Vineyard Cup gets legs as major sailing event
It was fun, out on the water competing in the Vineyard Cup. But it was also frustrating to be on one of the largest boats among more than 70 vessels racing and looking at a lot of sterns from a vantage point trailing most of the fleet.
John Gerbstadt has sailed the east coast for more than a decade, living aboard, living the good life. But he was always a cruising sailor, not a racing sailor. This year the harbor around him was alive with competition, and the lure of the Vineyard Cup was strong. So he gathered up a willing and eager crew, including this newspaper reporter, and took the plunge into the world of sailboat racing with his 62-foot sloop Marilyn.
Organized by Sail Martha's Vineyard, the Vineyard Cup is growing fast. Last year about 40 boats competed. This year, more than 90 boats raced, including a large fleet of dinghy sailors, junior windsurfers, and a small but growing fleet of classic rowing gigs. With growth has come more attention, and more sponsors.
For the second year, Vineyard Vines signed on as presenting sponsor, and this year the regatta added Men's Journal as a host sponsor. Twenty other companies donated money, services, products, prizes, and expertise to make the event run smoothly.
Photo by Louisa Gould
"Our board realized, as we were growing, as our programs were growing, our fundraising needed to grow," said Sail Martha's Vineyard evangelist Brock Callen.
Money from sponsors and competitors fees help fund a wide variety of free and low-cost programs that introduce Island kids to the water and the world of sailing. "Having sponsors gives us a chance to do things we couldn't do any more than we could fly to the moon," Brock said.
Rounding a buoy outside the entrance to Edgartown Harbor, Marilyn lost a couple of hard-earned positions. Sailing a bit too wide around the mark allowed two competitors to slip past us on the inside.
But on the upwind leg, racing back to the large bell outside Vineyard Haven Harbor, spirits brightened considerably.
Photo by Steve Myrick
"We're moving like a freight train," John said from the helm. The crew let loose a whoop or two as Marilyn leaned into the stiff breeze and began to barrel past smaller boats with a rush. The skipper set his sights on Phra Luang, a fast schooner that wins more than its share of Island races. Then the crew noticed a tiny sliver of sunlight shining through the headsail, where no sunlight should be shining through.
While the Vineyard Cup is attracting more boats from afar, there is still a distinctly local flavor. "It brings a lot of people together for one cause," said Nat Benjamin, "getting kids on the water." On the second day of racing, Nat led the fleet across the finish line at the helm of Charlotte. The Gannon & Benjamin yard has turned out dozens of exquisite wooden boats over the years, many of which raced in this year's Vineyard Cup. So when Nat set out to build Charlotte for himself, everyone knew she would be beautiful. But would she be fast?
Photo by Louisa Gould
"We had always hoped," Nat said with a wry grin. Make no mistake. While he credited a crew with impeccable sailing pedigrees for the resounding victory, with every stroke of his design pencil, and every precisely laid plank, Nat was trying to build speed into all that beauty.
Against all hope, that little sliver of sunlight shining through the headsail seemed to be holding. The sail was parting along a seam repaired the night before the race. There hadn't been enough time to make proper permanent repairs, so John had the sail patched together temporarily. It was a gamble from the start, and Marilyn seemed to be bucking the odds. She closed on Phra Luang, and the rest of the field, with surprising tempo.
Photo by Steve Myrick
Then there was a sound like a muffled explosion, the boat shuddered for a moment, and she began to decelerate like someone stomped on the brakes. The headsail was luffing wildly in shredded tatters.
The boats Marilyn had left in her wake a few minutes earlier now began to overtake her.
With just the mainsail left to power the boat, the only strategy left was to make lunch, sit back, and finish the course. Which John and his crew did, with a vow to return for next year's Vineyard Cup.
Click here to see the overall results for the Vineyard Cup.
Click here to see the Vineyard Cup results by class.





