What happens to a dream deferred? Fortunately for the bidders and dreamers at the 33rd annual Possible Dreams auction last night, they’ll never have to know.

Beneath the canopy of a beautiful sunset in Oak Bluffs, the audience rallied to raise over $251,350 before the final tally for Martha’s Vineyard Community Services despite the troubled economic times.

This year, the Possible Dreams auction brought in a professional auctioneer for the first time. Dan Flynn of Quincy immediately upped the energy of the buzzing crowd. Right out of the gate, bids, jokes and gratitude stampeded off Mr. Flynn’s tongue, creating a thunderous roll of grands, thousands and “going onces.” Each bid became a hoofbeat in a breathless parade to gather funds for Community Services, which is celebrating its 50th anniversary this year.

Wiet Bacheller, auction cochairman and president of the Community Services board, was thrilled about this year’s turnout. “I’m especially grateful to all of the donors. The variety of dreams is a whole dream in itself. It’s the most varied, and the most exciting lineup of dreams we’ve ever had,” she said.

“It’s such a gift, to get this spirit and this energy and to see all of the people.”

Laurel Redington of radio station WMVY and Alex Friedman of PlumTV were the emcees, making each dream sound more appealing than the last. In a tribute to the longtime host and champion of the Possible Dreams auction, the late Art Buchwald, Ms. Redington began the evening by paraphrasing some of his words. “What really sets this auction apart is that we are bidding on experiences with other people, and that connects us all back into the community,” she said.

The evening began with a series of modest bids, which many remarked was different from years past. “It’s coming back to being something regular people can afford,” said author Geraldine Brooks, who, with her husband, author Tony Horwitz, offered up a dinner in their company. The couple also bid successfully on Kayak While They Work, in which the crew from Vista Window Cleaning and Painting Services washes your windows while you go kayaking with the company’s owner, and the Pajama Pizza Party for 10 kids at the West Tisbury Public Library in the company of Kate Feiffer, Holly Nadler and Margot Datz.

The most exciting moment of the evening came at the halfway point. Before that the bidding had moved slowly, and the tally had come in at around $98,000. Then everything changed. A dramatic bidding war broke out over the dream, Attention from the Flight Deck, which offered the winner the opportunity to fly out from John Wayne Airport to land on the deck of the aircraft carrier, the USS Kennedy. The number climbed up past the $20,000 mark, and had reached $24,000 when a man approached the auctioneer. Mr. Flynn delivered his message to the crowd: Both bidders would get to live the dream if each contributed $25,000. The bidders, Peter Norton and John Noon, agreed; the crowd erupted in uproarious applause.

After that, the night took flight. “You need to have competition between more than one bidder to get everyone interested in the auction,” said auction cochairman DiAnn Ray. “But I do think the auctioneer is syncing with the audience.”

Tamara Buchwald, Art Buchwald’s daughter in law, agreed. “Art really would have loved him,” she said.

The most surprising moment was the lightning round, which offered up several dreams, each to be bid on within a one-minute time limit. “The initial idea was to put items in the program that people who couldn’t afford the big-ticket dreams could get,” Mrs. Ray said. “But then, I heard one item go for $2,700!”

Another big battle came for How Sweet It Is, surely a dream for many on the Island. This one offered a trip to Tanglewood to watch a performance by James Taylor, followed by dinner backstage with Mr. Taylor and his family. Bidding drove the price up to $15,500 where it ultimately came to rest.

Mary Jones, who was visiting from Greensboro, N.C., was hoping for the Taylor dream but came up short. “James Taylor is a big Chapel Hill guy, and we were hoping we could meet him, because we feel very close to him, and he has a special place in our heart, being from North Carolina. I’m so sad we didn’t get it,” she said, slapping her leg with her paddle in mock anger. “But if we drove up the cost, all the better.”

Her friend, Bert Newsome, also from Greensboro, added a bit of trivia. “The first baby present my parents got when I was born was from James Taylor’s parents, when his father was a doctor at the University of North Carolina,” he said.

Carole Simpson, the former ABC News anchor, and her husband, Jim Marshall, took home a big dream: Climb Your Family Tree, where Henry Louis Gates Jr. traces a family genealogy through generations. “My husband really wanted it,” said Ms. Simpson, “but after awhile, he stopped putting his hand up. I insisted on it. I said, If you want it, you’re going to get it.”

Stephanie Oboler was more successful than Ms. Jones, but noted that the worthiness of the cause drove her enthusiastic bidding. She took home three dreams: Bring Arthur to School, which brings Arthur creator Marc Brown to any school in the country; Every Dog Has His Day, which will promote Ms. Oboler’s dog to grand marshal in the Martha’s Vineyard Dog Parade; and Bon Appetit — Oy Vay!, which brings local produce to table, in a dinner with Joan Nathan and Jan Buhrman.

“It’s a fantastic thing, being here. And it’s so good to be able to give something back, and we feel a responsibility to do that. And the joy is twofold, because now Marc Brown is going to come to the school where my kids used to go. It’s great!” she exclaimed.

At the end of the evening, Meg Mercier offered up a painting she had made throughout the course of the evening. It depicted Ocean Park, in the full glory of its blazing sunset, playing a lively host to the even more spirited auction. “I’ve done this three times, and it’s a great tradition. It’s a nice way to remember the auction, and you couldn’t get a more gorgeous sunset,” she said.

And just like that, the natural wonder of the scene became a dream for some lucky reveler, capturing the sunset in an eternal reverie.