Honestly, if you ask three different people what Martha’s Vineyard is famous for, you’re going to get three completely different answers. One person might immediately bring up the Obamas or the Clintons. Another will start gushing about the clay cliffs in Aquinnah. A third—probably someone who grew up in the 70s—will tell you it’s where a mechanical shark named Bruce terrorized a bunch of actors in Jaws.
They’re all right.
The Vineyard is a weird, beautiful contradiction. It is 100 square miles of land sitting about seven miles off the Massachusetts coast, and yet it feels like its own sovereign nation. It’s a place where you can find a $39 million estate in Chilmark just down the road from a working fishing shack in Menemsha where the floorboards are sticky with salt.
The No-Chains Rule and the "Down-Island" Vibe
One of the first things you notice when you roll off the ferry in Vineyard Haven or Oak Bluffs is what’s not there. No Starbucks. No McDonald’s. No Marriott. The island is famous for its fierce, almost obsessive protection of local business. Because of this, the six towns on the island have managed to keep a vibe that feels increasingly rare in 2026.
People usually split the island into "Down-Island" and "Up-Island."
Down-Island is where the energy is. You’ve got Oak Bluffs, which is famous for the Gingerbread Cottages. These aren't just cute houses; they are a collection of over 300 brightly colored, Carpenter Gothic-style cottages in the Methodist Camp Meeting Grounds. They look like someone tried to build a town out of dollhouses. Right nearby is the Flying Horses Carousel, which is actually the oldest platform carousel in the United States, built in 1876. You can still grab for the brass ring there.
Then there’s Edgartown. This is the "white picket fence" part of the island. It was an old whaling port, and the wealth from that era is still visible in the massive, stately captain’s houses lining the streets. It’s polished. It’s where you go for high-end gallery hopping and to see the Harbor View Hotel, a landmark that’s been hosting celebrities and world leaders since the late 1800s.
Why the Vineyard Is "Hollywood East"
You can't talk about what Martha's Vineyard is famous for without mentioning the star power. But here’s the thing: the island is famous for ignoring the celebrities.
Sure, it’s a massive summer destination for the elite. The Obamas famously bought a nearly 30-acre estate on the Edgartown Great Pond. Bill Clinton was a regular. Larry David is a resident. Carly Simon has lived there for decades. But the "Vineyard Way" is basically to let these people buy their groceries and bike to the beach without making a scene.
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- The Inkwell: For over a century, Oak Bluffs has been a premier vacation spot for African American families. Famous residents and visitors like Maya Angelou, Spike Lee, and Reverend Adam Clayton Powell Jr. helped cement the island's reputation as a place of Black joy and excellence.
- The Kennedy Connection: The family is synonymous with the region. While they are often associated with Hyannis Port on the Cape, the Vineyard has been the site of their greatest triumphs and most public tragedies, including the Chappaquiddick incident in 1969 and the 1999 plane crash of JFK Jr.
The Mystery of the Name (and the Missing Grapes)
Here is a bit of trivia that usually wins people over: There are no commercial vineyards on Martha's Vineyard.
It’s kind of a scam, right?
The name comes from 1602. A British explorer named Bartholomew Gosnold landed there and found a ton of wild grapes. He had a daughter named Martha (or maybe a mother-in-law, historians argue about this), and he just slapped the name on the map. It stuck. Before the English arrived, the Wampanoag people called the island Noepe, which translates to "land amid the streams."
The Quiet Side: Up-Island and the Aquinnah Cliffs
If you drive west, the trees get shorter, the stone walls get more frequent, and the crowds disappear. This is Up-Island—West Tisbury, Chilmark, and Aquinnah.
Aquinnah is world-famous for its clay cliffs. They are stunning. Red, orange, and white clay towers over the Atlantic. This area is also the ancestral home of the Wampanoag Tribe of Gay Head. It feels ancient. It’s quiet.
Down the road is Menemsha, a tiny fishing village in Chilmark. If you want to experience the true soul of the island, you go to the fish market there, buy a lobster roll, and sit on the beach to watch the sunset. It’s a ritual. Even in 2026, with all the changes in the world, that sunset at Menemsha remains one of the most photographed things in New England.
A History You Probably Didn't Know
One of the most fascinating things about the Vineyard’s history is its "hereditary deafness." For nearly 200 years, a significant portion of the population on the island—specifically in Chilmark—was born deaf due to a recessive gene.
Because so many people were deaf, the entire community developed its own sign language called Martha’s Vineyard Sign Language (MVSL).
What’s wild is that everyone used it. Hearing people, deaf people—it didn't matter. It was a completely bilingual community where being deaf wasn't seen as a disability because there were no communication barriers. The last person to use MVSL passed away in the 1950s, but that legacy of inclusion is a huge part of the island’s historical DNA.
The Movie That Changed Everything
In 1974, a young Steven Spielberg showed up with a mechanical shark. He filmed Jaws almost entirely on the island.
The locals were used as extras. The "Jaws Bridge" (officially the American Legion Memorial Bridge) between Edgartown and Oak Bluffs is now a tourist landmark. Every summer, hundreds of people jump off that bridge into the water below, despite the "No Jumping" signs.
The movie put the island on the global map in a way that whaling and Methodist camp meetings never could. It turned the Vineyard into a "bucket list" destination.
Actionable Next Steps for Your Visit
If you're planning a trip to see what makes this place so legendary, keep these things in mind:
- Book the Ferry Early: If you’re bringing a car, you need to book your Steamship Authority reservation months in advance. In 2025, they did $7 million in sales on the first day of bookings.
- Rent a Bike: The island has over 44 miles of bike paths. It’s the best way to see the gingerbread cottages and the state forest without dealing with the island's "no traffic light" congestion.
- Visit the Museum: The Martha's Vineyard Museum in Vineyard Haven is actually worth your time. It’s in an old marine hospital and explains the Wampanoag history and the whaling era better than any tour guide.
- Eat Local: Look for the "Morning Glory Farm" label or hit the West Tisbury Farmer’s Market. The island is obsessed with its agriculture, and the food quality reflects that.