Celebs on Martha’s Vineyard

In honor of the 4th of July, here’s to the lowest-key celeb spot in the country: Martha’s Vineyard. This prestigious island is as Americana as it gets, so you can be sure that there’s no shortage of celebs on Martha’s Vineyard. It started with the Kennedys, who have had compounds here for decades. It’s now home to a huge number of famous summer residents. For tons of celebs, it’s a rite of summer to vacation on Martha’s Vineyard. These are the spots where they either try to blend into the crowd…or where they’re their usual conspicuous selves.

A Way of Life

Martha’s Vineyard isn’t just cool because it was the location of Jaws (the movie) in 1974. Or because the Obamas like to cozy up on a 28-acre plot of land on the island. Martha’s Vineyard is a full-on way of life for those who regularly make their summer trips here. Celebrities like Bill Murray, Meg Ryan, Reese Witherspoon, Mike Wallace, and even Princess Diana have all regularly visited. A number of them, such as Michael J Fox, have called the Vineyard their home. The low-key vibe is just one of the reasons the rich and famous make Martha’s Vineyard part of their summer circuit.

The Celebs: The Obamas

The Spot: Blue Heron Farm

You know that the Obamas know how to vacation, as their destinations frequently make our travel-goals list. So it’s no surprise that they are some of the regulars on Martha’s Vineyard in the summer. The former First Family stayed in the same $15 million property in Chilmark Pond — Blue Heron Farm — three years in a row. At the time, Obama was still in office, so his visit turned the low-key, press-free zone of Martha’s Vineyard on its head. Their entourage of security guards, friends, and fellow politicos (not to mention the paparazzi) caused road closures and all kinds of fanfare that lasted the whole summer.

Eventually, the family opted for beach and ice cream trips over handshaking and baby-kissing opportunities. But the private island remained one of the favorite and most consistent vacation spots for the Obamas. 

Blue Heron Farm features an exquisite infinity pool, as well as tennis and basketball courts. It’s set on 10 acres of rolling, grassy fields. Two guest houses made excellent places for the security detail to stay, at just the right distance from the family. The beach access and a boating dock on the private pond ensures the fun never stops. The house is also just a quick drive from a favorite seafood spot of theirs: Nancy’s in Oak Bluffs. Even the most powerful man in the world gets his hands greasy in a bucket of fried oysters.

Bill Clinton standing next to Obama at a podium.

The Celebs: The Clintons

The Spot: Mad Martha’s

Keeping with the presidential vibe, the Clintons are Martha’s Vineyard fixtures. It’s where they unwind, and where Hillary is known to have a beer or two. Their favorite ice cream spot, Mad Martha’s, is down to earth and unglamorous. The 50-year-old parlor that started in the back of a converted ambulance has a rustic, 1970s vibe. The handmade ice cream is as good as it gets. 

Mad Martha’s, which has outposts in Edgartown, Oak Bluffs and Vineyard Haven, has recently gotten new owners, who’ll be rejuvenating the iconic chain with a bevy of new flavors. We bet Bill Clinton is excited to try them all.

The Celeb: Bill Murray

The Spot: Oyster Bar 02557

No one expects Bill Murray to be super-highbrow when it comes to dining. He maintains his guy-next-door persona as a frequent visitor to the famed Oyster Bar 02557 in Oak Bluffs. Many celebs on Martha’s Vineyard love this place. Head chef Ben DeForest’s relatively new addition to the food scene on the island is only part of his local empire. DeForest’s original restaurant, Red Cat Kitchen, is a favorite of the Obamas. And the Obamas know their food and travel, so it’s a safe bet that anything DeForest does will be tasty.

On Martha’s Vineyard, it’s a ritual to relax with a cocktail or a glass of wine and some oysters to start out the evening. Oyster Bar 02557 is the place to be, with its famously good vibe and beautiful views. At the wraparound bar facing the water, guests can sip, dine, and watch the world go by. This spot is an ode to the classic clambakes that epitomize the location.

The Celeb: Spike Lee

The Spot: Mocha Mott’s

Spike Lee and his family enjoy spending part of the year on the island to escape the busy life in New York City. And by now he sure knows where to get a good cup of coffee. Mocha Mott’s is a popular stop-off for celebs on Martha’s Vineyard and it’s where Spike Lee enjoys grabbing his morning joe. The coffee emporium opened its doors in 1994, and takes pride in its organic and Fair Trade coffee, as well as in the homemade baked goods and Cape Cod bagels.

As one of Martha’s Vineyard’s notable (part-time) residents, Spike Lee definitely knows a thing or two about the island. You’ll be in good hands if you, too, stop at Mocha Mott’s.

Oprah standing next to Obama at a podium.

The Celeb: Oprah Winfrey

The Spot: Harbor View Hotel

We always trust Oprah on where to stay, eat, or vacation, and she does not let us down with her top pick for accommodations in the Vineyard. The seaside Harbor View Hotel in Edgartown has it all. Nowhere else has the perks of the beach and the feet-in-the-sand vibe, along with the proximity to local shopping and downtown dining.

The hotel has been a favorite of discerning travelers for over 130 years. and has seen its fair share of famous clientele. A recent $15 million renovation has upped the ante here, with new luxury amenities including a heated saltwater pool with VIP access to the Roxy Pool Bar, and Mercedeses to borrow. The suites have been redone to reflect the upscale and contemporary vibe. This isn’t The Hamptons, so no one rolls out the red carpet for anyone on Martha’s Vineyard, not even for Oprah. But at Harbor View, the staff do make every guest feel well taken care of.

The Celeb: Larry David

The Spot: State Road Restaurant

Comedy god Larry David is one of the many celebs who live on Martha’s Vineyard. We can only imagine what a swanky setup Larry has on his 70-acre plot of land. We hear it boasts an impressive outdoor stainless steel kitchen. When the kitchen isn’t being put to use, you can find him out in West Tisbury dining at the State Road Restaurant.

State Road Restaurant’s seasonally-focused menu items are all made from scratch, and the food is sourced from local farmers, food artisans, and fishermen. It’s a big hit with locals and tourists alike, so it’s no surprise that you can spot a semi-incognito celebrity here from time to time. If you’re looking to visit, the agricultural town of West Tisbury might be just the change you’re looking for. You may even come across the celebrated Seinfeld creator while you’re there.

The Martha’s Vineyard Icon: Jackie Kennedy Onassis

The Spot: Red Gate Farm

Here’s an homage to the political family that helped put Martha’s Vineyard on the map, and to the iconic former first lady. Even though most of the 340-acre property of Jackie O’s former Red Gate Farm is filled with wildlife, we don’t expect you’ll be able to get close to this historic mansion. But it’s worth mentioning because, well, it recently sold for $65 million. That price tag made it the most expensive property in Massachusetts.

The stunning grounds offers direct access to the coast, and they feature a vegetable garden, swimming pool, tennis and basketball courts, and a guest house. Jackie Kennedy designed the main house herself, with the help of architects Hugh Newell Jacobsen and Bunny Mellon. (Those two also worked with Jackie on the White House Rose Garden.)

The cozy cedar-shingled house is perfect for the family-oriented lifestyle Jackie Kennedy wanted. Except for the dining room, all of the rooms look out over the ocean. The house includes large windows, high-tech professional kitchen appliances and a warming fireplace to make the kitchen the heart(h) of the home. 

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