Martha’s Vineyard Preservation Trust executive director Chris Scott stood in his usual spot onstage with auctioneer Trip Barnes Saturday night, as Mr. Barnes kicked off the Taste of the Vineyard gala auction. With only five items up for bid, it was a light year for the trust. Bidders generally have some two dozen items to choose from.

But Mr. Scott remained hopeful as Mr. Barnes opened bidding for a Ray Ellis original titled Silver Moon Rising. The artist’s paintings are always a crowd favorite at the auction, and two years ago, Mr. Ellis’s donation had fetched a $65,000 bid, the highest in the history of the auction.

Little did Mr. Scott know, Mr. Ellis and the trust were about to make history all over again.

The number of bidders fell to two after the bidding surpassed market value for the painting. “Then it became very apparent that there were two people, on opposite sides of the tent, who were very focused on it,” said Mr. Scott.

And a bidding war began.

“I’ve been doing enough of these that I can get a sense, when some bidding is going on, about how much momentum it might have. You look in people’s eyes and you can tell if they’re very serious,” said Mr. Scott. “These two had what I call gunslinger eyes, both of them. They were just absolutely focused.”

The two bidders were Scott Earl, of Vineyard Haven and upstate New York, and Pat Morgan, a regular summer visitor to the Island. They happened to be the same two bidders that drove the price up to $65,000 for a Ray Ellis painting two years earlier.

“I thought, ‘Well, this is promising,’” said Mr. Scott as the price continued its upward climb. “After awhile I said, ‘I think this is going to go to $100,000,’ and it did. And it just kept going.”

And going, and going. Before long, the two bidders grew impatient with the modest bid increases of $5,000, and began to throw out increases of $20,000 or higher. As the bids passed $200,000, Mr. Scott began to think of unpaid bills at the trust, which is dedicated to the preservation of historic buildings for active use, and owns such Island landmarks as the Flying Horses in Oak Bluffs and Alley’s General Store in West Tisbury.

“I’m thinking about all the obligations that we’ve got out there. These promises that we’ve made,” he said.

He breathed a sigh of relief as the fear of a potentially unsuccessful Taste of the Vineyard year passed him by. And the auctioneer named Mr. Earl the winner of Mr. Ellis’s moonscape painting, for a final price tag of $250,000, by far the largest single bid ever seen at a charity auction on the Island.

The tent erupted with excitement. “Everybody was shocked and thrilled. People were getting up and yelling. You don’t usually have that at one of these auctions,” said Mr. Scott.

It was a crowning moment for Mr. Ellis, who received a roaring round of applause from the audience once the auction closed.

And history was made.

In 1997, individual lunches with late Washington Post publisher Katharine Graham sold for a total of $100,000 at Martha’s Vineyard Community Services’ Possible Dreams auction, and at the same event four years earlier, two separate bidders paid $81,000 apiece for private Carly Simon concerts in their homes. And in 1988, Ms. Simon agreed to a song and a peanut butter and jelly sandwich with two different bidders for $26,000 apiece. None came close to Mr. Earl’s bid on Saturday night for the Ellis painting.

Perhaps it was fitting, since Ms. Morgan won the bidding war two years ago. Mr. Earl already owns a couple of Ellis paintings, but he said he knew instantly that Silver Moon Rising was special. “When I saw the piece I thought it was really beautiful,” he said yesterday. “I knew that it would bring at least $100,000.”

But he said he didn’t know that he would be the winning bidder. And as the auction progressed, his appreciation for the trust, and his deep admiration for Mr. Ellis took over. “I definitely know that the money went for a good cause. The donation was 50 per cent for the trust and 50 per cent in honor of Ray Ellis,” said Mr. Earl. “Mr. Ellis gives from his heart. In his work you can see. He donates regularly to the organizations on the Island and it’s pretty simple to see that he’s passionate about his work. When he paints, a piece of him goes with each painting.”

Mr. Earl said he plans to mount his new moonscape in his new boat, which he’s named Sandy’s Oldest Sun.

The high price tag for the painting pushed the total proceeds from the two-day, 25th annual Taste of the Vineyard event up to some $400,000. The Taste, as it has become known, kicked off Thursday with the popular gourmet stroll, which drew 750 guests to sample finger foods, beers and wines, and elegant desserts from 75 Vineyard vendors. Perhaps it was the sign of a good year that tickets were sold out three weeks before the event — earlier than in previous years. But the dinner dance and gala auction held two nights later is where the magic really happened. With the help of trust president Bob Cox and vice president of special events for the trust, Nancy Caraboolad, Mr. Scott said the organization designed the event around a sit-down dinner, music from a New York orchestra, and of course, the live auction.

The item list was diverse, if small, and included rental rights to a private parking space in Edgartown, tickets to a New Orleans-themed Preservation Trust party this summer, and a his-and-hers handbag and wine cooler set.

And then there was the painting.

Mr. Scott said the two final bidders were gracious as Mr. Barnes gaveled the item sold, and while Mr. Earl came out the winner, Ms. Morgan did not leave empty handed. At $8,000, she placed the high bid for a catered Fourth of July cookout with friends at the Norton boathouse, near Memorial Wharf, which comes with a front-seat view of the Fourth of July fireworks over the Edgartown harbor.

Days later, Mr. Scott was still recovering from the shock of the Saturday night auction, and reliving the moment.

“I knew we were in a very rare moment, and I think a lot of people in the tent did,” he said.

“I’d like to believe that this is a harbinger of better times ahead for the nonprofit community on the Island.”