Monday, September 14, 2026

Hometown: Register to Sail in Fifth Annual Cardboard Boat Regatta

Homemade ships compete in last year's Cardboard Boat Regatta, which raises money for Big Brothers Big Sisters (Photo courtesy of Williamsburg Jaycees)
Homemade ships compete in last year’s Cardboard Boat Regatta, which raises money for Big Brothers Big Sisters (Photo courtesy of Williamsburg Jaycees)

 

For four years, locals have set sail in special vessels for a day of pirates and philanthropy.

The boats might not survive the journey, but the seafarers leave with the satisfaction of supporting area children.

Spots are open now for the fifth annual Cardboard Boat Regatta, with registration fees doubling from $30 to $60 after July 15. Although previously setting sail in July, this year’s race will be held Aug. 2 at the Watermens Museum in Yorktown.

boats 2The Williamsburg Jaycees, a group of community members ages 21 to 40 committed to service, are steering the event. The regatta benefits Big Brothers Big Sisters of the Greater Virginia Peninsula and its mission of providing positive adult figures in the lives of local children.

“The annual Cardboard Boat Regatta is the most unique way to have some fun while supporting a great cause,” said Jason Blanchard, event coordinator from the Jaycees, in a news release. “It is the only event to combine engineering, athletic ability, and soggy cardboard!”

Those who sign up are set to task to build their own boats out of cardboard. The race itself is run in bracket-style based on the ages of each crew, and boats should be constructed to withstand multiple voyages.

Ayanna King, BBBS CEO, called the regatta a “comical event” and said her organization’s mentors and children love participating.

“To see everyone’s ingenuity and creativity always makes for interesting races,” she said in the release.

Prizes go to the first-place finisher as well as a People’s Choice award for best boat design. The Titanic Award goes to the team with the most dramatic or entertaining sinking.

For those taking a swashbuckling approach to seafaring, the event concludes with a final no-holds-barred race where sailors are invited to use any means at their disposal — water guns, buckets or other pirate methods — to slow opponents. The first boat over the finish line earns the Pirate Award, with its crew crowned Pirate King and Queen of the Regatta.

Shipmates can start as young as 5 – those under 10 must be accompanied by an adult – with two sailors per boat.

Registration closes July 31. For more information or to register, visit the Jaycees website or call 243-6695.

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