Given that my visit to Martha's Vineyard occurred just a few weeks before President Obama’s planned August vacation there, I suppose I was keeping my eye out for things for the Obamas to do. (As if they need my help. The family has often summered there, before and after Obama becoming president.) All right, it’s probably unlikely that the leader of the free world will jump off a bridge—though it would make a superb photo op.
Locals told me that the family keeps a low profile—unlike the previous Democratic president, who, I was told, used to get his ice cream fix at popular Mad Martha’s and tended to wade into the summer crowds. But there was speculation as to whether the Obamas would again stay at the 28-acre Blue Heron Farm, or at some other well-appointed estate.
In any event, here some presidential and non-presidential ways to keep busy—and not so busy—on this enchanting, homespun Massachusetts island.
Jump off a bridge
On Beach Road between Oak Bluffs and Edgartown, you’ll find a wholesome scene out of Norman Rockwell: kids of all ages (but mostly actual kids) taking joyful leaps off a bridge that crosses an inlet between the ocean and a marshy pond. You can go solo, in pairs, in trios—apparently the key is, “Don’t think, just jump.” Then swim or tread the aquamarine waters below before scampering up the smooth rocks to shore. It’s a true Vineyard initiation. I wasn’t man (or kid) enough to take the plunge, so I just took pictures.
Come between 10 and 11 a.m. to witness the meticulous process of crafting fudge at Murdick’s. Owner Michael McCourt has been overseeing the Vineyard’s three shops and the 130-year-old recipes for over 20 years. I watched the team heat the ingredients in copper cauldrons, pour the resulting chocolate liquid onto marble tables, and work the slowly setting concoction into huge, marshmallow-studded loafs. McCourt told me about the time that President Obama’s daughters came in for fudge, and when President Clinton had the shop send fudge to “everyone in town.”
The Vineyard is so friendly and safe that if you’ve ever felt like hitching, or picking up a hitchhiker, now is the time. It's an efficient and social way to get from Edgartown to Oak Bluffs to Vineyard Haven. Ask former hotel pianist Paul Samuel Dolman. He put out his thumb one day and got a ride from a skeptical man who had never picked up a hitchhiker before: Larry David. Dolman chronicled what ensued with the famous curmudgeon in his book Hitchhiking with Larry David. Originally self-published, the memoir proved so marketable that it was picked up by Gotham Books.
Take a historical tour
Edgartown dates from 1642 and contains at least 70 buildings of historical note. The Martha’s Vineyard Historical Society publishes a booklet for self-guided tours; guidebooks like Frommer’s offer an abridged list. I was more spontaneous; I had no plan but paused to note the date plaques on whitewashed structures like the Chappaquiddick House (1819). (Rustic Chappaquiddick island, its name still bathed in Kennedy-era scandal, is accessible via a minutes-long ferry ride from Edgartown.) The Captain Warren House on Water Street (c. 1850) sits like a haunted relic of its former self. A passing local saw my interest and helpfully told me, “It's for sale for $3.5 million.”
Chill out and wander
The Vineyard is the antidote to our wired, virtual society, so force yourself to check out and become analog again. Leave modernity behind on the mainland. Use your feet and just wander off the main streets of the towns. Admire the island’s galleries and public art. Look at ponds, marshes, boats, fishermen.
Reflect, contemplate, appreciate
Find a pocket park or patch of sand and make like this Edgartown sculpture. I have yet to find a more rewarding place to do nothing.