The Obamas’ Summer Hideaway

As the Obamas depart for Martha’s Vineyard, Stephen L. Carter, a longtime Oak Bluffs vacationer, Yale law professor, and author of Jericho's Fall, on why the Island is the Obamas' best shot at a normal family vacation.

04.08.09 6:10 PM ET

So the president and the first lady and their beautiful first daughters are headed for Martha’s Vineyard this weekend. As a longtime vacationer in Oak Bluffs—a town "down-island" from where the Obamas are renting a place in the "up-island" Chilmark beginning on Sunday—let me say, welcome. Or, rather, welcome back, because the family has been to the island before. The difference is, there was less hoopla then. One of the many aspects of the Vineyard that attracts so many well-to-do families from African America is precisely that: the chance to be lost in the crowd. If you are black, and have money, you are certainly free to spend your time in the Hamptons, or Palm Desert, and everybody will notice you, because your skin color is not the norm. By going instead to the Vineyard, you can hide. On the Bluffs, African America is everywhere.

The Obamas evidently plan to follow the model of generations of middle-class African Americans before them, to relax with their children in an almost magical world where, but for the motorcade and the security guards, the family would blend in perfectly.

Indeed, the only time I ever saw Barack Obama in the flesh—no, we do not all know each other—was in Oak Bluffs, in the summer of 2004, after his electrifying speech at the Democratic National Convention. The Obama family was strolling merrily along the street, the parents lovingly swinging their little girls, nary a reporter or aide or security guard in sight. This year, I am sure, things will be a bit different. When President Clinton used to travel to the Vineyard, the Island’s hotels were scarcely large enough for the entourage; I can only imagine the size of the support staff the president needs today.

President Clinton was much-loved in African America, and so was much welcome on the island. President Obama is, to say the least, lionized in African America, and so the excitement of his visit is greater still. And yet I suspect that the island’s veterans will take it all in stride. The Vineyard has hosted Oprah Winfrey. Spike Lee has a house there, as do, so it sometimes seems, half the black corporate executives in America.

For black Americans, Martha’s Vineyard is a place to blend in; and to be left alone. Celebrities brush shoulders with noisy teens at ice-cream parlors and restaurants. Film stars and CEOs frolic on the same beaches that schoolteachers and small-business owners enjoy. And happy black children are everywhere.

As for me, I first traveled to the island well over 40 years ago, in the early '60s, a time when, as a character in one of my novels puts it, “Martha’s Vineyard, and the black middle-class colony who summers there, was still smart and secret.” The frantic rush through the night to catch the first ferry of the morning, my father bravely at the wheel all the way from Washington to Wood’s Hole, is among my warmest childhood memories.

America is full of black men and women with similar memories; and Oak Bluffs is full of black children for whom the same memory is being made now.

Although the history of African Americans on the Vineyard goes back some 300 years, the great rush that foreshadowed the creation of the black colony began during the Reconstruction years, as former slaves and other freedmen began earning enough money to afford a bit of leisure, but found many of the nation’s resorts still barricaded against them. And so they created their own.

In those days, the Vineyard largely centered around Edgartown, the whaling and fishing village to the south, and the Methodist camp meeting grounds, and assorted hotels, to the north, in what would later become Oak Bluffs. At this time, the black families that flocked to the Vineyard centered around the area known as the Highlands, in what is now East Chop, the priciest part of town (where the Obamas have stayed before).

The Highlands was developed by speculators who believed, in the post-Civil War boom, that the Island’s summer activities, both as a resort and as a site for religious-revival meetings, would spread from the town proper up into the lush hills. The land was bountiful, and the views were beautiful, but the effort failed, and the developers went belly-up. The collapse of the real-estate market in the Highlands might explain why so much of the land was bought by black families: It was cheap.

A couple of years ago, I met a woman whose family integrated a neighborhood of Oak Bluffs that was then all white, and is now nearly all black. The neighborhood borders a park where, decades ago, a playground stood. The woman told me how, once her family moved in, the white parents no longer permitted their children to go to the playground. She and her siblings asked her parents why. “Because they’re so happy to have you here,” said her parents, “that they want you to have the playground all to yourself.”

In a way, the stories adults tell children are not that different from the stories adults tell each other. When my parents first took their five children to the Vineyard, large chunks of Oak Bluffs were a playground that African America had all to itself. When my wife and I visited for the first time a little more than 20 years ago, this was still largely true. The town is far more integrated now: There is no stopping progress. Indeed, an article in the New York Times a few years ago noted that fewer and fewer of the home sales in Oak Bluffs are to black families.

Yet the black middle-class colony, if no longer secret, certainly remains. My wife and I raised our children around trips to the Vineyard—that was what they looked forward to every summer. It did not hold them back in the world, and, in some ways, strengthened them, as if to say, yes, yes, there are others like you—black children from similar backgrounds, and of similar interests. Perhaps, as many believe, the election of Barack Obama means that such distinctions will be less important. Maybe that is our nation’s glowing future.

But, for the moment, the Obamas plan to follow the model of generations of middle-class African Americans before them, to relax with their children in an almost magical world where, but for the motorcade and the security guards, the family would blend in perfectly. We are delighted to have you back, Mr. President, and we’ll pretend not to notice the entourage.

Stephen L. Carter is the William Nelson Cromwell Professor of Law at Yale, where he has taught since 1982. His seven nonfiction books include God’s Name in Vain: The Wrongs and Rights of Religion in Politics and Civility: Manners, Morals, and the Etiquette of Democracy. His first novel, The Emperor of Ocean Park (2002), spent eleven weeks on the New York Times bestseller list. His fourth novel, Jericho’s Fall, will be published in July.