The Possible Dreams Auction has long been a highlight of the Vineyard summer. The high-stakes bidding contest, attended by both notable auction dream donors and high rollers, always has as much preauction speculation as postgame buzz: Who will be there? What will the top bid be?
Now in its 37th year, this Sunday’s auction promises to be no less exciting than it was in its early days, when the Pulitzer Prizewinning humorist and columnist Art Buchwald recruited his celebrity friends and kept the crowds laughing — and bidding.
Even if you’re not in a position to raise a paddle for a luxury vacation, or the chance to hang with a celebrity, the auction offers a lot of action and entertainment for the reasonable entrance fee of $25.
Under the big tent on the Winnetu Oceanside Resort property, funnyman Jimmy Tingle will once again serve as auctioneer, offering quips along with clever inducements to would-be bidders. His sidekick, Guinevere Cramer, will return to add her effervescence and charm to the mix.
A concert by Island favorite Joanne Cassidy and her band will kick off the night. For the first hour, guests can enjoy the music, mix and mingle, snack on goodies by Vineyard Haute Cuisine, and check out the selection of unique silent-auction items.
Then the real fun begins. Topping the list of celebrity-centered dreams this year is one with comedian Seth Meyers that includes tickets to a taping, a meet-and-greet, and a backstage tour of the Late Night set. Mr. Meyers is married to human rights lawyer Alexi Ashe, whose family has a home in Chilmark. The couple regularly spends time on the Vineyard, so it is a possibility that Mr. Meyers, in the tradition of past Possible Dream donors, will attend the auction.
“You never really know who will turn up,” says auction chair Liza Cowan May. Some of the dream donors are confirmed to be on hand, including Sally Taylor, who has recently dedicated herself to a multidiscipline art project called “Consenses.” Ms. Taylor will lead a workshop for a winning bidder and nine friends, exploring new ways of expression.
Pulitzer Prizewinners and Martha’s Vineyard residents Geraldine Brooks and Tony Horwitz will be at the auction to talk about both of their new books and introduce their auction item. They will accompany the winning bidder and friends on a sail to Nantucket.
Along with the Seth Meyers dream, items expected to attract some heavy bidding are a stay in a private castle-style home in Galway, Ireland, and a Red Sox package that includes two seats in the owner’s suite at Fenway and a Florida spring-training-season getaway package.
Perennial favorites include a private concert with Livingston Taylor, a DNA consultation with Henry Louis “Skip” Gates Jr., and dinner with journalist and civil rights activist (and vintner) Charlayne Hunter Gault.
The Possible Dreams Auction has always been known for the number of illustrious Vineyarders who have donated one-of-a-kind experiences over the years, and for the bidding wars that these items have been known to generate.
This year, Ms. May says, the committee has made an effort to bring some more local flavor back into the event. Some interesting new items include a private catered party at the Ritz with popular local band Johnny Hoy and the Bluefish, and a picnic on the porch at Good Dog Goods with local children’s book authors Kate Feiffer, Marc Brown (the “Arthur” series) and Richard Michelson.
The auction this year is dedicated to Clifford the Big Red Dog creator Norman Bridwell, a longtime summer resident who died in December. For many years, Mr. Bridwell donated a Clifford-themed dream to the auction. “He was not only a beloved writer but an incredible supporter of Community Services and the auction,” says Ms. May.
A couple of new silent-auction items will give guests the opportunity to be a winner without breaking the bank. For $500, you can be one of 14 players in an exclusive game of poker at a private home with, among other poker professionals, ESPN World Series of Poker champ Jesse Sylvia of West Tisbury.
Local artist and muralist Margot Datz has created a special painting of the Vineyard that a lucky ticket holder will get to bring home. There will be 100 $100 tickets sold for a chance to own it. All ticket holders will receive a signed limited-edition print.
“I think we had to think outside the box a little more this year, and come up with some new ideas,” said Ms. May. “We needed to approach the auction in a way that it could be more inclusive.”
The committee is also hoping to attract some new and younger guests. The live-auction list has been pared down to 21 items to keep the action moving along. Ms. May hopes that bringing people like Joanne Cassidy and Sally Taylor on board will add some new vigor to the three-decade-old event.
Most important, Ms. May wants to remind people that every purchase is a donation toward an organization that represents the interests of the Vineyard as a whole.
“I want the auction to be reflective of the the philosophy of Community Services,” she says. Even those who come with no intention to bid can buy a ticket for the raffle (first prize: dinner for two at the Terrace restaurant and an overnight at the Charlotte Inn) and help with the fundraising effort.
This year, according to Ms. May, the auction has managed to gather more sponsors at the $1,000 level and above than ever before. Close to 100 volunteers have been recruited, and a multitude of local businesses and individuals have donated goods and services.
“It really is a community effort,” says Ms. May, “which is appropriate since it’s a fundraiser for Community Services.”
Martha’s Vineyard Community Services (MVCS) provides a wide array of social services for Vineyarders from children and families to seniors, to the disabled, to veterans. Over 6,000 people a year receive help of some sort from MVCS annually.
According to Executive Director Julie Fay, the organization can use every penny these days. MVCS recently added a host of new programs, including a crisis stabilization center, a veterans’ outreach program, and a collaborative initiative designed to address a variety of issues that are increasingly plaguing the Island’s youth population.
“I think that now more than ever, Community Services needs our support,” says Ms. May. “If you can’t go in and spend $5,000 or $10,000, even $100 — or a $10 raffle ticket — will help toward reaching our goal of raising $475,000” (last year’s auction netted $462,000).
Possible Dreams Auction, Sunday July 26, Winnetu Oceanside Resort, Edgartown. Tickets starting at $25, available here.
