In the third chapter of Vinson Cunningham’s debut novel, Great Expectations, David Hammond finds himself on Martha’s Vineyard, fundraising among friendly wallets vacationing on-island. He is an aide to an unnamed Barack Obama stand-in (“the Senator”) who is campaigning for the 2008 Democratic nomination for president. As Karen Cox, the bundler David is boarding with, counts out sixty thousand dollars in checks — “twice my salary,” he notes — she looks him over approvingly. He’s black like she is, if a bit younger, doing important and prestigious work on behalf of the race. “Are you going to law school?” she asks him later, in a tentative recruitment into her fair-weather community of black elites. “You should,” she advises. “You’ll make some money and you turn up here in the summers.” There’s a path laid out for David if he wants it, and he spends the rest of the book wriggling with whether he truly does. “The whole island was standing at the shore, friendly as Karen Cox in the morning, waiting for your boat to reach the dock,” he thinks, as a campaign event is about to begin.

Oak Bluffs on the Vineyard, where the fundraiser has vowed to bring in two hundred thousand dollars for the Senator, is possibly the most famous of a handful of black resort towns, including Sag Harbor’s SANS (Sag Harbor Hills, Azurest, and Ninevah Beach, in the Hamptons), Idlewild in Michigan, and Highland Beach in Maryland. In the late nineteenth century, a slim column of black people — business owners, doctors, lawyers, and their ilk — became wealthy enough to take long, luxurious vacations, but they soon found their options limited: the Supreme Court dismantled the Civil Rights Act of 1875 eight years after its passage, and established de jure segregation in 1896 via Plessy v. Ferguson. In a sense, the black resort town sought to fulfill that case’s empty promise of “separate but equal” in the realm of leisure, as entrepreneurs saw the black elite’s desire for rest as the business opportunity that it was. Within a few years, hotels, beachfronts, boardwalks, and cabins were all established in spite of segregation and with the promise of liberation not for all, but at least for some, at least for a few months out of the year. 

The Martha’s Vineyard chapter in Great Expectations attaches the novel to a minor canon of books, films, and TV shows that use black resorts to dramatize an ambivalence toward aspiration among the black elite. These days especially, the black resort town seems like it’s everywhere, the setting for escapist beach reads and reality television, as well as more high-minded literary fiction like Cunningham’s. This micro-genre plays out a set of contradictions: between a desire for a specific vision of racial achievement and a sense of that achievement’s limits, between characters’ respect for the histories of their refuges and their uneasiness with the moral ugliness that sustains these enclaves, between a desire to elevate the race and the knowledge of the black masses that must be shunted aside in the process. As displayed in these works, the black resort town embodies a larger dynamic, making clear how the symbols of black ambition — and so-called “black excellence” — can serve to paper over the elite’s indifference to the needs of the many.

In the early twentieth century, black and white hoteliers alike sought to lure black vacationers. Oak Bluffs grew out of a black foothold in old Methodist and Baptist revival grounds, where by the mid-1950s black people were the “ink” of Inkwell Beach. The landmark Shearer Cottage grew from a cozy spot on the island where friends of the Shearer family might come stay to a bona fide destination, where personalities such as the singer Ethel Waters and the politician Adam Clayton Powell Jr. might show up in the guestbook. In Sag Harbor, the black sisters Maude Terry and Amaza Lee Meredith bought up plots of land in 1939 to create a cluster of summer homes. White developers built Idlewild, Michigan to draw summering black midwesterners. After getting turned away from a beach restaurant in Bay Ridge, Maryland, Frederick Douglass’s son Charles bought land on the Chesapeake and eventually incorporated it as the town of Highland Beach. 

That history serves as a backdrop in Toni Morrison’s Love, from 2003. The novel charts the rise and fall of Bill Cosey, who buys a down-on-its-luck whites-only club in 1930 and refurbishes it with the goal of creating a place where black vacationers can enjoy themselves in dignity and comfort. “Flocks of colored people would pay to be in that atmosphere,” Morrison writes. Soon, the crowds throng: “Cosey’s Hotel and Resort was the best and best-known vacation spot for colored folk on the East Coast,” who “all felt a tick of entitlement, of longing turned to belonging in the vicinity of the fabulous, successful resort controlled by one of their own.” Cosey’s resort serves a political function — it “was more than a playground; it was a school and a haven where people debated death in the cities, murder in Mississippi, and what they planned to do about it other than grieve and stare at their children.” One character goes so far as to suggest that Cosey “helped more colored people here than forty years of government programs.”

These Jim Crow resorts didn’t just seek to affirm the humanity of their visitors, but also sought to offer relief from the pressures of life under the color line. As the historian Mark S. Foster has written, during that period “blacks could almost never achieve total relaxation,” but “they came closest to doing so when there were no whites around.” On the surface, a black resort is very similar to a white resort: sea, sand, wine parties on the shore, humble servants bowing and offering up trays of nourishment. That the black resort exists in parallel to its white counterpart is part of its appeal. As the historian Myra B. Young Armstead suggests, the black resort had “a curative power bearing a distinctly ‘race’-free character.”

That sense of relief captured the heart of the Harlem Renaissance writer Dorothy West during girlhood family trips from Boston to Martha’s Vineyard. “I didn’t know that there was winter here,” she tells the camera in Salem Mekuria’s 1991 documentary As I Remember It. “I didn’t know that there was school here. But what I did know was that there was nobody here that called you nigger.” West’s novel The Wedding — published in 1995 and set in the black resort heyday of 1953 — centers on the Coles family, black New Yorkers whose daughter Shelby is preparing to marry a white jazzman. Years before the main action of the novel, when the bride-to-be is a little girl, she gets lost chasing a puppy. Somehow, she finds herself in one of the island’s white communities, “drawn to this sanctuary because it resembled home, with its little park and its children playing and its mothers watching them.” Even as the white families grow increasingly sympathetic toward the colored family struggling to locate their little girl, they overlook the fair-skinned Shelby in their midst because they don’t expect a black child to look so similar to their own. “Those who knew colored people only as servants and veered from thinking of them otherwise could not make any association between the poised and lovely child who had brightened their morning and the colored child who had gone and gotten herself lost,” West writes. Eventually, the whites realize that Shelby is not in fact one of their own, and the police take her home. “It was rare in this bucolic summer resort off the coast of New England to feel a ripple of unease about the color of one’s skin,” West writes. But the mode of Shelby’s return punctures the idyll: “now it was as if a cold wet wind had blown through the community.”

If Shelby’s mistaken sojourn exposes the similarities of the summering classes, a moment from Colson Whitehead’s best-selling 2009 novel Sag Harbor reinforces their differences. Now it’s 1985, but the white and black vacationers are no more integrated than they were in Shelby’s youth. While summering in the Hamptons, the fifteen-year-old Benji Cooper and his friends spy some white wanderers who have strayed too far onto the black side of a beach in SANS. The black teenagers pull out their binoculars because “any infiltration had to be checked out.” But the white couple gets nervous and turns around. “Something was off,” Benji imagines them thinking. “Everyone was brown,” he adds. “Black eyes glared down from the beach houses.” The black resort can function like a fortress. It’s a distant outpost on stolen native land — Benji and his friends spend weeks of their summer misinterpreting “sagaponac,” a word from the Shinnecock people who are otherwise absent from their community, to mean “land of the big brown nuts” instead of “ground nuts” — but it also has a border to be patrolled, watched from both sides.

But it’s not only white people who are kept out. In Love, when local working-class black people seek to enter Cosey’s paradise, they’re deemed unworthy and kept at bay: “Pleasantly. Regretfully. Definitely.” Morrison observes that “it comforts everybody to think of all Negroes as dirt poor, and to regard those who were not, who earned good money and kept it, as some sort of shameful miracle.” Cosey’s little “playground” by the sea is “for folk who felt the way he did, who studied ways to contradict history.” Go-getters. Strivers. Showing Cosey’s resort as a place for the black elite to segregate itself from the masses, Morrison teases out how a vanguard’s prosperity does not materially benefit the collective.

In some cases, that prosperity is gained at the collective’s direct expense. In The Wedding, the Coles family has made its fortune by wringing usurious rents from Harlem’s Great Migrators, and in a moment of acute guilt the slumlord matriarch reflects on her victims: “I spent the day in a nightmare. I watched a parade of dead souls. They had died in my houses,” she says. “But others kept coming up from the South looking to claim their piece of the promised land. My houses stayed full. My profits never fell.” She plowed those profits into a spacious house that anchors the Oval, a group of homes that constitutes an esteemed slice of the black summer society on Martha’s Vineyard.

Still, The Wedding is compelling to some because of its portrayal of what has come to be known as black excellence. As Oprah Winfrey explained when she adapted the book for a TV audience in 1998, she was drawn to The Wedding because “it shows a world that most people have rarely seen, a world where black families are all highly educated” and “very successful.” That world held particular interest for West. She recalled in a 1971 column for the local Vineyard Gazette that her family was part of an initial wave of black vacationers on Martha’s Vineyard. Some of her short stories, collected in 1995 in The Richer, the Poorer, paint the picture of that low-key environment: a little boy tries to find a made-up bird, a woman tries to maintain proprieties as an acquaintance grows increasingly ill. In her essay “The Legend of Oak Bluffs,” also in the collection, West writes that “it was a fine accomplishment for these early comers to the island to own summer cottages, whatever their size, whatever their lack of inside conveniences.” Over time, though, her cohort of coolly Protestant Boston families were joined in Oak Bluffs by the Coles group of flashy, well-to-do black New Yorkers — “achievers,” she called them. “They worked hard and they played hard,” she wrote in the Vineyard Gazette column. The island went from a setting to a scene — one in which not all characters were welcome. In The Wedding, newcomer Lute McNeil can’t break into the ranks of the Oval, where he has managed to rent the home of an ailing resident. Though he has money, the whispers of his déclassé life in Boston — three daughters with three mothers either dead or out of the picture — are enough to throw the Ovalites into a tizzy. They scorn him and thwart his efforts to purchase a house. Even their hired help hesitates to socialize with his. “You can never ever buy background,” Shelby’s mother seethes at Lute in the Oprah adaptation. “You can’t rent breeding.”

Such exclusionary thinking was equally on display in 1999, when Lawrence Otis Graham published the best-selling Our Kind of People, a tell-all guide to the world of the black elite. Graham gleefully uses interviews and memoir to point out the anxieties that build up among the denizens of black resort communities, among them the fear of encroachment of poorly assimilating newcomers. “They think they’re fitting in,” one summerer scoffs at a gaggle of black day-trippers on Martha’s Vineyard, “but they are clearly not our kind of people.” Though the book studies black elites in different settings, its 2021 television adaptation, co-produced by Karin Gist and Lee Daniels, is set just in Oak Bluffs. (In one dramatic scene, the show’s lead is denied admission to a black ladies’ society.)

Two years later, the series was followed by a reality TV show set in the same milieu. Summer House: Martha’s Vineyard has all the hallmarks of both the Bravo reality and black resort microgenres: a facade of polished striving thrown in front of a gurgle of anxious status seeking. When the show’s production staff went to the Oak Bluffs select board to get filming permits for a black spin-off, one black Vineyarder stood up in the meeting and tsk-tsked the idea. “This program is a horrible reflection of Martha’s Vineyard and Oak Bluffs,” she said, according to the Vineyard Gazette. Worried about the types who might be drawn to the island by that reflection, she said, “I am concerned about my property value.” In the show, from the moment the cast arrives on the island, they play into the stereotypes of black resort life that they hope to embody, hyped to take their place among the island’s black upper crust. In one episode, during which the cast visits the Vineyard’s African American Heritage Trail, their guide asks if they’ve read The Wedding. They’re stumped. No one has read it. They haven’t even seen Oprah’s made-for-TV adaptation.

Silas, who works in finance, touts his affiliation with the talented-tenth Alpha Phi Alpha fraternity — W.E.B. Du Bois was an honorary member; Martin Luther King Jr. pledged — as well as his status as half of the cast’s only married couple to establish himself as the leader of the house. But when his wife, Jasmine, who once had to live out of her car, breaks from her dutiful housewife routines by preparing an unsatisfactory breakfast, burning his pants with an iron, and daring to express her discontent, he dangles divorce. He explicitly threatens to withhold the respectability of marriage from her for tarnishing his patriarchal Race Man image. Still, the allure of their lifestyle seems to keep her bought in. “Black excellence is everything,” she says at one point, with great emphasis. “At the end of the day, that’s all I give a fuck about.” What matters to them is the narrative of excellence, with the black resort as a backdrop, and things get nasty when that narrative is interrupted.

The literature of the black resort takes pains to show that the kind of black excellence on offer at such places is stuck in a white supremacist logic. In Love, even the excluded locals take pride in Cosey’s accomplishments, yet, as Morrison shows, integration begins to undo his efforts. By the sixties, when the whites-only hotel owners had begun, by force of law or greed, to acknowledge that black money is green, too, Cosey’s resort starts emptying out. His daughter-in-law comes to hold the civil rights movement in disdain because it “destroyed her family and its business.”

Even as the black resort persisted through integration, it remained resistant to liberatory streams of black politics that were coursing through America. In the 1994 film The Inkwell, set in 1976, ex-Black Panther Kenny visits his sister at her Oak Bluffs summer home and bristles at the exclusivity of their surroundings. Spencer, his black Republican brother-in-law, teases Kenny about his politics. “Isn’t this what your struggle was all about? Huey and Bobby? An-gela?” Spencer asks, gesturing around during a trip to the beach. Kenny fumes. “And what about the black folks who weren’t allowed to make it? Where’s their Inkwell?” he asks. Spencer shrugs and offers: “Coney Island?” In his head, and in the heads of many others, the black community at the Inkwell is the result of a lot of hard work, the fulfillment of the American dream, the reward for making it. It doesn’t quite matter to Spencer that his own version of making it might not stand in for universal black success.

By the 1980s depicted in Sag Harbor, the Panther movement has waned, and the so-called post-soul generation is beginning to feel out its own ethnic path through the wake of the civil rights movement. One of Benji’s friends, adopting a revolutionary pose, “comes back to the Sag from his sophomore year of high school with a new, clipped pronunciation of the word whitey, and a fondness for using the phrases ‘white-identified’ and ‘false consciousness’ while watching The Cosby Show.” Eager to telegraph their resistance to a black elite they see as hewing too closely to white culture, Benji and his friends try on the slang, fashions, and music they associate with the “Street” — “Street being the antidote to Upper Middle Class emasculation,” Whitehead writes. The aesthetics and projected politics of the “Street” are antithetical to the ethos of the black resort.

Today, many black resorts are shadows of their former selves; the vacationers who remain do their best to preserve their pieces of history, but towns like Idlewild and Highland Beach now serve more as sites of memory than as active tourist destinations. In Idlewild especially, homes were abandoned after integration, and some of the businesses have become derelict, despite efforts at preservation. The “Black Eden,” as it was once known, had fallen.

Even strongholds like Oak Bluffs and SANS are under threat. In the 2023 novel Summer on Sag Harbor, Sunny Hostin’s second in a series of beach reads that take place in historic black resort towns, the decline of these spaces is the central conflict. The book is set in the summer after the George Floyd protests, when “Sag Harbor’s formerly tight-knit community of black elites was being threatened by developers who preyed on vulnerable, elderly homeowners” and families desperate for post-pandemic cash infusions. From 2009 to 2021, one character observes, SANS went from being 100 percent black to only 65 percent black. The novel’s protagonist, an investment banker named Olivia Jones, is “far from a revolutionary,” but she can recognize the pattern: “It was the same story in so many formerly predominantly black neighborhoods in the city — from Bedford-Stuyvesant to Harlem,” she observes. Fueled by the unsettled energies that might have driven other black elites into mutual aid work or the Diversity Equity Inclusion industrial complex, she gets involved in an organizing drive to keep the neighborhood out of the hands of whites. Nevermind that it’s an elite haven she’s struggling to protect.

For most of the novel, Olivia and her fellow organizers try to highlight the area’s historical and cultural significance. Joel Whittingham, the community’s “unofficial mayor,” recounts how Langston Hughes wrote poetry on his parents’ porch. “I think he wanted to refill his well, just like everyone else,” Mr. Whittingham says, in a succinct summary of the pitch for black resort towns. “But the unique thing about Sag Harbor is that he could truly rest among people who looked like him.” In the same scene, he also brags about his “dear friend, Colin Powell” (George W. Bush’s black secretary of state, who whitewashed the My Lai massacre, helped oversee the invasion of Grenada to topple its socialist government, and, most famously, lied to the United Nations to build support for America’s invasion of Iraq). Though Hostin seems relatively unconflicted about the ideal of the black resort — for her, these spaces represent an uncomplicated good, a genuine achievement — in her reference to Powell, she unintentionally clarifies the conservative undertow of the black resort as a political project. Near the novel’s close, Olivia decides she’s going to “create a company” that will fight development “through education, financial literacy programs, and cultural events.” Her goal, now, is to “avoid the destruction of historically black neighborhoods and cities.” Mr. Whittingham compares this effort to the civil rights movement. Are they sincere? Of course. But Olivia is also correct that there’s nothing “revolutionary” afoot — that Sag Harbor, or any other black resort, is not about change, but about a certain kind of privileged stasis.

In Great Expectations, David spots on his Vineyard host’s bookshelf a paperback copy of E. Franklin Frazier’s Black Bourgeoisie, a slim 1957 volume dedicated to unpacking the cultural politics of the black middle class. Frazier positions that group as isolated from the rest of the race’s struggles, its members modeling their aspirations on white paradigms of prestige and consumption. “Despite the tinsel, glitter, and gaiety of the world of make-believe in which middle-class Negroes take refuge, they are still beset by feelings of insecurity, frustration, and guilt,” Frazier writes. Cunningham doesn’t point out the irony of the book’s presence on Karen Cox’s shelf beyond noting that her copy is “frayed,” as if it has been a constant source of reference. Or perhaps a fetish for moments of reckoning? When Karen gives David a tour of the island, she exhibits a squirming pride about her status that Frazier would have had a field day analyzing. “We’re not like some of these people, you know, la-di-da,” she says. “At least we weren’t born that way. But look at us.”

Still perusing Karen’s bookshelf, David also finds her copy of The Wedding. Thumbing through, he notices that West dedicated the book to Jackie Onassis, who was her editor at Doubleday. David considers this a “little flash of fate,” because “the Senator reminded people of JFK.” The candidate’s political potential, David thinks, comes in part from his ability to assuage racial anxieties, his black-resort-brushed image that makes it feel good “to see Camelot in a guy who wasn’t white.” Pulling up to an event in Oak Bluffs, the candidate looks more relaxed than he has at any point in the book — “loose and untutored; his skinny frame swathed in a baggy white polo and a pair of sun-spotted chinos” — and more relaxed than we’ll ever see him again.

Of course, the real Obama not only fundraised at the Vineyard, as the fictional Senator does; he also continues to seek refuge there. In his 2020 memoir, A Promised Land, Obama briefly discusses his time on the Vineyard, where he was welcomed into the fold years before his national political debut by longtime summerer Valerie Jarrett. After that, he began renting a house in Oak Bluffs for short trips every other summer. “The place had a quiet beauty and unhurried vibe that suited us,” he writes. “We appreciated, as well, the Vineyard’s history.” Once president, Obama traded the ferry for Marine One and rented a bigger estate with room for Secret Service and staff. Summers on the Vineyard were a decidedly joyless experience for his daughters, part of the generation who will be responsible for keeping the flame of the black resort alive: “Arrangements were made for us to go to a private beach, empty for a mile in either direction,” Obama explains. “Our bike rides now followed a tightly prescribed loop, which the girls rode exactly once to indulge me before declaring it ‘kind of lame.’” Post-presidency, Obama bought a 29 acre, seven bedroom, $11.75 million Vineyard estate where he still cloisters himself for part of the year, away from politics.

As his ferry makes its way toward the Vineyard, David remembers a school lesson about how water in black literature always calls back to slavery and the Middle Passage. But he wonders if maybe the water is just water, “no bodies, no voices, nothing: just an illegible motion away from the city.” It’s hard to imagine that the members of the black resort class ever truly forget who they are or where their people come from, no matter how much physical and spiritual distance they put between themselves and the places where they’ve earned their leisure. Still, reaching a stratum as precarious as theirs requires a great deal of compromise, a compromise David strains to comprehend. He closes his sojourn on the Vineyard asking what Dorothy West must have thought about Mary Jo Kopechne’s drowning in Ted Kennedy’s car on Chappaquiddick, to what extent it had “troubled her idea of her hidden-away home.” Maybe there is a dark side to this dream, Cunningham suggests. This lifestyle might swallow you up before you can enjoy its fruits.