The sailing season is still months away and plans are now under way for the Vineyard Cup, a three-day regatta. Organizers plan a larger and more high profile event, one that is easier to view. Last year the weekend racing attracted more than 80 sailboats and this year the numbers could exceed 100.

Racing takes place Friday, July 16 and runs through Sunday, July 17. Sailboats of all sizes will be competing for prizes and at least one is coming from as far away as Florida.

The event which showcases competitive sailing on the water and fellowship on the shore is now in its fifth year. Brock Callen, regatta chairman, said he is seeing increased support from old friends and is making new ones. They’ve got old sponsors like the Black Dog and Men’s Journal and some new boat manufacturers have stepped in to support the contest.

The racing weekend headquarters will be moved to the center of the town, a tent to be raised at Beach Road Extension, which is next door to the waterfront Black Dog Tavern. Over the last four years, the contest was headquartered at Owen Park.

Beach Road Extension accesses Five Corners and will be more like a walking promenade, Mr. Callen envisions. Banners announcing the sailing weekend will be hung from Main street lamps. Town selectmen have made a commitment to support the event in more ways. Mr. Callen said he has also earned the support of the Martha’s Vineyard Chamber of Commerce.

Last year, the event raised $45,000 for the nonprofit organization Sail Martha’s Vineyard. With more participants and sponsors, Mr. Callen said he thinks they will raise even more.

Sail Martha’s Vineyard is a nonprofit organization committed to providing free sailing instruction to Island children.

Since its inception, thousands of youngsters have gone through the summer programs. Many of the sailors have gone on into competitive sport.

Mr. Callen said 475 youngsters will be enrolled in the organization’s many summer programs. Three hundred of them are from the Island and will be sailing probably for the first time. Sail Martha’s Vineyard uses Sailing Camp Park, which overlooks Lagoon Pond for the bulk of the sailing instruction. Underwriting the cost of these programs is covered by two key fund-raisers, the Vineyard Cup regatta, and a seafood buffet and auction which takes place Saturday, July 9. It is a busy week for the town; the Tisbury Street Fair is Friday, July 8.

There will be plenty of opportunity for nonsailors to enjoy the Vineyard Cup, more than before. Mr. Callen said organizers have shifted the racing closer to Vineyard beaches, making the racing viewable. There will be racing just offshore from the Joseph A. Sylvia State Beach, which runs from Oak Bluffs to Edgartown. The largest sailboat participating, so far, is Juno, a 65-foot schooner built on the Island.

East Chop Lighthouse and the overlook from East Chop Drive provide a panoramic view of some of the racing. Mr. Callen said there is more sensitivity toward improving the views for those who just want to watch and photograph sailboats racing.

There is morning and afternoon racing each of the three days. Mr. Callen said efforts are under way to organize a Saturday morning parade. “After the racing, there is a party,” Mr. Callen said.

The festivities take place at the Beach Road Extension and include plenty to eat and drink. An admission bracelet is $30 a night, or $75 for all three nights. Because of the significant help from sponsors, all the money raised from the sale of bracelets will go to the nonprofit organization, Mr. Callen said.

Sailors and visitors will still use Owen Park as a stepping stone for the start and end of the racing, as it offers public restrooms and showers and plenty of space for dinghies.

In addition, the Sail Martha’s Vineyard crew will host racing in Menemsha Pond on that Saturday, tied specifically to the Vineyard Cup event, though they race weekly throughout the summer.

The Vineyard Cup is not happening in isolation. The Edgartown Yacht Club has two sailing events in early July which will give boaters plenty of reason to be on the water, stay on the water or keep an eye on the water. The ’Round-the-Island race, is on Saturday, July 9. And the club’s 88th annual regatta will coincide with the Vineyard Cup.

Mr. Callen said this year the yacht club and Sail Martha’s Vineyard events do not conflict.

Last year there were 58 cruising and racing class sailboats participating in the Round-the-Island Race, a widely popular contest that like Vineyard Cup attracts sailors from beyond these shores. They race a 52.8 mile course around the Island that takes all day. This year, the race has a new sponsor, Mount Gay Rum. The race was started in 1938.

Mr. Callen said of the ’Round-the-Island race participants, “We hope they’ll stick around and have some more fun,” and participate in Vineyard Cup’s weekend of racing.

Coinciding with the Vineyard Cup, the Edgartown Yacht Club regatta attracts a different kind of sailor. Over 200 boats, all one-design sailboats, will compete in races outside Edgartown harbor. Nearly half of the fleet are eight-foot sailing dinghies captained by experienced youngsters. The boats are called Optimists. The largest sailboats competing in the racing are Shields sailboats with hulls that measure 30 feet.

Information on these sailing weekend events is available at:, and