For years, the Possible Dreams auction has been uniting the Vineyard. Year-round residents and summer visitors, dreamers and donors, come together for a night of philanthropy and possibility.

And this year, the tradition will have a fresh twist, thanks to new members of the committee and Sandy Pimentel, the first-time chairman of the auction. The spirit behind the event — raising money for Martha’s Vineyard Community Services and having fun while doing so — is still there, but for the 34th annual auction, which takes place on Monday, there are slightly fewer dreams, a silent auction, and an after-party.

sandy pimental
Sandy Pimentel, auction organizer. — Ivy Ashe

The auction is usually in the works for about a year, Mrs. Pimentel said. But in March, the committee suddenly found itself without a chairman. Mrs. Pimentel, who was in California with her husband, Paul, who is on the Community Services board of directors, “started calling and saying, what can we do to pull this together?” she recalled. She returned to the Vineyard at the end of March, convened the first committee meeting and became chairman. “The rest is history — here I am,” she said over coffee at Espresso Love in Edgartown this week.

“There’s a lot at stake with this,” she added.

And so Mrs. Pimentel, who has a background in human services and community organizing, and her committee — more than half of whom were new — got to work.

“This Island is really special,” Ms. Pimentel said. “And between my friends and friends of other people who are on the committee, people have really stepped up to the plate. You know, it’s been difficult and hard work, but it’s all been fun for me, I have to say, because of the people . . . and I think the people who have planned this over the years, in the past, have created this legacy for this event.”

While the group has stood by that legacy, there are some clear changes to this year’s format. “We decided in these meetings . . . we needed to make things fresher and new for people,” Mrs. Pimentel said. “We wanted it to continue to be fun; we wanted it to continue to hold the legacy that basically [longtime auction leader] Art Buchwald created . . . he seemed like the kind of guy who wanted this to be an effort that pulled everyone together.

Tyler Alton in the arms of Liz Burnham at Community Services. — Jeanna Shepard

“And so we really made more of an effort to be more accessible to people. And people in the process have sensed that and stepped up to help who would not ordinarily have felt that they could do that.”

This year, Possible Dreams will start with an hour of cocktails and a silent auction, followed by the traditional live auction. Daniel Flynn will serve as auctioneer and Alex Friedman will be the emcee.

The fresh ideas and new people livened up the process, Mrs. Pimentel said, at the same time continuing the tradition of Islanders donating their time and skills. “I think it’s really going to be a great time as a result,” she said. “It’s a lot of people with a lot of great skills who are willing to contribute those skills, who ordinarily would not have been involved, but seemed to be sort of in the spirit of it — they just sort of hopped in, and said, this is great, I can do this.” She credited Marty Homlish and his wife and daughters, who stepped in to help, staff members at Community Services, and longtime volunteers and committee members like Tamara Buchwald for creating positive energy around the event.

“We really have a great auction,” Mrs. Pimentel said. “We’ve got wonderful dreams, we have a lot of great contributions to the silent auction from local vendors.”

lily haynes
Lily Haynes, one of many who benefit. — Jeanna Shepard

Not that it hasn’t been a lot of work. “Logistically, it’s huge,” she said, with tents, permits, tickets, invitations and public relations to handle.

“You have to get people excited enough to talk about it,” she added. “You have to get close to people who are famous, which isn’t always easy.”

But Mrs. Pimentel said the Island is home to people who are willing to give their time, and have done so by donating dreams, including Doug Liman, Henry Louis Gates Jr., Charlayne Hunter-Gault, Jim Belushi, Ted Danson and Mary Steenburgen.

“We’re very lucky to have celebrities on this Island who are very dedicated to Community Services,” she said. “Even though they’re not here for a long time, they are fabulous, they’re wonderful people. We not only have celebrities, we have celebrities that are really wonderful people and that makes a difference.”

And it’s all for a good cause, she emphasized, with 6,000 people a year coming through the programs at Community Services. “That’s a huge number of people for a myriad of services,” she said. “I don’t think people realize . . . but this is a jewel.”

“We’re on an Island. We don’t have anybody around us. It’s us. We’re it,” she said. “And we provide services to everyone, regardless of whether or not they can pay for it. And that’s what this auction does. And the summer people here are as committed as the people who come in the winter, in many ways.”

The event’s sponsors also make it happen: Hewlett-Packard, a new sponsor, has stepped up to the plate, as have Comcast, the Edgartown National Bank and Martha’s Vineyard Savings Bank.

And like every year, the dreams live on. This year, 35 dreams up for bid will take winning bidders from Lake Como or a villa in Abruzzi to the Emmy Awards in Los Angeles, to dinner with stars and the golf course with politicos.

judy thomas
Danika Peters on lap of Community Services child care coordinator Judy Thomas. — Jeanna Shepard

Then there’s this mysterious dream: a trip with Trip Barnes. The many (there could be between five and 50, Ms. Pimentel said) winners of this dream will be treated to a once-in-a-lifetime adventure and “visit places on the Island they’ve never been to see things they’ve never seen,” with this cryptic addendum: interesting refreshments included.

As of now, only Mr. Barnes and Mrs. Pimentel know the details of this dream.

Other Vineyarders have donated their time and talents: one dream offers up dinner with Rose Styron and Henry and Joan Kriegstein, and Clifford the Big Red Dog creator Norman Bridwell is donating a Clifford painting. Chef Christian Thornton will invite one winner into his kitchen, Livingson Taylor will perform a private mini-concert (at a private party created by Elizabeth Eisenhauer), former Navy seal Tom Rancich will join a winner for dinner and a movie viewing, and archeologist Duncan Caldwell will lead a lucky winner on a tour of secret art caves near Paris.

Several dreams will appeal to golfers, from rounds of golf on-Island to trips to Pebble Beach. Others are tailor-made for baseball fans: catching a Red Sox game in the owner’s suite with Alan Dershowitz and David Ginsberg, the team vice chairman, or two tickets to a Red Sox-Yankees game at Yankee Stadium, complete with field access. Two jerseys are available — from the team of your choice.

There’s a one-of-a-kind sculpture by Tony Holand or a limited edition set of two hand-carved scrimshaw wristwatches (the only two ever made) created by the late Tom DeMont.

Bidders can have sushi with Mr. Belushi and have their DNA analyzed with Mr. Gates Jr., win a trip to the Emmy awards or a jaunt to Los Angeles for a day-long recording session with producer and songwriter Bob Marlette,

Next summer, six people will be guests of Mr. Danson and Ms. Steenburgen as they perform the play Love Letters at the Vineyard Playhouse, followed by drinks and light appetizers with the couple. One dream will take the winner and friend to the London set of Mr. Liman’s film All You Need Is Kill starring Tom Cruise and Emily Blunt.

“We want it to be a party, we want it to be fun, we want it to be a party for people of all ages,” Mrs. Pimentel said. “We want to celebrate the fact that we’ve all come together for this event to make it successful.

“It’s quite different, but the essence will be the same.”


The 2012 Possible Dreams auction takes place Monday, August 6 at Ocean Park in Oak Bluffs. Gates open at 3:45 p.m.; the bar and silent auction will start at 4 p.m. The live auction begins at 5 p.m., and an after-party at Hooked begins at 7:30 p.m. Tickets to both events are available at or directly at Martha’s Vineyard Community Services. For more information call 508-693-7900 extension 229.