How to Enjoy the Annual Billy Bowlegs Pirate Festival & Fort Walton Beach
Blog written by: Tracy S.
Tracy writes for Seaspray Beach Vacation Rentals, sharing vacation planning tips, travel insights, local things to do, and property highlights to help guests make the most of their time along the Emerald Coast.
Argh! Welcome, mateys to a treasure trove of information about the 70th Annual Billy Bowlegs Pirate Festival and how to make the most of an exciting long weekend in Fort Walton Beach! Follow along on an epic adventure as we help you map out the perfect itinerary. Grab your pirate garb and be prepared to immerse yourself in a world of swashbuckling fun. Don’t miss your chance to meet Captain Billy Bowlegs and his Krewe, search for treasure, watch the fireworks, listen to live music, attend the pirate parade, and more.
In this article:
- Annaul Billy Bowlegs Pirate Festival Overview
- Pre-Invasion & Little Scallywags Pirate Walk
- Pirate Landing & Skirmish
- Pirate Invasion
- Torchlight Parade
- Treasure Hunt
- Finding a Vacation Rental Near the Pirate Festival
70th Annual Billy Bowlegs Pirate Festival
Dates: Thursday, May 14th – Monday, May 18th, 2026
Location: Fort Walton Beach, Florida
This iconic pirate festival is now in its 70th year. This family-friendly event is all about William Augustus Bowles (aka Billy Bowlegs), an infamous pirate who allegedly sailed the waters of the Gulf Coast, and his krewe. Held all along the picturesque Emerald Coast, this 5-day event has grown since its maiden voyage in 1956.
Join the pirate-themed celebrations by attending one or all of the festival happenings!
Festival Schedule & Happenings
Pre-Invasion & Little Scallywags Pirate Walk
Date: Thursday, May 14, 2026
Time: 5:00 PM
Location: Downtown Fort Walton Beach (South end of Ferry Road SE, near Hwy 98 and Burrito del Sol)
Keep your eyes peeled and watch for the Blackhawk to make port. Captain Billy Bowlegs and his Krewe will come ashore for a few hours. This will give younger bystanders, dressed in their best pirate costumes, an opportunity to meet the swashbucklers and take photos. If the krewe is feeling generous, they may even share some treasure with you. Then, junior pirates can join in the Little Scallywags Pirate Walk, as they plunder treasure while navigating their way through the sidewalks of downtown FWB. This is a fun and fantastic way to kick off the weekend.
After you and your youngsters are finished with your treasure hunt, head to one of the fantastic restaurants in the downtown area for dinner. We recommend Burrito del Sol, a coastal Mexican grill, or Ali’s Bistro for a traditional Italian dinner.
Pirate Landing & Skirmish
Date: Friday, May 15, 2026
Time: 5:00 PM–9:00 PM
- 5:00 PM: Vendor Booths & Food Trucks open at The Landing
- 6:00 PM: City of Fort Walton Beach “Concerts at The Landing” kicks off w/ Grace & Grit
- 7:00 PM: Pirate Landing & Skirmish
- 8:45 PM: Fireworks over the Sound
Location: Fort Walton Beach Landing – 131 Brooks St SE, Fort Walton Beach, FL
Be prepared for an evening filled with pirate festival fun as Captain Billy and some of his Krewe arrive by water at Fort Walton Beach Landing. But before they come ashore to scout out the city prior to their planned invasion on Saturday, you can enjoy the food trucks and vendor booths, starting at 5:00 PM. Then get in the festive spirit with a concert featuring Grace & Grit. At 7:00 PM, the mayor of FWB and his brigade will confront the pirate krewe—resulting in a skirmish. There won’t be any cannon fire, but there will be fireworks over the Santa Rosa Sound!
If you are looking for something fun to do before Friday’s festivities, consider a snorkeling tour with a local guide or a day at the Gulfarium Marine Adventure Park. Whether you are looking for the best activities for couples or family-friendly attractions, there is truly something for everyone.
Pirate Invasion
Date: Saturday, May 16, 2026
Time: 10:00 AM-6:00 PM
- 10:00 AM: Vendor Booths & Food Trucks open at The Landing
- 1:00-3:00 PM: Live Music on the Main Stage: Parker & Ivoree
- 3:30 PM: 70th Krewe of Bowlegs Pirate Landing
- 3:30-6:00 PM: Pirate Celebration
- 4:00-6:00 PM: Live Music on the Main Stage: The Aces
Location: Fort Walton Beach Landing – 131 Brooks St SE, Fort Walton Beach, FL
The mayor of FWB is desperate to stop the pirates, but Captain Billy Bowlegs and the entire Krewe come ashore and prevail. The festivities start early, with food trucks and vendors opening at 10:00 AM, followed by a fantastic lineup of live music. Full of mischief and merriment, the pirates and wenches will greet the fair citizens of Captain Billy's newly captured city. They may even be in the mood to share their loot with a few friends!
Depending on what time you plan to arrive at the festival, there may be time for a walk on the beach or sunbathing. With the private beach access at Seaspray Beach Vacation Rentals, this is the perfect way to start your morning or conclude the evening. We also have a large community pool and a grilling & picnic area for you to enjoy at the end of the day. Cook some hamburgers or a steak, watch the sunset, then take a refreshing dip in the pool. How could the day get any better?
Torchlight Parade
Date: Monday, May 18, 2026
Time: 7:00 PM
Location: Downtown Fort Walton Beach – Eglin Pkwy from First Street to Hughes Street, Fort Walton Beach, FL
The 70th Annual Billy Bowlegs Pirate Festival concludes with the legendary Torchlight Parade. Captain and krewe make their way aboard five floats and navigate through downtown. What better way to celebrate their 70th capture of Fort Walton Beach! Join the throng to watch the parade. With any luck, they will toss some of their treasure your way!
Since the parade doesn’t start until 7:00 PM, how will you spend your day? Consider adding a fishing adventure, a round of golf, or some retail therapy at our charming local shops.
Treasure Hunt
Dates: April 10-May 14, 2026
Are you ready to hunt for hidden treasures? Captain Billy hides coins throughout FWB for you to find! Each weekday, from April 10th through May 14th, a coin will be stashed in a new location. It is your job to follow the clues and find the treasure. You can scout for the clue each day on Facebook at 5:30 PM (with the exception of May 14th at 4:00 PM).
If you find a piece of the treasure, be sure to register it and be entered into a grand prize drawing!
Treasure is limited to two coins (maximum) per family, please.
A Message from Captain Billy Bowlegs:
“For safe treasure hunting, some rules and some regs.
ON NO PRIVATE LAND will you find any treasure.
NO DIGGING, DISMANTLING, or HARM… whatsoever!
You are looking for COINS designed to EXCITE!
They will be hidden BY, ON, UNDER or IN plain sight!”
Stay Near the Festivities at Seaspray
When you book your stay at Seaspray Beach Vacation Rental, you get the best of both worlds—you are on the beach and less than 2 miles to downtown Fort Walton Beach. We offer one, two, and three-bedroom accommodation in a family-friendly atmosphere. Whether you are coming for an unforgettable family vacation or are in FWB for work, our rentals are designed for comfort and offer a plethora of amazing amenities. There are even dog-friendly units for those traveling with a pet. Enjoy all that Okaloosa Island has to offer while relaxing in your home away from home at Seaspray.
Search for availability based on your preferred dates and book your getaway today!
Frequently Asked Questions
Q) Is the Billy Bowlegs Pirate Festival kid-friendly?
A) Yes. This is a family-friendly festival. However, where there are pirates, some mischief may be afoot.
Q) Was Billy Bowlegs a real pirate?
A) There is some debate as to whether the historical figure, known as Billy Bowlegs, was a real pirate. Some believe him to be William Augustus Bowles, but his pirate activity is harder to prove.
Q) Are there any other popular annual festivals held in Fort Walton Beach or the surrounding area?
A) Yes! There are quite a few annual events and festivals for you to attend. The Island Pier Spring Fishing Tournament is a local favorite. In the fall, don’t miss the Destin Seafood Festival.
Categories: