The 12th annual Vineyard Cup may go down as the most adventurous in the history of the event, with day one of racing scrapped because of violent weather and three boats dismasted in the second and third days of the event.

More than 60 boats competed in the regatta that benefits sailing programs for Island kids at Sail Martha’s Vineyard.

But by all accounts this year was a wild ride.

On Sunday, Don Cohan’s Etchells class Encore was dismasted in stiff seas off East Chop near the conclusion of the race, according to race officials. Both Oak Bluffs and Vineyard Haven harbor masters responded to the dangerous situation. The vessel was towed back to shore for repairs.

Race start on Saturday was all elegant lines. — Mark Lovewell

Less than five minutes later race director Ellen Pesch, aboard the committee boat, said she was shocked to hear competitors reporting by radio that Sophie, a 91-foot classic sailing yacht owned by Will Duffell of Portsmouth R.I., had her massive carbon fiber mast crash down into the water. There were 20 people aboard.

“Sophie was far enough out we ended up getting the Coast Guard involved,” Ms. Pesch said.

Two salvage vessels towed the yacht toward New Bedford for repairs as the rest of the fleet finished Sunday’s pursuit race. No one was hurt in either incident, race officials said.

On Saturday, Jim Pringle of Vineyard Haven was off Edgartown at the furthest point in the 15-mile course when the mast gave way aboard his 25-foot boat Myfanwy.

“It came down in the water,” Mr. Pringle said. “Nobody got hurt,” he added with a shrug.

Ms. Pesch made the call to cancel Friday’s racing after weather observers spotted water spouts south of the Vineyard amid intense rain and wind in Vineyard Sound.

Among the Vineyard Cup overall division winners was the Tartan 43 Morfeus, whose crew preferred Sunday’s 20-plus knot winds to the calmer breeze on Saturday in the PHRF non-spinaker second division.

“That’s what makes it fun,” said Dee Wilson, who crewed with his sons Todd and Donald for skipper Peter Schwebach.

“When you are out here competing, having big air makes it exciting,” Mr. Schwebach said.

But competition is only one of the aspects of the Vineyard Cup this crew enjoys.

“I love the low-key, down-to-earth quality environment, without being too racey,” Mr. Schwebach said. “Quality people.”

Among the other division winners was Santana, a Sparkman & Stevens 55 owned by Wendy Schmidt of Nantucket. Santana also won last year’s classic division.

Stuart Halpert of West Palm Beach, Fla. won the PHRF non-spinnaker first division with Providence, an Alerion 28. Vineyard Haven residents Mo and Pam Flam were a close second in their Alerion 28 Penelope.

In the PHRF spinnaker class, Island ace Stephen Besse took top honors in Apres.