Somewhere over the rainbow, or perhaps somewhere on a small Island nestled into the Atlantic Ocean a few short miles from the Massachusetts coast, dreams really do come true.

The Island’s teenage singing prodigy Katie Mayhew opened the 31st annual Possible Dreams auction last night, held in Ocean Park in Oak Bluffs for the first time, with a powerful rendition of the wistful Wizard of Oz theme song. Rick Lee and Susan Klein returned as auctioneers, announcing the dedication of this year’s auction to one of the events most faithful supporters: the late Walter Cronkite.

In the end the auction brought in close to $500,000; a final tally will be completed in the days ahead.

And while it may have been less than organizers had hoped for, consider this: An invitation to the highest bidder to join Walter Cronkite for an afternoon sail on his personal boat brought in just over $100 in 1979, the auction’s first year. That sail continued to be one of the most sought-after dreams for years afterwards, and Mr. Cronkite’s decades of involvement in the auction demonstrated his steadfast support for Martha’s Vineyard Community Services, the organization that the auction benefits. Last night Mr. Lee read a letter sent by Mr. Cronkite’s daughter thanking the auction committee for remembering her father. “Reach deep and bid high,” she asked of the audience.

Community Services executive director Julia Burgess stood to speak about the agency’s pressing need. “For nearly 50 years Community Services has been the Island safety net,” she said. “Because of the economy, the demand is getting greater . . . . We hope you bid often and high for Community Services.”

The bidding opened with a new feature, called a lightning round. The idea was to sprinkle some more affordable dream options in with high-end prizes. “This is going to go really fast,” warned Mr. Lee as he rattled off a series of Island-themed excursions including a tour of Felix Neck Wildlife Sanctuary, a spot as judge in an Agricultural Fair baking contest, and a spot for one lucky dog in the Island pet parade.

The lightning auctions popped up throughout the regular auction schedule to boost excitement in the crowd. One enthusiastic attendee stepped at the last minute to contribute a kid’s clamming session, which sold for $900.

The spirited crowd cried out in protest when they felt that Mr. Lee closed an auction too early. “I’ve got the last word,” he joked, which stirred a playful booing from the crowd. “What did I say?” he replied, shooting an innocent glance at his co-auctioneer. Guests quickly forgot their annoyance when the auctioneers announced a cocktail and dinner cruise dream aboard Nancy and Chuck Parrish’s yacht Freedom. The catered boat cruise for up to 30 guests under the August 21 Oak Bluffs fireworks brought in $13,000.

Carly Simon was scheduled to make a reappearance at this year’s auction, but had to cancel due to illness. Instead, she attended via cell phone. Ms. Klein fumbled to operate the speaker phone function, to no avail. Finally, she relayed Ms. Simon’s message herself. The message was an improvised song apologizing for her absence. “I’m coming home,” she said finally, “and it feels like I’ve never been gone.”

Ms. Simon’s dream for sale was a sailing serenade with her and her son, Ben Taylor, aboard the schooner Charlotte. Capt. Nat Benjamin will command the sail, which will be catered by Blue Canoe and photographed by Alison Shaw. The dream sold for $10,000.

“I am hugely looking forward to it,” said auction winner Carol Guthrie after the event. “I love Carly. I’ve loved her for so many years, and I love Ben. I always go to see him when he’s playing in Vineyard Haven, whenever I can, so I’m looking forward to this.”

This will be Mrs. Guthrie’s second year winning a dream with Carly Simon. Several years ago, the singer and late Possible Dreams auctioneer Art Buchwald visited her home. Ms. Simon played a song that she had written at Mr. Buchwald’s request for his memorial service, called Too Soon to Say Goodbye. “It’s a really special thing for me to think that I get to hear her sing again because I love her voice and I love her music,” said Mrs. Guthrie.

Marty Homlish and SAP stayed true to form this year with their Ultimate Grand Prix Formula One dream. The winners get an exclusive trip to the Brazilian Grand Prix in Sao Paolo. As Mr. Lee tried to drive the bidding over $10,000, Mr. Homlish stepped in to up the ante, offering a behind-the-scenes visit to the race garage to meet driver Lewis Hamilton, and a signed and personalized Hamilton helmet to any bidder willing to pay $12,000. The final price only hit $11,000, but Mr. Homlish persisted. He offered the second highest bidders, Steve Schwab and John Early, the chance to see the Grand Prix in the location of their choice if they were willing to match the $11,000.

“We said Istanbul, Turkey,” said Mr. Schwab after the auction. “So we’re going to Turkey next June. It will be their third Grand Prix event. In previous years, they won trips to Barcelona and to Brazil. “We didn’t want to go to Brazil again,” said Mr. Schwab. “I knew they built a new track [in Istanbul], so this is kind of a new venue for the Formula One circuit . . . We wanted to go some place really exotic, and Kuala Lumpur was too far. That was an option [too],” he said.

Auction committee chairman Jim Shane was quick to praise Mr. Homlish after the event. “That was a $22,000 dream,” he said of the final outcome.

And while the evening fell short of expectations for total fund-raising, Mr. Shane and cochairman DiAnn Ray said they were pleased. “I think everyone was pleased. Our new venue really worked out,” said Mrs. Ray. “We’ve got nothing but good karma and good feedback from being in this spot. The day couldn’t have been more perfect.”

Mr. Shane said he was pleased to see new faces bidding on dream this year. “We need to move on to the next generation. New blood. New people who get excited and enthused about the auction in the future. This was a building year, and we turned the corner,” he said.