Racers set sail for Martha’s Vineyard and Vineyard Cup Regatta

Classic catboats, shown here in last year's Vineyard Cup, are set for a parade of sail and racing Saturday, July 14. — File photo by Louisa Gould

Eighty boats ranging from 16 feet to 126 feet, with crews spanning skill levels from novice racer to past national champions, amateur and professional, Islanders and visiting sailors, and very likely, a few pets, are set to sail in the Vineyard Cup Regatta that begins Friday.

More boats are expected to sign up for the sixth annual Vineyard Cup as Friday approaches. Entries will remain open online until midnight, Thursday.

Three days of racing are scheduled among four classes, including the classic division, which draws many of the beautiful wooden boats that call Martha’s Vineyard harbors home.

Among them will be Ishmael, a 48-foot schooner owned by Fred and Sarah Murphy of Vineyard Haven. Ishmael ranked first overall in the classic division last year.

“It’s fun, with a little touch of competition,” Mr. Murphy said. “You meet some people that come in for the race. Some could be much more competitive, but they come because it’s a great get-together, and go sailing. It’s not real heated.”

While the boats compete in separate divisions, it is not unusual to see most of them on the race courses at the same time. There are not many regattas where you see a classic schooner running down-wind alongside a sleek high-tech racing boat, but those sights abound in the Vineyard Cup.

Race organizers encourage Islanders and visitors to watch the races from shore. Among the best vantage points for Friday (1 pm start) and Sunday (10:30 am start) races are Eastville Beach, where the races start, and East Chop Light, which offers a higher vantage point for boats sailing east into Nantucket Sound. On Saturday (various class starting times from 10 am to 11:00 am), competitors will start off East Chop, but turn west and sail down Vineyard Sound toward Quick’s Hole, so West Chop will be offer good views.

Joseph P. Sylvia State Beach is also a good bet for race watching, because three of the five designated courses will take the fleet just off that shoreline. The actual course is not designated until just before the race.

Saturday will also feature a parade of sail for the classic vessels beginning at 10 am. Any vantage point around Vineyard Haven Harbor should offer great views.

Race director Brock Callen said the organizers will make a strong effort to post information about courses and other events online at the Vineyard Cup website (vineyardcup.com) and its Facebook page.

Each day of racing is followed by a raucous awards ceremony and post race party under a big tent in front of the Black Dog Tavern. The public is not only invited, but encouraged to attend the parties. Food prepared from the Black Dog kitchen is featured, along with various libations served from an ice-filled skiff in the middle of the uproar. The cost for all three nights is $75, for one night, $30.

Proceeds benefit Sail Martha’s Vineyard, a nonprofit organization that offers sailing instruction to more than 400 kids each summer, and supports the Martha’s Vineyard Regional High School sailing teams, as well as a high school maritime vocational program, among other programs and events.