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.

“It’s hugely pleasing and somewhat humbling to watch this community rally around Sail Martha’s Vineyard,” program director Brock Callen said on Monday after the racing was over. He praised the efforts of the regatta’s group of volunteers and the support of its sponsors.

Sail Martha’s Vineyard, a nonprofit organization that provides free or low-cost sailing instruction to Island youth and has no endowment, depends on fundraising efforts and the contributions of donors throughout the year. Sponsor support of the Vineyard Cup allows for all entry fees and racing party bracelets funds to go directly into Sail Martha’s Vineyard programs. This year, local bands DCLA and Entrain performed at the nightly post-race awards parties.

“It’s a great institution,” said Edward Miller of Chilmark who sailed in the Cup. “I know of many people that came over . . . from the mainland, just because it’s a great destination.”

Mr. Miller sailed his Herreshoff Crow Dancer to first place in the Menemsha Pond races over the weekend (he placed second last year). The Menemsha Pond race in the Cup is part of an ongoing series of traditional races at the pond that last throughout the summer and started in the 1970s.

Steve and Pam Besse, winners of non-spinnaker division in Vineyard Cup. — Louisa Gould

Saturday featured the bulk of the Cup races, and began with a parade of sail in Vineyard Haven harbor, with the catboats and small wooden boats led by harbor master Jay Wilbur’s patrol boat. Mr. Wilbur’s boat announced the start of the day’s festivities by spraying a huge geyser of water from the fire hose on the patrol boat. The hose pumps about 500 gallons of water per minute, he said, and draws a great deal of attention when in use.

Approaching the finish: winner of the spinnaker division, owned by Donald Tofias. — Louisa Gould

“Sailboats are pretty common in Vineyard Haven. So you might not even notice a parade [otherwise],” Mr. Wilbur said.

“Everybody seemed to love it,” he added. “I’ve never seen such broad smiles on people’s faces . . . as when we’re doing that.”

There were five courses for the various divisions of competitors sailing on Vineyard and Nantucket Sound.

Martha’s Vineyard Shipyard owner Phil Hale, who placed first in the non-spinnaker division one race with his Shields sailboat Wicked (crewed by son Rob and friend Greg Johnson, who was in town from Dallas), praised the race committee’s course selection.

Same wind, different tacks; boats crisscross during Vineyard Cup race. — Louisa Gould

“It was a great weekend for sailing,” Mr. Hale said. “The wind was a little up and down, but they can’t control for that.”

Mr. Hale, a member of the Sail Martha’s Vineyard advisory board, has participated in every regatta since the Cup’s inception.

“[This year] we sailed that boat just as hard and as technically correct as possible,” he said. “I think that speaks to the level of competition at the Vineyard Cup.”

Saturday’s races started under slow conditions, with the boats facing a light air for much of the day “until the sea breeze came in,” Mr. Callen said. “That was frustrating for some sailors . . . but we got most of the boats across the line in the time limit.”

Entrain provided entertainment on Vineyard Haven waterfront. — Louisa Gould

Lisa Stout, skipper of Isabella, a 21-foot Gannon and Benjamin custom-built gaff rig, and husband John were first-timers in the Vineyard Cup, although they take part in the biweekly Holmes Hole races every summer. Isabella placed first in the small classic boats division, and was just seconds behind Shell Bell, an 18-foot catboat owned by Cheryl and Peter Wildermuth of West Dennis (the catboats and small classics were sailing the same course despite being in two different divisions).

“We were absolutely neck and neck the whole rest of the way in,” she said. “It was amazing.”

The whole weekend is “just a huge effort,” Mrs. Stout said, “And a very successful one, I think.”

“A good time was had by all,” Mr. Callen said, noting that he already has the dates in place for next year’s Vineyard Cup.

Mariners, mark your calendars for July 12 through 14, 2013.