Guests were shepherded to the Winnetu Oceanside Resort in Edgartown Sunday afternoon for the 37th annual Art Buchwald Possible Dreams auction benefiting Martha’s Vineyard Community Services. Twenty-two dreams were auctioned off by host Jimmy Tingle, including a set visit to Late Night with Seth Meyers, an afternoon with Island artist Allen Whiting, and two vacations in a private home in Galway Bay, Ireland, which raised $24,000, this year’s live auction record.

Norman Bridwell's wife Norma Bridwell and son Tim Bridwell, seated behind Allen and Lynne Whiting. — Mark Lovewell

The event raised more than $400,000 thus far, said Liza May, the auction chairman. Money is still coming in though, she added, and they expect to reach this year’s goal of raising between $450,00 to $475,000.

This year’s event was a tribute to the late Norman Bridwell, the creator of the Clifford the Big Red Dog books and a longtime Possible Dreams supporter.

“We tell our son we’re going to get auctioned off,” said Tony Horwitz, who with his wife Geraldine Brooks were auctioned off as passengers aboard a boat ride to Nantucket on the DiDay. The boat itself, along with the crew, was donated anonymously. “It’s a little mortifying sitting there while people are bidding on you,” said Mr. Horwitz of the event, to which he and Ms. Brooks have traditionally donated.

Top live auction item was a trip to Ireland, which fetched $24,000. — Mark Lovewell

The Sail to Nantucket with Mr. Horwitz and Ms. Brooks sold for $12,000. Bidding quickly rose to $9,000, at which point Ms. Brooks increased the item’s value: she threw in a signed edition of Mr. Horwitz’s Midnight Rising and an advance copy of her latest novel, The Secret Chord, to be released in October.

Humorist Art Buchwald helmed the Possible Dreams auction for more than 20 years. “This was his heart and soul,” said his daughter in law, Tamara Buchwald, who attends every year with her family in her father in law’s honor. “He and all his friends got together before fundraisers were fundraisers and raised money to support everything on the Island that is important,” she said.

The dreams featured at the event began as items that cannot otherwise be bought, and have remained as such.

Ray LaPorte, whose wife Bernadette is director and administration of finance for Martha’s Vineyard Community Services has attended the auction for 29 years. “We have had some fabulous dreams over the years. Years ago we flew with who was then Superman. My son sat as copilot in Christopher Reeve’s twin engine plane and it was a magical day,” said Mr. LaPorte.

Community services executive director Juliette Fay. — Mark Lovewell

“Another one of my favorites was back in 1988. For a hundred bucks I got to DJ at MVY. I played 20 of my favorite songs and that was great,” he said.

Sally Taylor performed original music and added to the evening’s entertainment. Besides the live auction, the event featured a silent auction, a super silent auction, and a raffle.

Mr. Horwitz and director Doug Liman each bought seats at the table of a professional poker game for $500.

“Think of the $500 not as a contribution but as an investment,” said Mr. Tingle. “If you win you get $7,000.”

Mr. Tingle’s lighthearted humor was tempered by more serious pronouncements of gratitude for supporting Martha’s Vineyard Community Services. Money raised will be put toward a variety of programs, including job skills training courses, substance abuse or addiction recovery support, counseling, infant care and more.