Tabasco (from schooner Juno), captained by Zoli Clarke, just after almost losing her rig off of West Chop in the first leg of the race on day one. —Chace Lewis 
Saphira, a 91-foot boat built by Brooklin Boat Yard in Maine, “running,” or sailing, southwest down the Sound. —Chace Lewis 
Bear Harding’s boat, the Aldebaran, which he bought last year to run a charter business out of. —Chace Lewis
It was a reunion of seafarers last weekend when the Vineyard Cup Regatta, a great annual sailing race around the Island, celebrated 20 years.
Hosted every year by Sail Martha’s Vineyard, many local sailors compete in the Island race that is also a fundraiser for the Tisbury-based nonprofit’s youth sailing groups.
Before the races over the weekend, on Thursday, June 9, the 35th annual Sail MV Seafood Dinner and Auction fundraising banquet was held at the Tisbury Wharf in Vineyard Haven. Andy Nutton, executive director of the nonprofit and race organizer, said they raised just under $10,000 for youth sailing groups.
Nutton said he was pleased with the race’s results, and that the weekend went as expected.
Sailors involved in the regatta, Nutton said, mostly come from within the local sailing community. The participants know the waters well, and it is mostly a calm, relaxing race, he added.
The good weather, though, was a bonus; Friday’s sunshine carried on into Saturday, which was previously forecast for rain.
The race started Friday, June 10, at noon in Vineyard Haven Harbor, and with partly cloudy skies and 80° weather, sailboats could be seen all day on the horizon dotting the Vineyard Sound.
Saturday’s weather was as peaceful as Friday’s conditions, and a light breeze started the day and picked up through the afternoon.
Alex Goldhill’s Mah Jong, a 52-foot Sparkman and Stevens yawl made mostly of teak, originally built in 1957 at a shipyard in Hong Kong, but restored by builders at Gannon & Benjamin in Vineyard Haven, won the Classics class, and took first place both Friday and Saturday.
“The wind was fairly light in the harbor but picked up as we went past West Chop. We had a nice downwind leg on the sail back to the finish line,” Luke Sederholm, Mah Jong crew member, said of the Friday race. “I thought it was a great race. We had very good wind and weather compared with other years I’ve done it.”
On Friday, sailors raced 11.9 nautical miles in a fleet race, where boats all start at the same time. Mah Jong’s journey to first place on Friday was 11.9 nautical miles, taking 1 hour and 58 minutes. But on Saturday, the race was a pursuit race where the slowest boat starts first, working back to the fastest boat starting last. The race on Saturday was 14.8 nautical miles, and lasted 5 hours and 5 minutes for the Mah Jong. All classes of boats compete in the Vineyard Sound or Nantucket Sound besides the Catboat Division, which stays in the vicinity of Vineyard Haven Harbor.
First place in the Modern Classics class was Karena Hammarlund’s Maitland, a Herreshoff Buzzards Bay 25, a wooden racing sloop. Maitland finished its race Friday morning in first after sailing for 2 hours and 7 minutes, finishing with a corrected time of 1 hour and 23 minutes. The Maitland finished second in its race Saturday morning. In sailing, corrected time is a sailboat’s finishing time after a handicap adjustment is applied. The boat with the lowest corrected time wins, even if it crossed the finish line later.
Coming first in the Schooner class was Lars and Peter Forsberg’s Spirit, which is an Alden Schooner, a traditional sailboat designed by American naval architect John G. Alden. Spirit finished in 4 hours and 59 minutes in its Saturday race to earn first place in the Schooner class.
In first place in the Spirit of Tradition class was Zebra, a W Class 46, a lightweight carbon-fiber rig with foils below, owned by Frank Sutula. Zebra finished in exactly 4 hours and 52 minutes on Saturday, beating the second-place boat Saphira by only 42 seconds.
Finishing first place in the Vintage class was Trevor Fetter’s Black Watch, a custom yaw, a unique, two-masted sailboat where the rear mast is positioned aft of the rudder post. Black Watch came in second in its race on Friday, but won on Saturday with a time of 4 hours and 1 minute.
In the Non-Spinnaker class, Adam T. Hayes’ Bliss won. Bliss, riding on his J35c, finished first on both days it raced. On the first day, Bliss finished in 1 hour and 39 minutes and a corrected time of 1 hour and 29 minutes. On the second day, Bliss finished with a time of 4 hours and 49 minutes.
In the Spinnaker class, Stephen Besse’s Après won first place in the class on a J/120. On the first day, Après finished second in its race, but on Saturday, Besse finished first in its class with a time of 4 hours and 8 minutes.