For Rique Gwin, serving as Captain Billy is more than a ceremonial title. It’s a way to give back to the community he and his wife chose as their permanent home.

• Gwin and his wife Kelly, both retired from the Air Force, first moved to the area in 2000. After several relocations tied to military service, they settled in Fort Walton Beach for good. Gwin retired eight years ago, with Kelly following about two years later.

“The people here were just so welcoming, and we just loved the community, and especially the people in Bowlegs were just awesome,” Gwin said. “So we made this our home.”

The couple’s involvement with the Krewe of Bowlegs began through friends whose child attended school with their daughter. After being sponsored into the Krewe, the Gwins served as general members for nearly a decade before being asked to serve as first mate and first mistress for Buddy Carter during year 65 — a role extended to two years due to the COVID-19 pandemic.

The Krewe was originally established 70 years ago to support the Water Ski Festival, an event created to promote tourism along the Emerald Coast and boost local businesses, according to Gwin. That tradition has evolved into the Billy Bowlegs Pirate Festival, named after legendary pirate William Augustus Bowles, with dates adjusted over the years to align with periods when the area benefits most from added tourism.

Gwin said the Krewe’s reach now extends well beyond festival weekend. Members travel as far north as Minnesota and as far south as Central Florida to attend events hosted by other social krewes, building relationships that bring visitors back to Fort Walton Beach.

• “Right now we might be around 150 room nights worth of visitors that we’ve personally invited that are coming in for this coming festival,” Gwin said. “And that’s just the ones that we know of the reservations they’ve made, much less all the other economic impacts in the area.”

Throughout the year, Krewe members read books to schoolchildren, help present quarterly awards on Eglin or Hurlburt Field and participate in other community outreach efforts.

“That, to me, that’s kind of our purpose, is to be a good ambassador for Fort Walton Beach,” Gwin said.

This year, the Krewe is also paying tribute to the military heritage of the local area. As an official member of the Okaloosa County America 250 commission, the Krewe has incorporated patriotic elements into many of its festival events — a fitting addition for a celebration led by a retired Air Force veteran in a community shaped by nearby military installations.

“What an honor it is to represent that heritage on the 250th anniversary of our nation,” Gwin said.

This year’s festival introduces new elements through the William Augustus Bowles Museum & Historical Foundation, a separate historical organization staffed largely by Krewe volunteers. The foundation will award scholarships to local high school students, sponsored by David Scott Lee dealership. 

The foundation also organizes the festival’s treasure hunt. For 30 days leading up to the festival, volunteers have hidden coins throughout the area — from Niceville to Mary Esther — with daily clues guiding hunters. On Thursday night of festival weekend, Gwin will select a winner from the 30 coin recipients to receive a prize.

“Every day is like a second full-time job to try to get this thing put together,” he said. “It’s a fun thing to do. It takes a lot of effort, but when you see it all come together, see the kids’ faces and all the people at the landing super excited, it really is worth every bit of effort you put into it.”

For Gwin, hosting the event in a thriving downtown carries personal meaning.

• “I purposely made this my hometown,” he said. “I think it’s wonderful to see the downtown Fort Walton Beach thrive and give us a great venue with the newly renovated Landing Park for all the social things we want to do, but also be proud of our local area because we have a lot to be proud of.”

Festival schedule

The 70th annual Billy Bowlegs Pirate Festival, presented by Felicity Plastic Surgery, runs from Thursday, May 14, through Monday, May 18.

Thursday, May 14 – Pre-Invasion

• 4 to 6 p.m. – Little Skallywags “Meet The Pirates” with downtown merchants along Miracle Strip Parkway

Friday, May 15 – Skirmish

• 5 to 9 p.m. – Billy Bowlegs Festival at the Landing
• 5 p.m. – Vendor booths and food trucks open
• 6 p.m. – City of Fort Walton Beach Concerts at the Landing featuring Grace & Grit
• 7 p.m. – Pirate Skirmish
• 8:45 p.m. – Fireworks

Saturday, May 16 – Pirate Invasion

• 10 a.m. to 6 p.m. – Billy Bowlegs Festival at the Landing with vendor booths and food trucks open all day
• 1 to 3 p.m. – Parker & Ivoree on the Main Stage
• 3:30 p.m. – 70th Krewe of Bowlegs Pirate Landing
• 4 to 6 p.m. – The Aces on the Main Stage

Monday, May 18 – Torchlight Parade

• 7 p.m. – Billy Bowlegs Torchlight Parade, hosted by the Greater Fort Walton Beach Chamber of Commerce. The parade route runs along Eglin Parkway between First Street and Hughes Street.

Other festivities throughout the weekend include the treasure hunt, an arts and crafts festival and food from local food trucks.

“Definitely come out on Friday and Saturday,” Gwin said. “It’s themed on Bowlegs, but there’s so many other things going on as well. There’s a lot of opportunities for fun for kids and for adults as well.”