The 30th annual George Moffett Race will have more than one winner. Organizers of this year’s contest, scheduled for tomorrow, hope all the sailors who participate will walk away from the contest with smiles.

The Moffett Race is that kind of event. It has always been a contest involving a lot of sailing skill and the fellowship of a lot of champions. That’s not too bad for an event that costs only $40 to enter.

As many as 60 sailboats are expected to start. They are of all sizes. Race chairman Harry Duane of Vineyard Haven said he is expecting that at least 57 boats will be registered for the race and at least three boats will show up just to sail because they failed to register in time.

The boats will gather outside of Vineyard Haven harbor to position for two division starts. There is a starting gun at 11 a.m. and a second start at 11:15 a.m. The best view is from any of the beaches along East Chop. Because this year’s starting line is a good deal farther out, the East Chop Lighthouse may offer the best view from shore.

Part of the impetus of moving the starting line is to insure that boats competing in the race stay away from the West Chop side, where ferries come and go.

The Moffett Race is an end-of-summer sailing ritual. Any event that lasts 30 years on the Vineyard is a big deal and the sailors who participate tomorrow will feel the glow.

“It was conceived by Pat West and George Moffett more than 30 years ago,” Mr. Duane said. “These guys had a really good view of what would be great fun for sailors in the harbor. They also started the Holmes Hole Sailing Association more than 30 years ago.”

Nat Benjamin, a wooden boat builder in Vineyard Haven, said: “To me the Moffett is still a great way to pay tribute to George Moffett, a wonderful friend and a terrific Island philanthropist, who among many credits created Felix Neck Wildlife Sanctuary. He was a great person who loved fun competition, whether it was racing sailboats or cars.”

The race itself is unlike any other on the Vineyard, though it has some similarity to the Opera House Cup race on Nantucket and the Figawi race between Hyannis and Nantucket.

“There are just all types of boats in the race,” Mr. Benjamin said. “It is the rainbow coalition of yachting. You’ve got every shape, size and boat kind participating in the race.”

Boats can be any length as long as they are between 16 and 75 feet. With such a varied size, the boats compete against each other based on a handicap system that was derived years ago.

Because some boats are designed to go faster than others, the system levels the playing field so that it is one sailor against another. And part of the success of the race is that it has been amended through the years to make it better.

“Last year we rewrote the sailing instructions to exactly conform to the United States Sailing Association,” Mr. Duane said. “To win you have to have a good combination of luck and the ability to make critical decisions.”

The race committee has four race courses from which to choose. Depending on weather, current and conditions, the chosen course could be mostly in Nantucket Sound or Vineyard Sound.

Of those four choices, the length of the race might be 10 nautical miles long or 20. Whatever the choice, the race usually fills the afternoon.

Mr. Duane has the distinction of having won the race twice in a 27-foot Soling sailboat called Andiamo II, first in 1995 and then three years later.

“Winning is the greatest feeling. It even compares to winning the seasoned races with the Holmes Hole Sailing Association. If you win the Moffett Race, you are listed there in history. You feel good all year round. I have known sailors who have won and it is the same. It is one of the greatest things to happen in local sailing.”

A lot of skilled sailors have not won, though they try year after year.

Mr. Benjamin is not listed as a winner, though in many other ways he is a winner. His friends and customers participate in the race. In some years, as many as half a dozen boats he has built have participated in the Moffett Race.

Mr. Benjamin and his boat building partner Ross Gannon, another Moffett race sailor, have filled the Vineyard Haven waterfront with quite a few wooden sailing boats.

Roger Becker of Chappaquiddick, a past commodore of the Holmes Hole Sailing Association, has sailed the race for years but never won.

“Thirty years?” he mused. “That means I have not won in 27 years.

“I think this year will be perfect,” said Mr. Becker, who sails a 24-foot red-hulled sloop named Gloria. “There will be great weather. For me it means the end of the season, the big finale for sailing, though there will be sailboat racing through September into October.

“I haven’t won, but I keep trying. I have great faith that everything will fall into place — this year,” Mr. Becker said.