Avast, ye Mateys! It’s time to open your treasure chest, dig out your eyepatch and sword, and get ready for the 66th Annual Billy Bowlegs Pirate Festival from May 12-16, 2022! You’ll find that iniquitous Billy Bowlegs with his pirates and their dastardly deeds off t’shores of t’Emerald Coast around Destin and Fort Walton Beach! Rumor has it that he be plannin’ to dock his ship yet again at the Fort Walton Beach Landing on the Gulf for this year’s festival. So, welcome landlubbers and swabbys of all ages t’dis jolly family event! Bowlegs’ll be drawin’ in some 500 “ships” expected for the main event on the waterfront as they “capture” the beach in his honor! Everyone’s a pirate at Bowlegs!

Annual Billy Bowlegs Pirate Festival

Did you know it all began as a water-skiing festival in 1953 with a real local pirate legend, William Augustus “Billy Bowlegs” Bowles? The Billy Bowlegs Festival now draws visitors from all over to experience this one-of-a-kind, pirate festival where ya can emjoy the day o’ frollickin’, skirmish, grub and grog Gar and all sorts of colorful pirate activity all over town—lots of hoopla complete with booty, treasure and fun!

Schedule of Events

This year, there’ll be more pirates than ever! And yay, of course Capt. Billy and his Krewe will arrive by sea to “scout” the Landing!

Thursday, May 12

A Downtown Pub Crawl will kick-off the festival from 6-9 p.m. Get a card at one of the participating bars and turn it in with all of your stamps by 9 p.m. for a chance to win great prizes. Stops include Coasters, The Block, Downtown Music Hall, Fokker’s Pub, Props Brewery and Salty Duck.

Friday, May 13

The Bowlegs Krewe is expected to attack the city sometime between 6-8 p.m. as the Hollywood Vagabonds perform live. We’ll see what tricks and strategies Mayor Dick Rynearson and the Reed’s Raiders will use to repel Capt. Billy’s invasion this year. Their invasion will be followed by a fireworks show at 8:30 p.m. Food and concessions will be available throughout the evening.

Saturday, May 14

A kid-friendly day of fun is planned from 11 a.m. to 3 p.m. at Fort Walton Beach Landing Park. They’ll have bounce houses, pirate-themed activities, face painting and food and concessions. Don’t miss the arrival of Captain Billy 66 at 2 p.m. as he prepares for another takeover of the city! He’ll be handing out booty, coins and stopping for photos along the way.

A block party will be held from 2-5 p.m. between Burrito Del Sol and the Salty Duck with a live DJ at the Blackhawk Pirate Ship and a special pirate guest.

Kids Pirate Zone

Monday, May 16

“Make way, mateys!” You’ll love the excitement of da Billy Bowlegs Torchlight Parade on Monday, May 16 at 7 p.m. Roughly 100 floats, boats, and vessels will wend their way from First Street up Eglin Parkway, and they’ll be lobbing beads and throws for you to catch and corral.

Condos Near the Billy Bowlegs Festival

Destin Vacation

Shiver me timbers! Be sure not t’ miss the Billy Bowlegs Festi’al Aye calling thousands of landlubbers in by land, sea and air. If yer wantin’ to chart your course to the 2019 Billy Bowlegs Festival, stay nearby in a Destin Florida condo, where ye can plan your treasure of a stay in an array of accommodations with Gulf views and convenient to all the hoopla and mischief.

Event Summary
66th Annual Billy Bowlegs Pirate Festival
Fort Walton Beach Landing Park, 139 Brooks St. SE,Fort Walton Beach,FL-32547
Start Date
May 12, 2022
End Date
May 16, 2022
Shiver me timbers! Be sure not t' miss the Billy Bowlegs Festival, calling thousands of landlubbers in by land, sea and air.