Thursday, October 1, 2026
The Nautical Mile in Freeport is expected to come alive Sunday from 12 to 6 p.m. with swashbuckling excitement as the community prepares for its first Pirate Fest, a soon-to-be annual event designed to extend the vibrancy of the waterfront district well beyond the summer months.
Organized by a coalition of local vendors, the Freeport Chamber of Commerce, and the Nautical Mile Business Organization, the festival promises to be packed with family-friendly fun, community spirit, and a hearty dose of pirate-themed adventure.
A ribbon-cutting ceremony will kick off the festivities at noon in front of the chamber’s office —where Sapphire Yacht is docked — and a lively boat parade will launch the event. Both private and commercial vessels will be transformed into pirate ships, parading through the canals and bays for up to an hour.
Freeport’s inaugural Pirate Fest could become a beloved new tradition, ensuring that the Nautical Mile remains a destination for fun and adventure all year long, according to organizers.
“We are doing it to remind people that even though the summer is over, the fest, the Nautical Mile is jumping,” said Robyn Workman, owner of the local Sparkle on Stage Cultural Arts Center and one of the event’s chief organizers. “There’s still things to do down here.”
The Pirate Fest is the brainchild of a group of local business owners who, during a brainstorming session, sought ways to attract visitors during the off-season.
“A few of the vendors and I were sitting and talking about what we could do in the off months,” Workman explained. “How do we attract people to come down? And a few ideas were being bounced around.
“Pirates are fun,” she added, “and that’s how that really came to fruition.”
Festival attendees could look forward to a variety of activities, including a scavenger hunt, taking participants to different restaurants and businesses along the Nautical Mile. Those who complete their maps by collecting stamps at each location can return to Sparkle on Stage to claim their “pirate booty”— consisting of prizes for children and gift certificates for adults.
For those eager to embrace their inner buccaneer, pirate costumes are highly encouraged, with prizes awarded for the best-dressed adults and children.
On the water, a catamaran stationed at the esplanade will offer lessons on wrapping and unwrapping sails.
The Freeport Water Taxi will provide one-runner tours, and Sparkle on Stage will host a Kids Cove with arts, crafts, games and karaoke.
A highlight of the day will include four magic shows performed by two swashbuckling magicians, Captain Alexander and Captain Melissa, with performances scheduled at various locations, including Halfway Down, My Little Town Childcare, Sparkle on Stage and, weather permitting, the esplanade.
“Ahoy mates,” Mack from Hurricane Harry’s, a restaurant on the Mile, said in an email about the event. “I’m excited — let’s pack the deck for the boat parade!”
The event is supported by a wide array of local businesses, including Puerta Plata, Halfway Down, My Little Town Childcare, Scoops, Sparkle on Stage, the Water Taxi, Captain Lou’s Fleet, Sapphire Yacht, Being Calm Wellness, Catamaran Services, and more.
Organizers expressed hope that Pirate Fest could become an annual tradition, helping to keep the Nautical Mile bustling throughout the year.
“Our goal is to let people know there’s fun stuff coming,” Workman emphasized. “And then there will be other festivals going on, hopefully in April, and different restaurants will be doing different events throughout the months that are not just summer months.”
