Reach for the stars at Possible Dreams auction August 1

The Possible Dreams auction has raised more than $8,000,000 for Martha's Vineyard Community Services. — Photo by Tim Johnson

A beloved Martha’s Vineyard summer event, the annual Possible Dreams Auction takes place on the evening of Monday, August 1 at scenic Ocean Park in Oak Bluffs.

The event benefits Martha’s Vineyard Community Services (MVCS) and highlights many of the qualities that people identify with the Island experience — a spirit of philanthropy, a broad mix of seasonal and year-round residents, and opportunities to endulge in a “possible dream.”

When it began in 1979, with auctioneer and summer resident Doug Garron, the Possible Dreams Auction was truly a one-of-a-kind event. One of the first celebrity concept auctions, the event is built around the sale of “possible dreams,” opportunities that one would not find on any shelf.

The dreams come in all shapes and sizes and sell for a variety of amounts. Many have a unique Vineyard celebrity quality. For example, in 2005 a sail with Walter Cronkite and Carly Simon sold for $85,000, the single largest bid in auction history.

In a previous piece for The Times, Kate Feiffer wrote, “The Auction’s magic works for one reason: it is a cause that every single participant… strongly believes in.” This support has helped bring in over $8,000,000 for MVCS, all of which has been put towards bettering the lives of the Island’s residents.

This year, MVCS has enlisted the services of professional auctioneer Dan Flynn to keep the auction moving. Joining him at the podium, will be Alex Friedman of Plum TV and Laurel Redington-Whitaker, of WMVY. The two local residents will act as emcees, reinforcing the local connection.

The dream lineup includes a wide assortment of auction items. From a private ice skating lesson with Olympic Silver Medalist Paul Wylie to an all-expenses-paid weekend getaway to Napa Valley, the options are vast and sure to appeal to sports fans, travelers, intellectuals, and everyone in between.

The auction doors open at 4 pm. Bidding begins at 5 pm. A catered dinner follows the auction at 7:30 pm.

The menu includes filet mignon, delectable crab cakes, and a delicious dessert accompanied by musical entertainment by Wes Nagy and Joanne Cassidy.

Possible Dreams Auction & Dinner, Monday, Aug. 1, 5 pm (gates open 4 pm), Ocean Park, Oak Bluffs. Auction tickets only $25; $300 dinner & auction, $2,400 table of 8. 508-696-7900 ext. 267. For more information go to

Maddy Berg, of Annapolis, Md., is a summer intern at The Times.