New races and new venues highlight the upcoming summer of competitive sailing on Martha’s Vineyard, as the crews of weekend knockabouts, family cruisers and high-tech racing sleds gear up for the season.

The Holmes Hole Sailing Association officially got underway on June 21, with 15 boats making the line under light winds on gorgeous evening for the first contest of the season.

The Brenta 38 Starfish, entered by Sail Martha’s Vineyard, won the A division, while Tamu, an Alerion 28 skippered by Tom Wescott, took the honors in the B division.

Holmes Hole hosts fun oriented racing on Thursday evenings and Sundays out of Vineyard Haven Harbor.

Rounding East Chop. — Mark Alan Lovewell

“Another great summer I hope,” said Holmes Hole commodore Mo Flam. “We have about five new boats joining the fleet. I think of Holmes Hole as kind of like the co-op of sailboat racing. Everybody participates. Everybody pitches in and does a little bit, and it gets done.”

Hands down the most dedicated volunteer is Roger Becker, who maintains a complex and labor intensive system of handicapping to keep racing competitive. “He’s the wizard of handicaps,” Mr. Flam said. “You can show up with a million dollar boat, or a boat you just picked up for free. After awhile you’re going to be equalized by his handicap. It keeps everybody interested. Everybody has a chance at Holmes Hole.”

The Holmes Hole Sailing Association caps the season each year with the Moffett Cup, scheduled this year for Saturday, Sept. 8.

Sail Martha’s Vineyard has a few changes planned for the Vineyard Cup, scheduled for Thursday July 12 through Sunday, July 15, including a new venue for the after-race parties.

The event gets underway with Vineyard Cup opening night, formerly named the Sail MV buffet and auction, under a big tent at the Packer yard on Beach Road.

“The idea is to make the whole thing more of a rounded event, rather than being two separate events,” said Andrew Nutton, director of programs for Sail MV. “The board thought it was a good idea to link them together to give a bit of continuity through the four days.”

Vineyard Cup gets underway July 12-15. — Mark Alan Lovewell

The regatta gets underway Friday afternoon, with the first of three days of racing.

A welcome addition to this year’s fleet is the Martha’s Vineyard Regional High School sailing team.

There are already 39 boats signed up to compete.

“We’re looking forward to seeing some new boats,” Mr. Nutton said. “We’re slightly ahead on entries. We’re well on line for a really good year.”

Following each day’s race, sailors will gather at the Martha’s Vineyard Shipyard for socializing and awards. The parties will take place inside one of the shipyard’s enormous boat sheds on Beach Road.

The Edgartown Yacht Club has a busy season of sailing activity planned. In addition to the annual regatta for several one-design classes on July 12-14, the club will stage its Race Weekend July 18-21. The Round the Buoy races are scheduled for Thursday, July 19 and Friday, July 20.

This year’s Round the Island race is Saturday, July 21. There will be a new event for this year’s Race Weekend, for sailors not quite ready to tackle the Round the Island event.

On the same day, the club will stage a 20-mile race called Round the Sound.

Sweet schooner Alabama, where the skies are so blue. — Mark Alan Lovewell

“We’re going to send them across the Chops and down into Vineyard Sound a little bit and turn around and come back,” said Edgartown Yacht Club manager Bill Roman. “It’s an alternative for people who don’t want to do the entire circumnavigation of the Island. They can have a long race, but not have to slog around the 50-plus miles.”

Other notable events this summer from the Edgartown Yacht Club include the annual 12-metre regatta. Mr. Roman expects a few more boats competing this summer than last summer, because the race is being billed as the first in a series of regattas called Road to the World Championships. The 12-metre world championships are scheduled for Newport in the summer of 2019.

“There are a lot of boats being refurbished, refreshed, pulled out of mothballs to compete, ramp up to the World Championships,” Mr. Roman said. “We’re seeing a resurgence in the class. We’ll see probably nine or ten boats here this year, and next year, quite a bit more because we’ll see a lot of boats from Europe coming over. It’s pretty exciting.”

Rounding out the late summer calender will be the Herreshoff 12 1/2 championships. While it’s not officially a national championship, nearly all of the classic fleet is located on the Vineyard, Cape Cod, Buzzards Bay and Long Island. An expected fleet of 25 to 30 of the best Herreshoff sailors are expected to compete for the title on Nantucket Sound August 17 and 18.

On Sept. 5-8, the best Shields sailors in the country will converge on the Edgartown Yacht Club to compete in the Shields National Championships. The 30-foot one-design class is among the most competitive in the country.

“Chicago’s got a big fleet, Newport has a huge fleet, Marion, Beverly Yacht Club, they’ve got a fleet,” Mr. Roman said.

Representatives of most of those fleets, as well as competitors from Texas, are expected to compete.