The traditional end of summer Herreshoff Cup Race included a twist this year, with the Vineyard Haven Yacht Club competing in the race for the first time and playing host. Usually the event is an up-Island versus down-Island competition, pitting members of the Edgartown Yacht Club (EYC) against sailors from Menemsha Pond.

Stuart Halpert of Tisbury recently helped found the Vineyard Haven Yacht Club’s Herreshoff Club, and suggested his club host the event this year, in part, because Vineyard Haven harbor is located conveniently between the race’s traditional competitors.

Twenty-two boats competed over the weekend, all Herreshoff 12 1/2 Footers, a one-hundred-year-old one-design keelboat that has long been a fixture in New England waters. Its four-sided sail is bound at the top by a spar called the “gaff” that runs oblique to the mast and makes the vessel instantly recognizable among other ships of its class.

“It is often thought to be one of the most elegant boats ever designed,” Mr. Halpert said. “I will tell you that it is a quintessential New England sailboat. A small one but terribly classic.”

Racers from Menemsha, Edgartown and Vineyard Haven competed on Saturday and Sunday. — Mark Alan Lovewell

Saturday saw light wind conditions on the harbor, and a bit more interference from ferries and motor vessels than the usual courses in Menemsha Pond and Edgartown harbor. But Sunday brought “champagne sailing conditions,” according to principal race officer Ellen Pesch. Clear skies and a steady wind carried through for both races.

The Edgartown Yacht Club team took home this year’s trophy, which is awarded by aggregating the scores of the three fastest ships from each competing town’s fleet. Edgartown sailors Deb Orazem of June Bug and Warren Vose of Moonglade won all five of the weekend’s races. Ms. Orazem took first place in all three races on Saturday; Mr. Vose won both races on Sunday. Mr. Vose also took the weekend’s lowest overall score.

Don McLagan of Chappaquiddick, a poet and former entrepreneur, has been racing his Herreshoff 12 1/2 since 1995. He competed this weekend with his daughter, Marnie McLagan. Mr. McLagan joked that while a four-sided sail may be hard to manage (“a four-sided sail is the work of the devil”) the Herreshoff is a boat that almost anyone can pick up with a little practice.

Mr. Halpert said that the Herreshoff can be sailed at eight years old or at 80. Indeed, the weekend featured a few sailors approaching or indeed already within their octogenarian years.

At an after-race dinner at the Vineyard Haven Yacht Club Saturday evening, Mr. Halpert encouraged all the racers to sit with someone from one of the opposing clubs to get to know them better.

“[The race] is really a lovely coming together of people who have an anchor — no pun intended — in Menemsha, Edgartown and Vineyard Haven,” Mr. Halpert said.

He said he hopes that the three-way race continues going forward on a regular basis.