The Ultimate Black Culture Guide to the Best of Martha’s Vineyard

Editor’s note: First published in June 2019. Martha’s Vineyard is well-known as the summer home of the black elite. But really, it’s the summer of home of black heritage, black excellence, and black friends and family. If you’re planning to visit Martha’s Vineyard this summer, what are the best places to see, stay, and dine on the island? Especially if you’re seeking the iconic black experience on Martha’s Vineyard that African-American families have had since the late 1890’s? We went straight to the expert. Author of Our Kind of People, Lawrence Otis Graham, shares the ultimate Black and African-American culture guide to the best of Martha’s Vineyard for families, first-time visitors and more.

The Ultimate Black Culture Guide to the Best of Martha’s Vineyard

Editor’s note: First published in June 2019.

During the summer months, the population of this 100-square-mile island can reach over 100,000 people -many of whom are members of the black community. African-American families visiting Martha’s Vineyard will find a beautiful, welcoming, and diverse community filled with black culture. Here’s what you need to know if you want to experience the island the way black families have for generations.

1. How do people get to Martha’s Vineyard?

You Can Fly In

When people are pressed for time, or coming out for the weekend after working all week, like my father used to do when we were kids, they fly into the Martha’s Vineyard airport (MVY).  JetBlue and Cape Air fly direct from Boston and New York. American also has some flights into the island. If you fly in, be sure to book a rental car, because while there’s bus and taxi service on the island, that can be a slow and somewhat unpredictable way to get around.

You can take the ferry

As glamorous as it may sound, though, flying to the island is not nearly as authentic and socially entertaining as taking the ferry. There are a number of “fast ferries” and private commercial ferries available from New Bedford and Cape Cod.

But most folks take the Massachusetts Steamship Authority ferry. It’s the iconic way to travel to Martha’s Vineyard, and it doesn’t matter much whether you take one to Oak Bluffs or to Vineyard Haven.

The party starts in the parking lot at Wood’s Hole when people line up in their cars for the trip. You’ll see people you haven’t seen since last summer getting the papers or a snack, walking their dog, or just hanging out.  Once on board, it’s a great chance to catch up, people-watch, and starting getting your head into the Vineyard vibe.

However you travel, don’t over-dress.

The key to fitting in upon arrival is not dressing up too much. There’s no need for jacket and tie or high heels – you can spot first-time visitors because they think it’s like the Hamptons, where you have to spend an hour getting ready before you show up anywhere. The Vineyard look is vaguely preppy, a little bit nautical, extremely relaxed and assured, with a subtle nod to your tribe. Like a sweatshirt that says Howard or Spellman or Exeter or Harvard. Or “Sag Harbor.”

yes, you need a car.

You’re going to want a car on the island, and the ferry means you can bring your own. If you can’t get a ferry slot, though, you can rent a car on the other side.

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2. What are the top “must see” sites, or experiences, or activities on Martha’s Vineyard, especially for black families?

Oak Bluffs

Start in Oak Bluffs. That’s traditionally been the center of the black experience on the island. Walk down Circuit Avenue, where you can find lots of shops and places to eat.

Take a ride on the historic Flying Horses. Stop by Nancy’s, where the daughter of former President and First Lady Barack and Michelle Obama worked a summer job a couple of years ago.

Visit the Methodist Campground, where charming gingerbread houses circle a wide green space.

Walk, bike or drive over to East Chop, which has incredible views of the Bay. The lighthouse there is a good destination. From there you can see iconic scenery of a Martha’s Vineyard summer.

On Sunday, everyone – and I do mean everyone – attends the service at the Union Chapel in Oak Bluffs. The guest ministers change each week and they are phenomenal. Reverend Calvin Butts of Abyssinian Baptist Church has preached there for the past two summers. In the pews you’ll find candidates running for office. And elected officials like Ayanna Pressley, Massachusetts’ first black Congresswoman.

Word to the wise: if you want a seat, you need to be there 45-60 minutes before the service starts. It’s standing-room only by the time the service starts, and some people stick their heads through the church windows to hear the sermon.

And then go to Ocean Park. You can hang out on a blanket, fly a kite, and be in the center of everything. That’s the best place to view the fireworks on the second Friday in August.

Or rent bikes and ride from Oak Bluffs to Edgartown. The bike path is paved and well-marked, it’s reasonably flat, and you’ll pass great scenery. There are stops along the way for ices and cold beverages. And you never know who you might see on the bike path.

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Vineyard Haven

The Bunch of Grapes Bookstore on Main Street is a still an important stop on any visit to the island, even though it has moved from its original location and is smaller now than it used to be.

The Black Dog Tavern is something to do at least once, since it’s become something of a legend for those off the island. Definitely do breakfast, and arrive early if you don’t want to wait (the lines can grow to an hour or more in busy times of day).

The Martha’s Vineyard Agricultural Fair is not-to-be-missed if you’re on the island in mid-August. It’s always on the second week of the month in West Tisbury. This is the quintessential country fair: animals, livestock shows, tractor pulls, carnival rides. And llamas. The fresh-squeezed lemonade alone is worth the price of the ticket.

Edgartown

There was once a time when black people didn’t feel welcome walking around the narrow streets of Edgartown. Thankfully, that era is over, and you’ll see black people there just the way you would in Vineyard Haven and other parts of the island. Edgartown is now officially part of the black experience on Martha’s Vineyard.

There are great shops and restaurants there, as well as the famous white clapboard Captain’s Houses, with their widow’s walks facing the sea. You’ll find flowers and American flags everywhere you go – and there are lots of benches for people-watching.

Aquinnah

The red-clay cliffs at Gay Head are definitely worth the trip, even though they’re about 30 minutes away from where most people are staying. Property of the Wampanoag Tribe, you’ll find incredible views, snacks, and souvenirs.

The Heritage Trail

The Martha’s Vineyard Black Heritage Trail is a great way for African-American families visiting Martha’s Vineyard to fully experience the richness of black history on the island. You might be surprised to learn the diverse and wide-spread impact of African-Americans on the island. Its not all about Oak Bluffs. For example, Frederick Douglass made an important speech at the Old Whaling Church in Edgartown.

3. Favorite beach?

Hands down, the Inkwell. That’s always been the beach where African-American families have gathered. You’ll see folks there from sunrise to sunset – teenagers, families with young kids, groups of friends. It’s a wonderful experience. It’s on the Bay side of the island, so the water is really calm. The sand is rocky, but no one cares.

Some African-American teens and young adults will go to South Beach, which is on the ocean side of the Vineyard, because the waves are big. Its where the cool kids like to hang out, and its a pretty easy bike ride from Oak Bluffs and Edgartown.

4. Favorite restaurant?

Lots of African-American families on Martha’s Vineyard head to Linda Jean’s on Circuit Avenue in Oak Bluffs for breakfast. And at Lola’s, on Beach Road between Oak Bluffs and Edgartown, for dinner. Everyone loves Back Door Donuts in Oak Bluffs. And Giordano’s pizza is outstanding.

The Net Result in Vineyard Haven has the best fried seafood on the island, if you ask me. A lot of folks swear by Grace Church Lobster Rolls in Vineyard Haven. Every Friday night in the summer they serve lobster rolls, hot dogs, clam chowder, and pie. The proceeds go to benefit the church.

We also like Behind the Bookstore in Edgartown for breakfast or lunch.

For snacks and treats, you can’t beat Mad Martha’s ice cream and Murdick’s fudge. My family waits all year for a taste of Murdick’s fudge.

Morning Glory Farm in Edgartown is the go-to for fresh produce. It also has some of the best baked goods, including pies, anywhere on the island.

And in Menemsha, the Home Port is one of our favorites – it’s a classic seafood “shack” with a great menu and staff, and you can catch the sunset after dinner at Dutcher Dock.

5. What are the big annual events, traditions, or other elements of community life that black families would want to know about?

July Fourth

The Fourth of July is a big deal on Martha’s Vineyard. There’s an annual early-morning swim at the Inkwell where a group of black residents and visitors called “the Polar Bears” join hands in a circle in the water to welcome the official opening of the summer season. There’s an annual parade in Edgartown, too.

Illumination Night

If you’re on the island in mid-August, the Grand Illumination (aka Illumination Night) is held here every year on the second Wednesday of August. It’s been a tradition since the 19th century, and it’s a special experience. The owners of the cottages decorate with Japanese lanterns and after dark they turn them all on at the same time. There’s a community sing beforehand.

Martha’s Vineyard African American Film Festival

The first week in August sees the annual Martha’s Vineyard African American Film Festival; screenings are held at the Performing Arts Center in Oak Bluffs.

The Oak Bluffs Fireworks

People also turn out for the fireworks on the second Friday in August. The best place to see them is from the Oak Bluffs waterfront, either in Ocean Park or close-by.

But a lot of the joy of the life of African-American families on Martha’s Vineyard in summer is not having to make big plans. You will see someone you know almost anywhere you go, and you can make a spontaneous dinner date or bike ride plan without a lot of forethought. There are lots of house parties and impromptu gatherings that happen organically.

This summer, there will be lots of political fundraisers, so people will definitely be turning out for those.

6. If you’re renting a home, what part of the island is core to the experience of black families on Martha’s Vineyard?

Oak Bluffs is the beating heart of the black experience on Martha’s Vineyard, so if you want to be right in the middle of everything, that’s where you should rent.

More and more, though, people have started spreading out – renting in Vineyard Haven, Sengekontacket Pond, even Edgartown. If you want real seclusion, you can consider “Up Island.” When the Obamas are on island, they stay in Chilmark, where they can be far away from prying eyes.

You can divide Martha’s Vineyard into “up-island” (the west) and “down-island” (the east). If you’re one of the many African-American families vacationing on Martha’s Vineyard and looking for lots of social activity, you want to be down-island.

7. What are 2-3 places you’d suggest as good inns or hotels to stay?

The Summercamp Hotel (formerly The Wesley Hotel) is right in the middle of everything in Oak Bluffs. It changed ownership a couple of summers ago, and it gets good reviews.

In Vineyard Haven, we have friends who swear by the Mansion House.

In Edgartown, the Kelley House is perfectly situated right by the harbor. The Richard is a newly-renovated 16-room boutique hotel on Main Street in Edgartown.

8. What’s new — or relatively new — on the island this summer that people should be sure to check out?

Here are just a few updates of particular interest to African-American families heading to Martha’s Vineyard this summer.

• The new location of the Martha’s Vineyard Museum is open in Vineyard Haven.
• Two plaques honoring Confederate soldiers have been removed and covered with plywood after a unanimous vote of town selectmen.
• Lola’s is a beloved element of the iconic black experience on Martha’s Vineyard. So folks will want to know that owner Kathy Domitrovich has sold to a new owner – the restaurant will be managed by Doug Abdelnour Jr., the owner of Nancy’s Snack Bar in Oak Bluffs.
• The Harbor View Hotel in Edgartown closed for renovations over the winter. It’s now open again with two new restaurants: Roxana Bar and Bettini helmed by chef Patrice Martineau, a veteran of Daniel Boulud’s New York restaurant empire. There’s also a new Presidential Sky House in a formerly unused space, featuring a four-bedroom, five-bathroom suite and spectacular views.

Did I miss anything? Have a great time on the Vineyard this summer. See you at the Inkwell.

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Editor’s update: The author, Lawrence Otis Graham, passed away on February 19, 2021. Married for almost 30 years to the Founder of Dandelion Chandelier, Pamela Thomas-Graham, beloved father of their three children, this post remains on our site in memory of his joy, pride and love for Martha’s Vineyard and its rich Black heritage. And in honor of the glorious family days we were lucky enough to share there as a family.

Lawrence Otis Graham is a real estate attorney in New York and is a New York Times bestselling author of 14 nonfiction books including Our Kind of People: the History of America’s Black Upper Class (HarperCollins). 20th Century Fox is developing the book into a television series. A graduate of Princeton University and Harvard Law School, his work has appeared in The Best American Essays, Reader’s Digest, The New York Times, and U.S. News & World Report, where he has served as a contributing editor. Graham has appeared on The Today Show, ABC News’ Nightline and other programs. He sits on the boards of the Horace Mann School, Eaglebrook School, and University of Pennsylvania.