Stars and other well-heeled summer residents can send the population soaring past the 100,000 mark. Offseason, the island's six towns — Edgartown, West Tisbury, Tisbury, Aquinnah, Chilmark and Oak Bluffs — have 15,000 year-round residents, who include farmers, fishermen, artists, writers and descendents of early settlers. Most everyone you meet is interesting: Volker Kaempfert, the muscular co-owner of The Farmhouse B&B who serves you coffee, for instance, once guarded three secretaries-general of the United Nations.
In her weathered, shingled home called Cleaveland House, white-haired, 13th-generation Vineyard resident Cynthia Riggs writes mysteries and rents rooms to authors and artists. She shows a visitor the wooden crib fashioned by sailors on her great-grandfather's ship to cradle the children his teen bride bore and raised on long voyages. With carved posts and a sailcloth bottom, it's open on the side where it attached to the captain's bunk.
Riggs enjoys living "up island" in West Tisbury, away from the store-lined streets of Edgartown, Vineyard Haven and Oak Bluffs. You probably won't see her at celebrity-studded events such as the annual Possible Dreams charity auction, where you bid on a boat ride with serenade from resident Carly Simon ($10,000 this year) or a round of golf with Clinton and pal Vernon Jordan ($2,250).
Each Vineyard town has a personality. West Tisbury is farming country. Oak Bluffs is a more boisterous former Methodist summer camp whose bright-hued Victorian "gingerbread cottages" — as well as its bars — are tourist draws. Oak Bluffs also is one of the oldest African-American vacation destinations in the USA. Obama has visited it before.
Edgartown is filled with the stately white-clapboard former homes of sea captains, upscale restaurants and boutiques. It was a filming site for the movie Jaws and adjoins Chappaquiddick Island (locally called "Chappy"), where Sen. Ted Kennedy drove a car off its bridge in 1969, resulting in the death of a campaign worker. Edgartown and Oak Bluffs are the only towns with bars.
Vineyard Haven, part of Tisbury, has a harbor with hundreds of sailboats bobbing at anchor.
"Up island" towns are on the island's less-populated west side. Chilmark — where Obama is bound — hosts Gyllenhaal's family. Rich residents live behind hedges at the end of long driveways. Westernmost Aquinnah, formerly known as Gay Head, is home to the Wampanoag Indians, spectacular cliffs and a clothing-optional beach. Juli Vanderhoop hosts pizza fests Wednesday nights at her Orange Peel Bakery's outdoor fireplace. Bring $10 and a topping, and join locals for a slice or three.
A tour of the 'real' Vineyard
Tourists spilling off ferries in bustling Vineyard Haven or Oak Bluffs often miss the island's essence, says L.A.-guy-turned-Miami-metals-broker Ross, savoring fresh-caught halibut and Sancerre white wine at Chesca's Restaurant in Edgartown. He offers to give a tour of "the Vineyard most people never see" the next day.
So at 9:50 a.m. on a recent Tuesday, Ross, towheaded son Lucas, 2, and former father-in-law Bill Coleman, 66, await on the porch of Alley's General Store, an island meeting place that stocks everything from old-fashioned penny candy to fishhooks. Coleman, a professor at the University of North Carolina-Chapel Hill, proffers a cup of Alley's perfect coffee, and the tour begins.