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Heading to Martha’s Vineyard? People speak of the iconic summer retreat as if it were one destination with one vibe. But dear reader, that’s just not so. There are five distinct social circles on Martha’s Vineyard, and they tend to gravitate toward specific places. Here’s our guide to what you need to know about social circles and socializing in Martha’s Vineyard ’cause once you understand that, the rest is easy.

what you need to know about socializing on martha’s vineyard

Every elite community has its own vocabulary. The sooner you learn to speak it, the more parties you’ll be invited to. For example, you must never, ever say that you are “in” MV. That’s a dead giveaway that you are a day-tripping arriviste. You are “on” Martha’s Vineyard.

To prepare you for these, and many other queries, as well as to ensure that you speak “Martha’s Vineyard” like a pro, we here at Dandelion Chandelier have prepared this handy guide to the social circles and socializing on Martha’s Vineyard.

We’ve collectively visited the island and carefully studied its mores and norms for more than 20 years (in some cases, many more), so consider this an informed overview. As with the Hamptons, there is not one Martha’s Vineyard – there are at least five. Distinct social circles that co-exist peaceably and even intermingle from time to time.

One of them is sure to be perfect for you.

The 5 social circles of MV. Photo Credit: Dandelion Chandelier.

the 5 social circles of martha’s vineyard

Here’s what you need to know about socializing on Martha’s Vineyard.

1. The Black Beau Monde.

Natural habitat:

Oak Bluffs; increasingly seen in Chilmark, Edgartown and Vineyard Haven. CEOs, financiers, writers, attorneys, surgeons, Ivy League professors and assorted other graduates of elite universities and their children can be found at play on MV from dawn through dusk. Members of the black upper class will find people from every stage of their lives here – childhood pals, college crushes, law school roommates, fraternity and sorority brothers and sisters, and business contacts of all kinds. Their roots here go deep: Martin Luther King Jr. vacationed in Oak Bluffs, as did Joe Louis, Harry Belafonte, and Dorothy West.

Favorite beach:

The Inkwell.

The Inkwell in Oak Bluffs.

Other socializing spots on Martha’s Vineyard to know:

Union Church on Sunday morning at 10:00A; Farm Neck Country Club with former President Obama; Linda Jean’s, Backdoor Donuts, the Sweet Life Café and Fat Ronnie’s in Oak Bluffs. If you love Sag Harbor, Harlem, Brooklyn Heights, Montclair, New Rochelle, View Park, or Hyde Park/Kenwood, welcome home.

If you visit:

Don’t forget your golf clubs, your Jack & Jill directory, your Obama 44 jersey and your casual—chic party clothes.

2. The In-Town Edgartown Aristocrats.

Edgartown covers a vast geography on Martha’s Vineyard – as a result, the elites can be found there in two distinctly different places. The first is the charming center of town, in the old whaling captains’ houses and a handful of newer homes that are right on the harbor. The homes – mostly either Greek Revival or Federal – are uniformly painted brilliant white with black shutters, nearly always have a pristine American flag flying prominently from the front porch, and are generally surrounded by picket fences and carefully-tended roses, morning glories, canna and hydrangeas.

Here, you’ll find captains of finance and industry, who are in some cases also captains of their own vessels. They’re quite possibly the last of the Rockefeller Republicans, so if you see them, treat them gently.

Favorite beach:

The one that their houses sit on. Second favorite is the secluded one near the Edgartown Lighthouse.

Other socializing spots on Martha’s Vineyard to know:

The Edgartown Yacht Club (the tennis courts or the harbor clubhouse); Atria, the Atlantic Club or The Port Hunter for dinner; the Lighthouse Grill at the Harborview for Sunday brunch. If you feel most at home in East Hampton Village, Greenwich, the Upper East Side, Bronxville, or Nantucket, you’ve found your people.

If you visit:

Be sure to bring your faded Nantucket reds, Sperry Top-Siders, paisley head-band, and a nice bottle of Macallan. If you’re feeling a bit sassy, you can sport a “Country before Party” button on your lapel. Other than that, any new or overtly political item of clothing will immediately mark you as an outsider – this is all about weathered, well-loved, deeply preppy attire worn with the utmost nonchalance. 

3. The Off-Road Edgartown Elite.

There are many members of the global elite who are quietly tucked away well off the beaten path, in deeply wooded areas that have waterfront access to the spectacularly lovely Edgartown Great Pond. They still have an Edgartown address, despite being miles away from the center of town. Like their counterparts on the harbor, here you will also find CEOs, financiers, professors and wealthy philanthropists – they’re just newer to the island and seeking far more privacy than in-town Edgartown permits.

Favorite beach:

Their kids love South Beach; the older generation loves the private sandy shoals available only to them and their neighbors.

Other socializing spots on Martha’s Vineyard to know:

The bike paths around Katama; Morning Glory Farm; 19 Raw Oyster Bar for cocktails; Beach Road and State Road for dinner. If you love Amagansett, Aspen, Scarsdale or Beverly Hills, now you know where to go.

If you visit:

Bring your Leica (the scenery is jaw-dropping), several pairs of sturdy shoes (many of the roads remain unpaved) and a detailed map of the island – GPS’s don’t tend to work here, and these exquisite homes can be devilishly hard to find, especially at night.

Morning Glory Farm. Photo Credit: Dandelion Chandelier.

4. The Artisanal Up-Island Avant-Garde.

You could also call this social circle the Chilmark Chill Crowd or the Artists of Aquinnah. They’re educators, writers, artists, politicians, people who work in creative fields, makers and those who want to enjoy some time off the grid (the cell service is terrible in this part of the island). It’s been this way for generations. Jacqueline Kennedy Onassis and her family maintained one of the largest estates on the Vineyard up-island in Aquinnah for more than 30 years. And comedian John Belushi is buried here.

Socializing on Martha’s Vineyard with this crowd means staying close to the earth. People who choose this part of the island today tend to seek out artisanal products and local food. You’re likely to find those who love to cook, host friends for dinner, and spontaneously catch the sunset. There are sheep farms, stables, art galleries and nature preserves nearby.

Favorite beach:

Lucy Vincent; second favorite is Aquinnah Cliffs beach.

Other socializing spots on Martha’s Vineyard that to know:

The Menemsha docks at sunset; The Yard for dance performances; Alley’s General Store; the Home Port or Menemsha Fish Market for dinner out. If you love Montauk, Greenwich Village, Berkeley, or Austin, walk this way.

If you visit:

Don’t forget to bring your #Resist T-shirt, your flip-flops, some craft beer and a biting sense of humor.

social circles and socializing on martha's vineyard

5. The West Chop Club Kids.

Tucked away in a section of Tisbury, on the north end of the island, is a neighborhood known as “West Chop.” It’s so named, alongside its counterpart “East Chop” in Oak Bluffs, because it sits on a peninsula surrounded on one side by the Vineyard Sound and on the other by Vineyard Haven Harbor.

Here, you’ll find a historic lighthouse, spectacular gray cedar-shingled mansions with killer views of the sound and its boats, sunset views that rival those of any on the island, and a small community of wealthy people who are little known to those who aren’t regular visitors to the island.

That’s in part because there are only two roads into and out of the community, making it feel more exclusive and private. It’s also in part because the residents like it that way, and don’t want any outside attention. For generations, the vibe here has been about being a member of the club, sometimes literally. Traditional community activities in West Chop include sailboat races, art shows, costume balls, baseball games, tennis tournaments, and communal picnics that have been held every summer since the early 20th century.

Favorite beach:

The private one on which their homes sit, natch.

Other socializing spots on Martha’s Vineyard to know:

The members-only West Chop Club for meals and tennis; and Garde East for dinner. If you like Tuxedo Park, Jackson Hole, Kiawah Island or The Greenbrier, you’ll fit right in.

social circles and socializing on martha's vineyard

West Chop on Martha’s Vineyard at sunset.

If you visit:

Bring your tennis whites and a pair of binoculars so you can see the lively tableau playing out on the Sound.

a final word about social circles on Martha’s Vineyard

A few final things you need to know about socializing on Martha’s Vineyard.

Note the absence of any discussion of fancy cars. Unlike the Hamptons, the Vineyard is not at all about what you’re driving. Traditional status markers don’t exist here: extremely wealthy and powerful people tool around in decades-old mud-covered Jeeps.

The happiest news of all? You can’t really dress up on MV, even if you want to.  When socializing in Martha’s Vineyard, there’s no place where a jacket and tie are truly necessary. And high heels just don’t work on the narrow cobblestone sidewalks and sandy beach paths (and certainly not on a boat).

Finally, no matter which social circles you choose to hang with on Martha’s Vineyard, the social norm here is New England laconic. Whether it’s where you went to university, what you’re driving, or who you’re wearing, no one is interested in talking about it. The one true social taboo? Being a show-off, a name-dropper or a loud-mouth. The occasional humble brag is OK.

social circles and socializing on martha's vineyard

East Chop, Oak Bluffs, Martha’s Vineyard.

You see why we view Martha’s Vineyard as a paradise?

Just come as you are. And make the island your own.

Pamela Thomas-Graham

Pamela Thomas-Graham is the Founder & CEO of Dandelion Chandelier. She serves on the boards of several tech companies, and was previously a senior executive in finance, media and fashion, and a partner at McKinsey & Co.