Vineyard Haven Harbor dazzles

Herreshoff 12.5 regatta brings Island sailors together.


Scattered throughout the Vineyard Haven Harbor this weekend were 22 traditional Herreshoff 12.5 sailboats, competing for the win in the 2022 Vineyard Herreshoff Cup.

After five races comprising three Island fleets, Edgartown came out on top in the two-day Herreshoff 12 class Regatta, with frontrunner Warren Vose, skipper of ‘Moonglader,’ earning just 17 points. Menemsha Pond Racers and Vineyard Haven Yacht Club came in second and third, respectively.

Vineyard Haven Yacht Club made its debut participating in the annual event, as the regatta initially consisted of only Menemsha Pond Racers and Edgartown Yacht Club Herreshoff 12.5 boaters.

The Herreshoff 12.5 is the “quintessential New England boat,” Vineyard Haven resident and regatta entrant Stuart Halpert told The Times. Deeming it “uncommonly popular,” Halpert said the Herreshoff boats have continued its unique prevalence for over a century, as it is easily sailed by novices and experts alike. 

Because of its smaller size, the Herreshoff 12.5 can easily maneuver within the harbor’s waters, allowing spectators to enjoy the visceral sailing race without ever leaving land. 

Designed for New England waters by architect Nathanael Herreshoff, the namesake boat’s 12.5 size is wildly versatile, and “great fun to sail,” said Halpert. “You can be as sophisticated as you want with them, and you can be as simple as putting out the sail [and the] tiller.”

Multiple scored races over the two- day period reveal the winning fleet–and the winning boat– The winner of the regatta is determined by calculating the sum of the scores of the top three finishers from each club. The lowest number of points wins (akin to golf scoring).

EYC ‘Moonglade’- Warren Vose/Anne Vose: 17

MP ‘Pippin’-Robert Soros/Scott DiBiaso: 20

EYC ‘June Bug’-Deborah Orazem/Penn Edmonds: 22


Edgartown Yacht Club: 79


Vineyard Haven Yacht Club: 149