For more than a century, it was known to wealthy Blacks in New York and Boston as the “Black Hamptons” on Martha’s Vineyard, but a growing number of Chicago’s Black elite are flocking to the historic Black summer getaway
By Erick Johnson, Chicago Crusader
Meet Carrie Davis. She is the daughter of a surgeon and the mother of two highly successfully sons. For most of the year, Davis lives in Hyde Park—one block from former President Barack Obama—but during the summer, she packs her bags to live three months in a cottage on Martha’s Vineyard that costs more than six times the average mortgage.
As in years past, this summer, Davis will not be alone. While many Black Chicagoans prepare to hit Lake Michigan this weekend, hundreds of other affluent Blacks from Chicago will jet set to Oak Bluffs, Massachusetts, where they will live and play in ways many ordinary people of color will never be able to do in their lifetime.
The Kennedys boosted the profile of Martha’s Vineyard, but Black wealth and power have made Oak Bluffs an enduring summer playground that has outlived Michigan’s Idlewild and other historic seasonal Black destinations.
For more than a century, prominent and wealthy Blacks from New York and Boston have transformed this once segregated town in Martha’s Vineyard into what is known today as the “Black Hamptons.” Built by Black servants, Oak Bluffs is now a place to see and be seen, as America’s Black elite and well-heeled come to party hard in a town that’s delightfully stuck in time.
Victorian and gingerbread-style cottages have long been part of Oak Bluffs’ identity. Doctors, lawyers, prominent politicians and business magnates pull out the fedoras, beach sandals and sundresses for a season of fun and relaxation.
The biggest draw of the town is Inkwell, a historic narrow beach that has been a symbol of Black pride since the 1920s. The beach got its name from a number of Black writers who frequented the area for inspiration during the Harlem Renaissance.
Revered for its history and beloved for its laid-back atmosphere, Oak Bluffs’ popularity has remained steady over the decades, but in recent years, the appeal and popularity of “The Black Hamptons” has grown immensely with the help of a new and younger generation of Blacks who are inheriting homes that have been kept in the family for generations.
There is also a crowd of newcomers from across the country. Among them are prominent Blacks from Chicago. Some are retired. Others are moneyed executives who work hard and party hard. Many are drawn to Oak Bluffs’ laid-back atmosphere while others enjoy the non-stop hospitality of homeowners who never get tired of hosting social gatherings all summer long. An afternoon conversation can easily balloon into a party with lobster rolls, deviled eggs and blue cheese with crackers.
In addition to Davis, other Oak Bluffs jet setters from Chicago include McGhee Williams Osse, Co-CEO of Burrell Communications. Event promoters Steven and Dorothy Capers have put on a comedy show in Oak Bluffs for the last five years. Shirley Evans-Wofford, founder of one of the largest insurance firms in Chicago, Lambent Risk Management Services, makes the pilgrimage to Oak Bluffs during the summer.
Headquartered in Chicago, the Black college sorority, Alpha Kappa Alpha Sorority, Inc., has a massive annual beach party on Oak Bluffs’ Inkwell Beach with many of its members from Chicago.
“The whole beach looks like pink and green,” said Davis referencing the colors of the AKA sorority.
Seventeen years ago, Tracey Alston, who founded her successful public relations firm, the Danielle Ashley Group, was invited to come to Oak Bluffs by a cousin who had a friend who owned a cottage in the neighborhood. Before her visit in 2001, Alston had never heard of or been to Oak Bluffs, but was quickly won over by the town’s charm and vibe.
“It takes you back in time,” Alston said. “It’s one of those towns where there are screen doors that allow you to feel the breeze from the Atlantic in the house.”
Alston made several more trips to Oak Bluffs before she and six wo-
men and men held a tea party at one of the homes. What started out as a small gathering of about eight people has turned into a full-scale social affair that draws approximately 100 Black women every year. Many of the women are from Chicago.
Called “The Chicago Peaches,” the event is held the first Tuesday in August. Men relax and women wear hats, sip tea and munch on finger foods while catching up on the latest gossip. Alston said the atmosphere is not all prim and proper, but is one that is laid-back enough to allow them to be themselves.
“Last year, we were just enjoying ourselves and people kept coming,” Alston said. “Once you come, you become a peach and member of our group.”
Oak Bluffs’ regulars say Chicago residents steadily began coming to Oak Bluffs in 2005. Several Oak Bluffs fanatics told the Crusader that hundreds of Blacks from Chicago make Oak Bluffs their summer destination.
“It’s becoming more and more popular with Blacks in Chicago,” Davis said.
One famous Chicagoan, former White House senior advisor Valerie Jarrett, summers in Oak Bluffs. Dr. Martin Luther King, Jr. spent his summer there, along with Edward W. Brooke, the nation’s first Black senator elected since Reconstruction. Film director Spike Lee owns a house there. In 2009, the Obamas rented an estate in Chilmark, about 12 miles from Oak Bluffs.
In 1912, Charles Shearer, the son of a freed slave, founded a summer inn, Shearer Cottage, with his wife, Henrietta. The inn provided lodging for self-made millionaire Madam C.J. Walker, and singers Paul Robeson, Ethel Waters and Lillian Evanti. The Shearer Cottage is the oldest and most well-known of the establishments that catered specifically to Blacks.
Blacks on the island worked as servants for white homeowners, but with their earnings, they eventually became property owners, year-round residents and small business entrepreneurs, particularly in Oak Bluffs.
In the 1920s, these Blacks began to offer accommodations in their small cottages that attracted Black visitors from Boston, New York, Philadelphia, and other Northeastern cities. As Blacks grew more prosperous during and after World War II, many of them now brought their families to Oak Bluffs, whose people and culture have now spread across all of Martha’s Vineyard and includes far more people.
The history of Oak Bluffs is profiled in an extensive exhibit at the National Museum of African American History and Culture in Washington, D.C.
The most anticipated event at Oak Bluffs is the 16th Annual Run&Shoot Filmworks Martha’s Vineyard African American Film Festival. The event runs from August 6-11 and debuts the world’s top Black films before they hit the theaters.
During the year, there are about 3,713 permanent residents in Oak Bluffs according to the Martha’s Vineyard Commission. Though regarded as a Black enclave, only about three percent of Oak Bluffs residents are Black. During the summer season, Black tourists are among an estimated 10,637 seasonal vacationers in Oak Bluffs.
Hyde Park resident Davis has a summer home in the Bahamas. But she has spent the last seven summers in Oak Bluffs at the home of her son and his wife Jill, who spent her childhood on the resort. With her parents’ huge home and yacht, Jill introduced Davis and many of her friends to Martha‘s Vineyard. For 20 years, Christopher lived in New York and traded for a hedge fund on Wall Street. Her other son, Steve Davis, lives in San Francisco and has a private equity company. Two years ago, Christopher rented a house for $7,500 a week so she could enjoy some privacy while her son’s children and friends spent the summer in the other home.
In August, Alston and her friends will rent a 5-bedroom house in Oak Bluffs for two weeks during the film festival. It sits on the beach and rents for $10,000 per week, but the eight women will split the costs. With the endless string of parties and social atmosphere, Alston says it’s worth it.
Davis also has access to Blackpoint Beach, an exclusive private beach in Oak Bluffs where Davis said her son paid over $300,000 for a lifetime key to get in. She often sees the Obamas, who frequent Nancy’s, a popular seafood restaurant that’s less than a mile from Inkwell Beach.
Another Chicagoan, Carol Bell, Vice President of B. Coleman Aviation LLC, Executive Business Development for the powerful East Lake Management & Development Corp, first went to Oak Bluffs in 2013. In August, she will stay in Edgartown, an even ritzier neighborhood on Martha’s Vineyard that’s known for its fine, high-end restaurants. She plans to stay at the Harbor View Hotel, a beachfront hotel where she will pay for $450 per night for a room. Next door to the hotel, a famous Chicagoan, Executive Producer Shonda Rhimes, creator of ABC’s hit dramas Greys Anatomy and How to Get Away with Murder, rented a house for three years.
“I love the third week in August where the Blacks who owns homes put color lanterns outside their homes. It’s so beautiful. It’s like Christmas.”
Davis cannot wait to get back to her home away from home.
“This is the place to be,” Davis said. “It was always the Eastern thing, now it’s the Midwest thing.”