Boats will be charging the line in two divisions of the annual George Moffett race this Saturday starting at 11:10 a.m. This year will be the 40th edition of the race, named after one of the founding members of the sponsoring Holmes Hole Sailing Association.

The preliminary forecast for the race is for mostly clear skies, light air from the north, with seas running two to three feet. But whether the wind blows from the north, south, or not at all, Holmes Hole commodore Mo Flam will use a barometer of success that has little to do with the weather conditions.

“A good time,” Mr. Flam said. “A lot of boats turn out and have good competition, but have a lot of fun. Bring a lot of people out on the water, compete, but have fun at the same time.”

Skipper Stephen Besse is scheduled to compete in his J/120 Aprés, with an outside chance to pull off an unprecedented third consecutive victory. Mr. Besse’s second consecutive victory last year was a feat, because each year the winner is heavily penalized in the handicap system for the following five years. The penalty helps prevent domination by one boat and gives the rest of the fleet a better chance of winning. In the true spirit of the event, Mr. Besse said his stiff handicap should allow someone else to win this year.

“I don’t think it would be good for the event for me to win three years in a row,” Mr. Besse said. “There will be a handicap sufficient that it won’t happen three years in a row. Nevertheless I’ll race and do the best job I can.”

The handicap system is meant to equalize the competition, and it is always put to the test in the Moffett, where vintage schooners compete with high-tech racing sleds, family cruising boats, 19-foot catboats, and everything in between.

“What is most fun about the Moffett is the diversity of boats,” Mr. Flam said. “From Juno and Charlotte, Steve Besse in the J/120. We now have seven Alereons in the fleet, I think all seven are signed up to do the Moffett. It’s a very diverse fleet. We have classic boats, gaff-rigged, schooners, everything.”

Mr. Flam will skipper his Alereon 28 Penelope in the race.

Unlike the summer Holmes Hole races, which are run under complex handicaps based on how the boat and crew performed in previous races, the Moffett is based on standard PHRF rating.

By the time online entries closed on Monday, exactly 40 boats had signed up to compete in the 40th edition of the race. That number is down a bit.

“We’re a little behind years past,” Mr. Flam said. “We’ve had close to 60 boats. I think a lot of people just don’t have time to sail. Part of the idea of Holmes Hole is to encourage everybody to race and participate, but there has been a little shrinkage.”