Martha’s Vineyard has long captured the attention of celebrities, politicians, and vacationers alike. Its charming villages, serene beaches, and historic lighthouses make it a highly sought-after retreat. Beyond its picturesque landscapes, the island carries deep historical significance, having hosted American icons, from the Kennedy family to Carly Simon, and more recently, the Obamas.
Yet, the island’s history also includes tragic events that have left a lasting imprint on the Kennedy family and the nation.
Located off the coast of Massachusetts in the Atlantic Ocean, Martha’s Vineyard sits near Nantucket and Cape Cod, both popular summer destinations. European settlers arrived in the early 1600s. The island’s name is believed to honor either the mother-in-law or daughter of English explorer Bartholomew Gosnold, who explored the area in 1602.
The 19th century brought prominence to Martha’s Vineyard through the whaling industry. Wealthy sea captains and Boston merchants purchased land and established estates, setting the stage for the island’s transformation into a summer haven for the affluent.
Today, the island has a year-round population of approximately 20,530, which swells to around 200,000 during the summer months.
The Kennedy Compound
In 1928, Joseph Patrick Kennedy, patriarch of the Kennedy family, purchased a small holiday cottage on the island. By 1941, 50 Marchant Avenue in Hyannis Port became the family’s full-time home, where Joseph and Rose Kennedy raised their nine children. Neighboring homes were later acquired by their sons, creating the famous Kennedy compound.
John F. Kennedy announced his 1960 presidential campaign from Martha’s Vineyard. After his inauguration in January 1961, he used the island as a presidential retreat, often referred to as the “Summer White House,” until his assassination in 1963.
The Chappaquiddick Incident
Martha’s Vineyard was the site of another high-profile Kennedy event on July 18, 1969.
Edward “Ted” Kennedy drove Mary Jo Kopechne from a party on Chappaquiddick Island when his car plunged into a pond. Kennedy escaped while Kopechne tragically drowned. He later pleaded guilty to leaving the scene of an accident and received a two-month suspended sentence.
The incident affected his presidential ambitions but did not end his long Senate career.
Celebrity Residents and Visitors
By the late 1960s, Martha’s Vineyard attracted numerous celebrities. Frank Sinatra and Mia Farrow were among the early visitors, and Farrow purchased a home on the island in the 1970s after her divorce.
Singer Carly Simon moved to Martha’s Vineyard in 1971 with musician James Taylor. The couple transformed a modest shack into a sprawling mansion known as Hidden Star Hill. After their divorce in 1983, Simon remained on the island, raising her two children and showcasing the island to the world through her televised concert “Carly Simon: Live from Martha’s Vineyard” in 1987.
Other celebrity homeowners and regular visitors include Spike Lee, Ted Danson and Mary Steenburgen, Larry David, Bill Murray, and politicians such as Bill and Hillary Clinton. The island also hosts the Martha’s Vineyard African American Film Festival, adding to its cultural significance.
Jackie Onassis and Red Gate Farm
Jacqueline Kennedy Onassis, John F. Kennedy’s widow, became one of Martha’s Vineyard’s most notable residents. In 1979, she purchased 137 hectares at Red Gate Farm, developing a Cape Cod-style house where she hosted celebrities and politicians, including Bill Clinton.
Caroline Kennedy described the property as a place her mother cherished after raising her children. Parts of Red Gate Farm were later sold, while Caroline retained 38 hectares, including the main house.
The Obamas’ Estate
In 2019, former President Barack Obama and First Lady Michelle Obama purchased an 11-hectare estate in Edgartown. The property gained widespread attention when Barack celebrated his 60th birthday there in 2021.
The star-studded guest list originally included 500 attendees, though it was scaled down due to a COVID-19 surge. Notable attendees included John Legend and Chrissy Teigen, Tom Hanks and Rita Wilson, Steven Spielberg, Bradley Cooper, and Gayle King.
Tragedies Linked to Martha’s Vineyard
The island has also witnessed profound tragedies for the Kennedy family. In 1999, John F. Kennedy Jr., his wife Carolyn Bessette-Kennedy, and her sister Lauren died in a plane crash en route to Martha’s Vineyard.
Kennedy Jr., who held a pilot’s license for only 15 months, was not qualified to fly the plane at night using instruments. The crash occurred on July 16, 1999, just 12 kilometers from the island, with all three bodies later recovered and their ashes scattered nearby.
Most recently, Martha’s Vineyard was connected to the death of Caroline Kennedy’s daughter, Tatiana Schlossberg. She passed away from a rare mutation of acute myeloid leukemia in 2024. A family photo released shortly before her funeral showed Schlossberg with her husband, George Moran, and their children at the island, where she had celebrated her wedding eight years earlier.
The island continues to blend natural beauty, historical significance, and celebrity allure. Its six towns retain charm while welcoming thousands of visitors each summer. From the Kennedy legacy to modern political figures and renowned artists, Martha’s Vineyard remains a symbol of both leisure and historical resonance on the American East Coast.
