Sail Martha’s Vineyard is expecting more than 100 sailboats this weekend at Vineyard Haven harbor as the 2014 Vineyard Cup gets underway.

West northwest winds and a flooding tide combined to create a tough go on Sunday as the Holmes Hole fleet took to the Sound for two races. HHSA racers have already seen more of Course #2 in 2014 than in the previous 10 years, and the elements made it memorable.

Sail MV hosts its major fundraising event at the Tisbury Wharf with the harbor as a backdrop beginning at 5:30 p.m. on Thursday, July 10.

The Edgartown Yacht Club hosts its 91st Annual Regatta beginning July 10 and continue through July 12.

Sunny skies and crisp summer breezes combined with two full days of stellar competition as the Menemsha Pond Racers won the inaugural Vineyard Herreshoff Cup this weekend.

The competition was held June 28 and 29 on Menemsha Pond and featuring sailors from the Edgartown Yacht Club and the Menemsha Pond Racers.

The first-ever Vineyard Herreshoff Cup takes place this weekend. "The spirit of it all is to have fun and enjoy it," Edward Miller said. "We hope this will become an annual event that grows in popularity."