Vineyard Cup Marked by Mishaps at Sea
Steve Myrick

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.

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Stiff Breeze and Tough Competition, Vineyard Cup Brings Surprises
Steve Myrick

At the Vineyard Cup awards ceremony Sunday, which followed three days of spirited racing in Vineyard waters, it was Nantucketer Wendy Schmidt who took the top prize in the classic division.

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Vineyard Cup Regatta Set for This Weekend
Steve Myrick

The 11th annual Vineyard Cup is set to sail this weekend, with three days of racing in Martha's Vineyard waters. The annual Seafood Buffet and Auction precedes the sailing competition Thursday evening.

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By Boat or Foiling Kiteboard, Vineyard Cup Racers Find Fair Winds and Following Seas
Steve Myrick

In the grand tradition of the Vineyard Cup, the forecast for mostly fun, a high probability of good food, and a strong chance of evening music was spot on. The 10th annual regatta was a benefit for Sail Martha’s Vineyard.

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Holmes Hole Rocks the Vineyard Cup
David Lott
The just completed 2014 edition of the Vineyard Cup featured 66 competitors.
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Vineyard Cup, 90th Regatta Set Sail
Nicholas Bradley

Sailors and sailboats of every description will descend on Edgartown and Vineyard Haven this weekend when two big regattas that are mainstay sailing events of summer get under way.

The Edgartown Yacht Club will host its 90th annual regatta, and Sail Martha’s Vineyard will host its annual Vineyard Cup. Both events attract world-class sailors, and the waters from Cow Bay in Edgartown to West Chop in Vineyard Haven will be dotted with colorful sails all weekend.

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Vineyard Cup Brings Sailors of Every Stripe
Ivy Ashe

They came from as near as Oak Bluffs and as far as Denver to compete in the annual Vineyard Cup Regatta, held last weekend on Vineyard and Nantucket Sound and in Menemsha Pond.

Ninety-five boats and 485 sailors participated in three days of racing and three nights of revelry, all in the name of Sail Martha’s Vineyard, the Island’s youth sailing organization.

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