Bremerton’s first annual Pirate Festival held at Quincy Square
Published 1:30 am Monday, March 2, 2026
People of all ages dressed up in their best pirate costumes, hooks, and hats Feb. 28 for Bremerton’s first annual Pirate Festival at Quincy Square.
A showing of Pirates of the Caribbean: The Curse of the Black Pearl was held at the Roxy Theatre with special guest and actor Isaac Singleton Jr., who played Bo’Sun in the film. Vendors, food booths, and live music lined the street, providing entertainment and family fun. Singleton Jr. offered a free meet and greet after the film, along with free photos and autographs as well.
Mayor of Bremerton, Greg Wheeler, was in attendance to introduce the showing of the film at Roxy.
Proceeds from the festival went toward the restoration of The Lady Washington, the boat featured in the Pirates of the Caribbean. The ship is primarily located in Aberdeen, operated by Grays Harbor Historical Seaport. The brig replica that was built in 1989 has been seen in films other than Pirates of the Caribbean, including Star Trek: Generations, Once Upon a Time, The Great American West, Blackbeard, and Revolution.
The festival, free to the public, was hosted by Esther Chilcutt and the Kitsap Pirates, a group on the Kitsap Peninsula that focuses on charity, entertainment, and events that bring the community together. The Roxy Theatre and local vendors helped fund the festival.
Kitsap Pirates aims to continue growth and become a non-profit organization, Chilcutt said. The group plans to continue the pirate festival in years to come, as well as host other events. “We want to run a Fall masquerade Ball, perhaps at the Van Zee building at the Kitsap Fairgrounds,” said Chilcutt. “Perhaps a Midsummer Night’s Dream Fairy festival. There is a lot of crossover in the community of pirates and fairies, think Peter Pan.”
Kids were able to magically turn into their pirate-selves with make-up and live action role-play, where they were given gold that they could spend on items at the festival. There were booths where kids could create their own pirate bandanas, transforming themselves into another world.
“[The festival’s mission is] putting together a free event for families, bringing aspects of conventions like actors and exhibits of film, props, etc., and fundraising and raising awareness of local history, programs and services,” Chilcutt said.
