Some of my earliest memories are of celebrating Billy Bowlegs on the water on Okaloosa Island. My grandmother had a house on the Santa Rosa Sound and we would go to her house on the first full weekend in June and watch the reenacted battle between the mayor and Capt. Billy Bowlegs.

As I’ve gotten older, the Billy Bowlegs event has grown, and changed, and now it is the most sought-after boating event in the Destin-Ft Walton Beach area. We sell out for Billy Bowlegs every year months in advance, even before the July 4th or Memorial Day weekend reservations are full, so if you’re looking for a boat to rent for Billy Bowlegs, make sure to plan ahead!

What is the Billy Bowlegs Pirate Festival?

The Fort Walton Beach Chamber of Commerce began hosting a waterskiing festival in 1953. The waterskiing part didn’t last, but the chosen pirate theme took hold and became an annual tradition, and events were added over time to include a parade, treasure hunts, costume contests, and athletic events, all culminating with the arrival of Capt. Billy and his crew via pirate ship to the Ft Walton Beach Landing. There is a skirmish where the mayor and his crew try to “defend the city”. Cannons are fired and it’s all great fun on the water and on land.

billy bowlegs

The Krewe of Bowlegs approaching the city.

Who was Billy Bowlegs?

According to the Fort Walton Beach Chamber of Commerce, the patron “Billy Bowlegs” is a legendary pirate whose name was William Augustus Bowles, a “pirate of controversial authenticity whose alleged dastardly deeds were widespread throughout the area.” Personally, I think this story is the more “politically-correct” version, rumored to have been created after the real Billy Bowlegs’s grave was desecrated and complaints were received by his heirs. There was actually a pirate named Billy Bowlegs, according to my research

The real story of Billy Bowlegs actually goes something a little more like this:  Billy Bowlegs was named William “Billy Bowlegs” Rogers, a real pirate whose sunken ship was discovered and excavated in 1959 in the Northeast Choctawhatchee Bay. As the story goes, this Billy Bowlegs operated in the Gulf Coast for around 40 years. In 1840, he and his krewe were chased down by a British Warship. They were narrowly able to escape by entering a lagoon that was too shallow for the warship to enter, but were forced into hiding. They hid some of their treasure ashore, the rest stored in their pirate ship, then sunk their treasure-laden ship, and Billy Bowlegs left his crew to stand guard while he took off for New Orleans to bring back his family and diving equipment to retrieve the treasure.

Once he returned, however, most of the crew had fallen ill or had been attacked by Indians and the diving operation did not go well. Bowlegs’ wife soon took ill as well, and died, and it is said that Billy Bowlegs lost interest in retrieving his treasure. Instead, he sailed to the mainland and built a cabin where he spent his last days watching over the treasure. As all good pirate stories go, the treasure was never really found, but there have been reports of people finding gold and silver coins all along the Santa Rosa Island  area and the Choctawhatchee Bay.

If you ask me, that’s a story that’s a lot more fun to tell, politically correct, or not…

What to expect

Over the years two crowds have emerged: the family-oriented festival goers, and the wild and crazy “ne’er do wells”. The family crowd tends to watch from the shoreline. The party crowd gets out on the water and a lot of craziness ensues. Boats start making their way to the Santa Rosa Sound early in the morning, tie up together, and spend the day drinking and partying the day away. (Imagine Mardi Gras, but on the water.) Fun for adults? Sure! Would I take my kids on a boat to Billy Bowlegs? Not a chance. But I would take them to the festival down by the Landing, so if you are thinking about going to Billy Bowlegs with children, my advice is to go by land rather than by sea.

Billy Bowlegs Pirate Festival

Billy Bowlegs celebration on the water.

Schedule of Events

Whether you decide to celebrate by land or by sea, there will be plenty to do during the 3-day event.

The pirate festivities begin with the kids’ Pirate Walk (4 to 6 pm), costumed trick or treating hosted by the downtown merchants at their stores along Miracle Strip Parkway.   At The Landing, the Festival will actually begin at 6 pm, with food and craft vendors creating a Pirate’s Village at the waterfront park.  The Bowlegs Pub Crawl will also begin at 6.

The Torchlight Parade will wind its way up Eglin Parkway at 7 pm, with dozens of floats representing local businesses and clubs, visiting krewes, and Fort Walton Beach’s very own Krewe of Bowlegs.

Following the Parade, activities will move back to the Landing, where the theme for Thursday is “Pirate Zombie Night”.  There’ll be costume contests and pirate zombie fun, with prizes from AMC’s “Walking Dead,” provided by Cox. Tom Mason and the Blue Buccaneers will perform at 8 pm.

On Friday, the Festival will open at 3, and the popular Pirate Skirmish will begin at 7, followed by a “Talk Like a Pirate” contest and music by Cabo Rock.  There will be a 20-minute fireworks show at 9:30pm.

There’ll be pirate shenanigans all day on Saturday, from 10 am to 9 pm, in the park and of course the main event on the water takes place when Capt. Billy Bowlegs and his Krewe return for their ultimate standoff with Mayor Anderson and his militia at 4 pm on Saturday. Of course, the boats will have gathered long before that for a day of partying and fun.


If you’re interested in renting a boat for Billy Bowlegs, contact us to be added to our waiting list, or add it to your to-do list for next year and come see us then!


[photo credit: Flickr user @kyletsui]