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Pirates set to invade Fort Walton Beach for 69th Billy Bowlegs Festival

Captain Billy and his crew will sail into Fort Walton Beach for the four-day celebration featuring pirate skirmishes, music, fireworks and a parade.
Source: City of FWB

Pirates will once again storm the shores of Fort Walton Beach as the 69th Annual Billy Bowlegs Pirate Festival returns May 15-19.

  • The free community celebration spans four days across multiple downtown locations, featuring the traditional pirate invasion and takeover of the city.

“Captain Billy Bowlegs returns and comes ashore at Fort Walton Beach Landing with the entire Krewe of Bowlegs, as well as allies from visiting Krewes across the country,” festival organizers said.

The festivities begin Thursday, May 15, with the “Little Scallywags Pirate Walk” from 4-6 p.m. at the south end of Ferry Road SE near Highway 98. Captain Billy and his crew will arrive aboard the Blackhawk float to greet children, take photos and distribute treasure.

Friday brings the Pirate Skirmish from 5-9 p.m. at Fort Walton Beach Landing, where Captain Billy and scouts arrive by water to scout the city.

  • “The mayor of Fort Walton Beach and his forces are prepared and they’ve threatened to arrest Captain Billy if he lands, resulting in a skirmish,” explained festival organizers.

Vendor booths and food trucks open at 5 p.m. Friday, followed by City of Fort Walton Beach Concerts at the Landing at 6 p.m., the Pirate Skirmish at 6:30 p.m., and fireworks over Santa Rosa Sound at 8:30 p.m.

The main event – Saturday’s Pirate Invasion – runs from 10 a.m. to 6 p.m. at Fort Walton Beach Landing. Activities include vendor booths, food trucks, and live music from The Friskeys (1-3 p.m.) and Duchess (4-6 p.m.).

  • The highlight occurs at 3 p.m. when Captain Billy leads his full invasion. According to organizers, “The mayor will try everything to stop him but Captain Billy will prevail and take over the city of Fort Walton Beach again.”

The festival concludes Monday with the Torchlight Parade at 7 p.m., presented by Eglin Wealth Management and organized by the Greater Fort Walton Beach Chamber of Commerce. Captain Billy and the Krewe will travel aboard five floats along Eglin Parkway from First Street north to Hughes Street, “sharing their loot with those cheering them on.”

The Billy Bowlegs Pirate Festival is organized by the William Augustus Bowles Museum & Historical Foundation in partnership with the City of Fort Walton Beach, the Krewe of Bowlegs, and the Fort Walton Beach Chamber of Commerce.

For more information or a complete schedule, visit https://billybowlegsfestival.com/.

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“Maybe the Shalimar Mayor can use some of that speed trap money a have Eglin Pkwy Repaved.”
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Scott Schaeffler commented on WordroW: May 15, 2026
“3:16, 5 attempts”
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“no work had been done since February. I drive this road 4 days a week to and from work and fortunately I drive a truck. I feel for anybody driving...”
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Scott Schaeffler commented on WordroW: May 14, 2026
“5 attempts, 1:10”
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“Totally agree, the Destin harbor is bad enough already, they've already built all the new boat slips which take up navigable water. Another marina, more boats, less space and more...”
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“What they have started so far is terrible. Who paves in random 50-300 yard segments. That is not cost effective, nor a good management of time & resources. I am...”
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“Thank you Shalimar Mayor for pushing FDOT's button. We currently have a duopoly on major paving projects which needs to be broken”
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