First, there was a challenge.
Last summer, Edward Miller and Blake Middleton of Chilmark brought their boats to Edgartown and sailed in what’s known as the Nationals: the Edgartown Yacht Club’s annual race featuring Herreshoff sailboats from across the region. Clubs from Beverly, Marion, Buzzards Bay and Shelter Island all participated. Mr. Miller and Mr. Middleton typically sail their Herreshoffs in the annual Menemsha Pond Races, a long-standing up-Island tradition.
But in Edgartown, the pair had such a good time that “we decided we would challenge the Edgartown Yacht Club to a race on our home course,” Mr. Miller said in a telephone interview last week. Only Herreshoffs would be used, and the match would last a full weekend, with three races on Saturday and two on Sunday. The winning team would earn bragging rights as well as a trophy.
The challenge, issued last fall, was accepted. The first-ever Vineyard Herreshoff Cup takes place this weekend.
“The spirit of it all is to have fun and enjoy it,” Mr. Miller said. “We hope this will become an annual event that grows in popularity.”
Since the race call for entries, there has been a second challenge, however. The Menemsha fleet of Herreshoffs is competing on familiar ground; the boats are already on their moorings. The Edgartown sailors faced the perplexing task of getting their Herreshoffs to the pond in time to race.
“Nobody’s sailing, because you can’t get there,” said Diana Dozier of Edgartown. Tides and prevailing winds prevent the actual sail, she said, although she noted that sailing back is less of a concern.
“The tides are supposed to be with us — I say us because we’re a team — all the way back,” she said. Some boats would be trailered over, while others would be towed, Mrs. Dozier added. As far as she knew, none of the Edgartown team had ever sailed in Menemsha before.
“It’s going to be a kind of a new experience,” said John Stevens of Edgartown. “I would say the local sailors up there have an advantage, at least the first race or so.
“But we’ll do well,” he said. “We have a good collection of skippers and crew.” Each boat must be sailed by two people.
The race is as much a challenge as a celebration of the Herreshoff 12 1/2 design itself, which turns 100 this year. The design is one of dozens created by Nathaniel Greene Herreshoff of Bristol R.I. It is a gaff-rigged boat with a keel, and although early models were made of wood, most are now fiberglass. Mr. Miller’s boat, Crow Dancer, is a wooden 12 1/2 modeled after one of the first 20 Herreshoffs ever made.
“It’s a boat that’s small enough . . . where it’s manageable to store over the winter, but large enough that you can take some of the family members out,” Mr. Stevens said.
“Especially on the Vineyard, it’s a wonderful tradition,” said Brock Callen of Sail Martha’s Vineyard, which will be managing the race this weekend. “They’re boats that have been here for generations and they kind of say Vineyard even if it’s not a Vineyard design,” he added.
“It sails differently from any other boat,” Mrs. Dozier said. “You can be a great sailor in a lot of other boats and spend five years learning to sail this one.” And it doesn’t sink, she added.
“They’re just lovely boats,” Mr. Callen said. “It’s not the fastest in the world, but certainly the folks that race them enjoy it.”