. Despite setbacks and imprisonments, Bowles declared war against Spain and the United States in his pursuit of sovereignty.

This led to a breaking point in 1803 when Bowles was captured and imprisoned by Benjamin Hawkins, an Indian agent and future senator from North Carolina. Hawkins orchestrated his arrest during a conference at Tukabatchee, one of the four "mother towns" of the Muscogee Creek Confederacy, after Bowles proclaimed himself as "king of all the Indian nations."

Bowles was handed over to Spanish authorities and imprisoned in Morro Castle prison in Havana, Cuba, where he later died in 1805.

His biography on the website claims that Bowles and the State of Muskogee were the catalyst for the removal of the Seminole tribe from Florida and led to the First Seminole War, which the U.S. Naval Historical Center says began in 1816.

Timeline of events

Below is the schedule of events for the 68th annual Billy Bowlegs Pirate Festival in Fort Walton Beach. According to event organizers on Facebook, "a pirate never let a little rain get in the way of a great time."

According to a forecast released by the National Weather Service in Mobile, the Northwest Florida Daily News coverage area is expected to get 4-plus inches of rain through the weekend.

Thursday, May 16

A pre-invasion meet and greet will occur from 4 to 6 p.m. between Burrito del Sol and Parlor Doughnuts on Ferry Road SE. The day's festivities will include a Little Scallywags Pirate Walk, held simultaneously on Miracle Strip Parkway, where kids can gain loot and treasures from local businesses.

Friday, May 17

Day two of the 68th annual Billy Bowlegs Pirate Festival will coincide with Concerts at the Landing, with a performance by The Midnight Shepherds at 6 p.m.

At 7 p.m., Captian Bowlegs and his merry krewe are expected to observe the city defenses before his arrival on Saturday. Because of this, Mayor Dick Rynearson has called for the arrest of Capitan Billy Bowlegs and asked for the U.S. Army's 6th Ranger Battalion to aid the Fort Walton Beach Police Department in defending Fort Walton Beach.

Following the skirmish, fireworks will signal the end of the day's festivities at 8:45 p.m.

Saturday, May 17

As Rynearson licks his wounds after Captain Billy escapes from jail, residents and tourists can enjoy local vendors and food trucks at 10 a.m. at The Landing. From 11:30 a.m. to 3:15 p.m., Meg Phillips and Mile Zero will provide live music at The Landing's main stage.

About 3:30 p.m., Capitan Bowlegs will announce his arrival by cannon fire as his ship passes beneath the Brooks Bridge as his merry band makes their way to The Landing, where the mayor will succumb to Captain Billy's regalia. From there, a pirate celebration will continue into the evening, with Bradley Gaskin's performance at 5 p.m. at The Landing stage.

Monday, May 20

As a final showing of defiance toward the mayor, a torchlight parade will end Captain Billy's weekend-long reign as they celebrate another successful capture of Fort Walton Beach.

The festivities begin at 7 p.m., when Captain Billy and his Krewe of Bowlegs will travel up Eglin Parkway, between Ferry Avenue and Hughes Street, tossing beads and small prizes that represent the treasures found by the pirates in their annual takeover.

This article originally appeared on Northwest Florida Daily News: Billy Bowlegs Pirate Festival: Invading Fort Walton Beach since 1955