The sixth annual Vineyard Cup regatta was the best yet. Wind, weather, participation and competitive spirit reached new levels in what has become the Island’s premiere three-day sailing competition. A record 101 sailboats of varying size and construction competed in Vineyard waters, from Menemsha Pond to Cow Bay.

There was series racing, handicap racing and pursuit racing. The top winner of Sunday’s pursuit race was Ishmael, a 45-foot schooner built in 1929, owned by Fred and Sarah Murphy of West Tisbury. He is a skilled Vineyard merchant captain who has sailed the Pacific and Atlantic in ships as big as 700 feet in length. Mrs. Murphy is an educator at the West Tisbury School.

“It was very exhilarating,” said Mr. Murphy, after the race. “We have always won second or come from behind. We’ve always been behind somebody. It was great being ahead of everyone and anybody,” Mr. Murphy said.

The Murphys have owned the beloved schooner for 37 years. On Sunday, on the boat, the captain was surrounded by friends as crew: his daughter Grace, Scott Young, Ross MacPherson, Ben Hannigan, Liz Packer, Margeries Lau and Tom Rancich.

With a Pursuit Race format, the starting times are different (slowest earliest in the start, fastest latest in the start), adjusted so that all the boats theoretically will cross the finish at the same time. There were more than 60 boats competing in that Sunday race, when Ishmael pulled ahead of them all.

Catboat fleet sets out for Saturdays Sail — Louisa Gould

“I’d say that our pursuit race is our signature race,” said Brock Callen, program director for Sail Martha’s Vineyard, the organization hosting the race. “It is a wonderful format that isn’t done frequently enough.” Compared to a handicap race, Mr. Callen said: “You know you are winning if everybody is behind you. You know you are losing if everyone is in front of you. Pursuit racing is a real test of the handicap system, and it worked perfectly.”

There was racing on Friday and Saturday. There were boats as small as Herreshoff 12 1/2 sloops racing in Menemsha Pond. There were boats as big as the 91-foot schooner Alabama racing off West Chop.

On Saturday, the century-old 45-foot sailboat Violet won the day of racing in the classic division. The ketch, built in Scotland in 1911, and restored on the Vineyard in 1991 by her captain, Gary S. Maynard, and his wife, Kristina Kinsman, is a Vineyard favorite. Many were pleased she did so well. The couple lives in Chilmark.

The winds suited the sailors. “It varied. On Friday we had from seven to nine knots, on Saturday we had ten to 13 knots. And Sunday we had from 15 to the 20s,” Mr. Callen said.

sailboat spinnaker
Spinnaker Flying high in ideal winds. — Louisa Gould

Every day was sunny and there was plenty of evidence of sunshine on the red faces of competing sailors when they gathered under the tent at the Beach Road Extension. The headquarters for the competition was in that narrow street that opens to a stellar view of the harbor, next door to the Black Dog Tavern. For three nights, the captains and their crews gathered to share their stories of the day and to pay attention to the notices and find out who was a winner.

Mr. Callen said the sailors came from all around the region, from Maine, the North Shore of the Cape, down to the Chesapeake Bay. Full results are available online at