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The African-American Heritage Trail on Martha’s Vineyard

Discover more about the Island’s history with a walking tour of the African American Heritage Trail.

The African American Heritage Trail of Martha’s Vineyard is a compilation of 30 different sites dedicated to previously unrecognized contributions made by people of African heritage, to the island of Martha’s Vineyard. Every site has a commemorative plaque describing each contribution. 

The organizers, the African American Heritage Trail History Project , are a non-profit corporation, invested and dedicated to the research and sharing of the history of the African American people on the island of Martha’s Vineyard. Most importantly, the work is to identify these sites and place a bronze plaque to honor that person and contributions. 

This project is a way to get the community involved in the education and celebration of the research that is discovered and showcased. 

“For several years, the history classes at the Martha’s Vineyard Regional High School were involved as research assistants in the work of the Trail and acted as tour guides, site maintenance staff, mural painters, website developers, and musicians. Several graduates of that program now work with us during the summer season to share their knowledge with our visitors.  We continue to work in the Island schools.”

The Mission of the Trail is to continue to research and publish previously undocumented history and to involve the Island community in the identification and celebration of the contributions made by people of color to the island of Martha’s Vineyard. 

While you’re on the island, you can book a few different trails to explore via a walking tour with expert tour guides:

• Oak Bluffs ($40)
• Oak Bluffs and Edgartown ($60)
• All Island Tour ($80) - this tour is not walking and has a stop at the Aquinnah Cliffs as well 

You can book a tour on their website, MV African-American Heritage Trail tours . They also have books available to support their organization, such as Lighting the Trail: African American Heritage Trail of Martha’s Vineyard , written by the founders of the trail, Elaine Cawley Weintraub and Carrie Camillo Tankard.

If you’re looking to discover and learn more about the Island’s history, a walking tour that will teach you the most important contributions to the island by African American community members, is the way to go. 

You can read more articles about the African American Heritage Trail in the Vineyard Gazette . Be sure to follow them on Facebook and Instagram for the most updated information.

Explore Martha's Vineyard Towns

African-American Heritage Trail

  Places To Go & Things To Do  

African-American people have been part of Martha's Vineyard history since before the American Revolution.

Their experience has embraced all aspects of Island Life. As early as 1703, estates included enslaved persons and there is evidence of an African-American history from that time until the present day. Records show their work as seamen, preachers, wise women and even sea captains. Remnants of buildings include churches, homes and social clubs. Methodism is believed to have been brought to the Island by John Saunders and his wife. They were formerly enslaved people who purchased their freedom in Virginia and traveled to Holmes Hole. They arrived on the Island in 1787 and John being an exhorter preached occasionally to the people of color at Farm Neck" There is a rock in the Farm Neck area known as Pulpit Rock where the preacher stood to exhort and spread the word of God

The African American Heritage Trail | P.O. Box 234, West Tisbury, Mass. 02575 | Tel: 508-693-4361

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Welcome to the Martha's Vineyard African-American Heritage Trail. There are currently 39 sites on the Heritage Trail. Close this box to view the sites on the map.

For more information please visit our website at: MV African-American Heritage Trail

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May 19, 2020

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.

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.

Martha’s Vineyard Steamship Authority Ferry. Photo Courtesy: The Martha’s Vineyard Times.

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.

More on Martha’s Vineyard

The best of what’s new on martha’s vineyard this year, 2. what are the top “must see” sites, or experiences, or activities on martha’s vineyard, especially for black families.

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.

The Flying Horses Carousel in Oak Bluffs, Martha’s Vineyard

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

Gingerbread Houses in Oak Bluffs, Martha’s Vineyard

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.

Union Chapel in Oak Bluffs, Martha’s Vineyard

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 .

The Ocean Park Gazebo on Martha’s Vineyard. Courtesy Photo.

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.

Former President Obama and daughter Malia biking on Martha’s Vineyard

why is Martha’s Vineyard so important to the black elite?

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.

The annual Martha’s Vineyard Agricultural Fair in West Tisbury, MA

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.

Edgartown, 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.

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.

Gay Head Cliffs in Aquinnah, Martha’s Vineyard

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.

Author Lawrence Otis Graham shares a black experience culture guide to the best of Martha’s Vineyard for African-American and all families.

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.

The Polar Bears on July 4th at the Inkwell Beach on Martha’s Vineyard. Photo Courtesy: The Vineyard Gazette.

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.

Lawrence Otis Graham shares tips on how to experience Black culture on Martha’s Vineyard. The Grand Illumination in Oak Bluffs. Photo Credit: Mark Lovewell, Vineyard Gazette.

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 African-American Film Festival on Martha’s Vineyard. Photo Courtesy The Vineyard Gazette.

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.

Author Lawrence Otis Graham shares a black experience culture guide to the best of Martha’s Vineyard for African-American and all families. The annual August fireworks in Ocean Park Oak Bluffs.

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.

Lawrence Otis Graham shares tips on how to experience Black culture on the island: Homes in the East Chop section of Oak Bluffs, Martha’s Vineyard.

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.

Lawrence Otis Graham

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A Black-owned guide to Martha’s Vineyard

Where to eat, stay, and play in a legendary beach getaway of black america..

Martha’s Vineyard, MA , shares a rich history with the African American community. For more than 100 years, the Vineyard has provided a place for Black Americans to gather and unwind and for many entrepreneurs to start businesses.

Originally a whaling community, Martha’s Vineyard is divided into six towns; among them, Oak Bluffs , which was immortalized in the 1994 movie The Inkwell , about an inner-city kid’s trip to visit wealthy relatives on the Vineyard. The Bluffs started garnering attention again after the Obamas visited multiple times as America’s First Family. John Legend and Chrissy Teigen, Beyonce and Jay-Z, and Oprah have all spent time in the Bluffs; film director Spike Lee also frequently vacations here, opting for coffee at Mocha Mott’s .

Today, Oak Bluffs still maintains a large African American community and is filled with myriad Black-owned businesses. Here’s where to start:

Founded by Elaine Cawley Weintraub and Carrie Camillo Tankard, The African American Heritage Trail of Martha’s Vineyard consists of 33 sites that collectively tell little-known stories about people of color on the island. You can wander the sites on your own, or join one of the trail's guided driving and walking tours, depending on your free time and mobility. (Note: tours only run during high season in the spring and summer.)

In the neighboring town of Edgartown, visit Martha’s Vineyard High School to see the artist Joe Murphy’s mural of Nancy Michael , a legendary Vineyard woman who was born enslaved. The work of longtime Vineyard resident and multimedia artist Janice Frame, an educator and contemporary artist, is on display at the Eisenhauer Gallery in Edgartown, too.

Where to eat

In Oak Bluffs, we have two main Black-owned faves. Winston’s Kitchen is a relatively new Black-owned business offering all sorts of fuel, from garlic chicken and roast turkey to mac ‘n’ cheese to stew beef stew. Biscuits is a popular choice for breakfast, as owners Chris Arcudi and Celeste Elser have perfected dishes like blackened shrimp and garlic-roasted red peppers (served over cheese grits or a cod cake), plus, of course, the restaurant’s namesake baked good.

Where to stay

The Oak Bluffs Inn , housed in a majestic Victorian home from 1870, was purchased by its third and current proprietors, Rhonda and Erik Albert, in 1998. Spike Lee has been a guest and the legendary jazz musician Wynton Marsalis once gave an impromptu concert in the living room. The inn is also within walking distance of the African American Heritage Trail.

Meanwhile, the Black-owned Inkwell Beach Cottage is one of several neighboring properties, including the Narragansett House (built in 1870) and the Dunmere By The Sea (built in 1883). Dunmere House, a new site on the African American Heritage Trail of Martha's Vineyard , was once listed in the Green Book; first published in 1936 by Victor Hugo Green, the book aided African American travelers seeking safe accommodations and places to dine throughout the United States.

This article was produced in partnership with TravelCoterie , a Black-owned publication featuring travel news, tips, and cultural experiences.

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How Martha’s Vineyard became a Black summertime sanctuary

For generations, forces worked to curtail Black freedom and joy. The Vineyard proved a safe place.

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Part of the Leisure Issue of The Highlight , our home for ambitious stories that explain our world.

The Inkwell, as one of Martha’s Vineyard’s famed beaches is known, stretches hardly 100 yards between jetties on the north shore of the island. To see it, it amounts to just a sliver of sand, but on a sunny day, the sea is vast and the precise color of jade, beckoning swimmers whose families have descended on the island in the summertime for generations.

Since the 1800s, Martha’s Vineyard (and the Inkwell) has been a renowned getaway for these Black families. The elite mingle with middle-class families on the island: Former President Barack Obama is rumored to have celebrated his birthday this month in his seven-bedroom mansion on Martha’s Vineyard. The island’s regulars over the years have included Henry Louis Gates Jr. and the late Vernon Jordan; Maya Angelou once described the town of Oak Bluffs, which includes Inkwell Beach, as “a safe place where we can go as we are and not be questioned.”

“I don’t have to catch my breath here,” says Skip Finley , an author and former broadcaster whose family has vacationed on the island for five generations. “It’s the freest place I’ve ever been.”

Vox sent photographer Philip Keith to Martha’s Vineyard, and to Oak Bluffs specifically, to capture the joy and community travelers find on the island today. The freedoms of Martha’s Vineyard highlight a truth about leisure in America: Lazy days in the sun, miles of coastline, and even the gut-churning and rickety climb up a monster roller coaster have not always been within the grasp of Black people.

Through the first half of the 20th century, segregationists masquerading as public officials across the country drew literal lines in the sand, parceling less desirable beaches to people of color; shunning Black children from public pools ; shuttering amusement parks to anyone but those with fair skin. Postal worker Victor H. Green penned The Negro Motorist Green-Book to guide African American travelers to safe, hospitable places, but the subtext was that the threat of violence could mar even the most benign of pursuits: For Black people in America, neither rest nor relaxation would come easily.

Among the safe spaces listed in The Green Book was Shearer Cottage, a Black-owned inn in the town of Oak Bluffs, on the north shore of Martha’s Vineyard.

Massachusetts was the first state to abolish slavery, and well-off African Americans had already built thriving lives and businesses in the state. “Martha’s Vineyard was part of the underground railroad, so it was known as a safe and welcoming community for African Americans,” says Nancy Gardella, executive director of Martha’s Vineyard Chamber of Commerce. “They didn’t feel entirely welcome in other beach enclaves.”

Along with the ferry that regularly deposited travelers right in Oak Bluffs, and the legions of Black families who began to visit beginning in the 1800s and then built dollhouse-like summer cottages in town, the inn helped spread word of Martha’s Vineyard’s comforts to families in Philadelphia; DC; Hartford, Connecticut; New York; and Boston.

More from the Leisure Issue

Finley, who for years authored a column about Oak Bluffs, estimates that during the offseason, there are only 700 black people who call Martha’s Vineyard home, and, he says, “most of us are retired.” In the summer, the numbers swell markedly, till, he guesses, 30 to 35 percent of the summertime population is people of color.

“That doesn’t mean that bigotry and discrimination doesn’t exist. Whatever happens in the world happens on Martha’s Vineyard,” says Gardella. At the time of The Green Book , few inns on the island accepted Black travelers, and the image of Martha’s Vineyard in popular culture remains one of whiteness and privilege.

But the reality challenges any notions of the island as an exclusive place.

On Martha’s Vineyard, “I can be who I want, when I want. Which is not necessarily true of the rest of the country,” says Finley. “When we get on a boat or plane to leave here, we call it ‘going to America.’”

Philip Keith is a photographer born and raised in Boston. He graduated from the Boston Arts Academy. His last assignment for the Highlight was photographing economist Emily Oster .

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• ‘An Overall Feeling of Joy’: How Martha’s Vineyard Became a Welcoming Oasis for Generations of Black Travelers

Black travelers have long felt at home on this Massachusetts island. Here's why—and a taste of what you can enjoy there today.

Tanvi chheda, tanvi chheda's most recent stories.

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Young children meet along Inkwell Beach and play together in the warm ocean spray. Soon after, their respective families become acquainted—and so begins a cherished summertime tradition.

In the Oak Bluffs area of Martha’s Vineyard, the Inkwell, as it’s fondly known, has long been a summer destination for Black families; the area was even listed in The Negro Motorist Green Book , a travel guide for vacation-bound African-American families popular from the ‘40s to ‘60s. It remains a favorite still today, and showcases a refreshing alternative narrative to the Black experience often depicted in mainstream media. Here, you’ll find Black travelers returning to a summertime haven generation after generation and forging bonds with one another.

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In recent decades, Martha’s Vineyard (and more specifically, Oak Bluffs) has also become known as a preferred getaway for the Black elite, with many prominent members of the community—from the late Maya Angelou and Oprah to Spike Lee and the Obamas—vacationing or buying homes here. Hollywood celebs such as Regina King and Jennifer Hudson have attended the annual Martha’s Vineyard African-American Film Festival, now in its 22 nd year. In popular culture, meanwhile, the destination has been showcased as a hub for wealthy Black families in movies such as The Wedding (starring Halle Berry) and Jumping the Broom (with Angela Bassett), and in TV shows like ABC’s Our Kind of People , produced by Lee Daniels.

Some of Oak Bluff’s historic gingerbread cottages, which were first owned by Black families  Courtesy P. Simon

Today’s thriving community has its roots in the fact that the island has long been considered a safe and welcoming place for vacationing Black families. But it’s hard to pinpoint what precisely makes it feel this way. Maybe it’s in part because Massachusetts was the first state to abolish slavery, or because of its isolated geography as an island, surmises Skip Finley , a prominent author, historian and former broadcasting executive and long time island resident.

“You can live your life here,” Finley remarks. “You can forget all those other characterizations. You don’t need that armor here on Martha’s Vineyard. Over in the rest of America, walking around the streets, making purchases, you have to be cognizant of fact that you’re Black. If you like fishing and you come to Martha’s Vineyard and you’re Black, that’s not going to be an issue.”

Black residents and visitors in the 1870s  Courtesy Martha's Vineyard Chamber of Commerce

The first Blacks to arrive to Martha’s Vineyard were actually indentured servants, whalers and domestic workers. On their days off, the women would come together in the enclave of Oak Bluffs, where some families eventually bought property when they could afford it. With each summer, more Blacks, from Boston, New York and other areas, began coming during the seasonal holidays.

Known as gingerbread houses for their colorful and pastel-hued exteriors, some of these historic homes in Oak Bluffs now operate as bed-and-breakfast-style inns, including the 10-room Oak Bluffs Inn and 14-room Narragansett House . The latter, operated by a family that’s been summering here across the generations, celebrates its multi-cultural, multi-racial heritage by hosting events such as “musical sundowners” and a series of “Inkwell Talks” led by noted authors, national magazine editors and prominent locals.

Spike Lee at the island’s African-American Film Festival  By M. Bossman

You’ll find more of these historic homes—like the Shearer Cottage, Dorothy West Home and Land Ladies—included on the Martha’s Vineyard African-American Heritage Trail , which comprises 35 sites of historic significance on the island that can be toured as a half-day excursion. The trail was started in 1998 by Dr. Elaine Weintraub, a history teacher, and Carrie Camillo Tankard, who both also worked to introduce more history about people of color at schools on Martha’s Vineyard.

In recent years, the duo has seen more interest in the trail from all communities, not only African-Americans, notes Camillo Tankard, who has lived on the island since 1967. “I wanted to leave a legacy for my children,” she adds, explaining the drive to research and create the trail. “There are many tours; people want to see the Kennedys’ properties. We feel it’s important to see the areas where Black people made contributions on the island, too.” (Reinforcing its historical significance, the community of Oak Bluffs is also recognized in a permanent exhibition titled “Power of Place” at the National Museum of African American History and Culture in Washington, DC.)

A multi-generational family gathering on the beach  By D. Welch

MV Escapes , a BIPOC-owned business specializing in concierge and event planning services, has also seen interest grow from a wide array of clients for everything from home rentals to private tours. For their clients, MV Escapes can arrange activities such as horseback riding and golf lessons, as well as help find the perfect vacation rental or coordinate a wedding or corporate retreat.

Co-founder Carol Bliss Furr agrees that the welcoming vibe is a major draw for locals and visitors. “We’ve had clients tell us they’ve never seen this type of environment,” she says. “Everyone comes, and everyone feels they can be a part of it.” Furr, who grew up coming to the island and then continued to bring her own kids, has been a year-round resident now for 11 years and counting. “It’s a safe place. It’s a place where kids can go and explore without feeling threatened by the outer world. They make lifelong friends.”

The Harbor View Hotel is a favorite of the Obamas.  Courtesy Harbor View Hotel

Furr confirms that the Inkwell is not to be missed, but one of her other picks for first time visitors is Chapoquoit Beach, known to locals as Chappy, located just across the Sound on the mainland. Back on the island, don’t miss the beautiful Mytoi Japanese-style gardens , she notes, plus high-end boutique Ethos for one of a kind women’s wear and BIPOC-owned C’est La Vie for gifts.

General manager Scott Little of Edgartown’s 117-room Harbor View hotel —a spot the Obamas are known to frequent that’s set in a recently renovated historic Victorian property—echoes a similar sentiment about the island. “The vast majority of people who come to Martha’s Vineyard, of all nationalities and colors, come because it’s a destination where they feel comfortable and that’s proactively welcoming,” Little says. “People don’t value riches here; they value privacy and non-judgment.”

Lennox & Harvey owners Mark Chung and Eric Coles  Courtesy Lennox & Harvey

Case in point: owners of Lennox & Harvey , Eric Coles and Mark Chung, who had been coming to the island during the summer for some 25 years. They finally moved here in 2017 and opened their highly curated modern take on a general store in nearby Vineyard Haven. Named after their grandfathers, who were creatives and design-minded in their own right, the much-buzzed-about store stocks men’s and women’s wear alongside finds like Japanese ikat fabric-woven wallets, Izipizi sunglasses and Alessi picnic baskets.

A taste of what’s on offer at the Outermost Inn  Courtesy Outermost Inn

Once they moved to the island full-time, Coles and Chung realized how tight knit it truly is. “It consists of a really strong community that looks out for each other in a way that only small towns, or certain neighborhoods within big cities, seem to do,” Coles shares.

To get a feel for that inclusive atmosphere, Coles and Chung suggest heading to one of their own favorites, Outermost Inn . “The island isn’t about formality, but the most ‘formal’ of all the restaurants would be Outermost Inn, not in the traditional sense but in that it’s often a special occasion restaurant,” Coles says. “It’s located at the most western point and the most remote part of the island in Aquinnah, formerly known as Gay Head.  Since it’s so far out for most people on the island, it’s generally a place to go to celebrate something. The view overlooking the ocean is spectacular, so go in time to see the sunset.”

A photo of Inkwell Beach swimmers from the Michael Johnson Photo Gallery  By Michael Johnson

Some of their other suggestions include Le Toile for classic French fare; Grey Barn & Farm , which offers cheese and charcuterie tastings in a beautifully restored barn; and Knowhere Gallery , in Oak Bluffs, for contemporary art. More art can be found at the Michael Johnson Photo Gallery , where Harlem-born photographer Johnson, who spends half the year on the island, showcases his signature photos of Inkwell Beach and its regular “polar bear” swimmers. One shot in particular stands out: a beautiful black-and-white image of a group of these intrepid swimmers in the water, their hands raised in the air. It’s an encapsulation of what Coles describes as the “overall feeling of joy” of being here—the same feeling that keeps visitors coming back.

Read More On:

• Black History Month
• Martha's Vineyard
• Massachusetts

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Whether you’re here for a day or longer, you want to be sure you don’t miss anything Martha’s Vineyard has to offer. Some of the easiest ways to do that is with a tour!

SIGHTSEEING TOURS

Tour buses and vans are located at the Steamship Terminals and most other incoming ferries and depart on regularly scheduled times May through October. Private passenger vans are also available for customized group tours, and step-on guides are available for your tour bus.

TOURS BY WATER

​Kayaking tours are a fun way to experience the Island by water. Kayaking tours are available for people of all ages by Island Spirit Kayak, the Felix Neck Wildlife Sanctuary, and by the Trustees of Reservations. Visitors may also wish to tour the waters of the Island by charter boat or with any number of great sailboat charters.

SELF GUIDED TOURS

Self-guided walking tours are easier than you think! By using the Island’s super simple and convenient public bus system, Vineyard Transit Authority, you can easily visit the three main port towns of Vineyard Haven, Oak Bluffs, and Edgartown. Simply take the #13 bus to and from each of these towns, and you’ll be let off at convenient, in-town locations. From there, you’re able to easily stroll the towns, shop, dine, and check out their points of interest at your own speed. The VTA busses run reliably and frequently, so there’s no need to worry about time! Check out their suggestion of how to see the island in one day using the public transportation. And if you’re not familiar with public transportation or haven’t ever used it, we assure you this couldn’t be easier.​

The African American Heritage Tour is a self-guided tour of sixteen historic sites that reflect the contributions made by people of African descent to the history and culture of Martha's Vineyard.

LIGHTHOUSE TOURS

Three of the five lighthouses on Martha’s Vineyard have grounds open to the public and easily accessible: Tours of the East Chop Lighthouse and Edgartown Lighthouse are available through the Martha's Vineyard Museum. Tours of The Gay Head Lighthouse are available through the town of Aquinnah. Cape Poge Lighthouse on the smaller island of Chappaquiddick is available to tour by contacting The Trustees of Reservation, which provides an over-the-sand ride in a 4-wheel vehicle to the lighthouse. One lighthouse, the West Chop Lighthouse, is run by the Coast Guard and isn’t open to the public, though it can be seen during a drive through West Chop, along with some other gorgeous views of the sea!

WALKING TOURS

Edgartown Tour Company offers a variety of walking tours including: Edgartown History Tour- A walking timeline of Martha's Vineyard. This tour focuses on history, architecture, whaling and ecology. And the hugely popular Amity Walking Tour, visit scenes from JAWS and discuss the production and impact of this classic film.

​Enjoy a truly unique Guided Birding Tour with the Island’s own Robert Culbert of Nature Watch, by calling 508-560-5294.

Looking for Whale Watching? We get asked this a lot! Unfortunately there is no whale watching in our waters! Because of the location of Martha’s Vineyard, with the Vineyard Sound as our northeast waterway, the Nantucket Sound as our northwest waterway, and the Elizabethan Islands in the Atlantic Ocean to our south, whales don’t enter our waters. Check out WHALETRAILMA.COM for a complete list of available whale watching locations.

5 things to do on Martha’s Vineyard

S even miles off the coast of Massachusetts is an island full of unspoiled landscape and plenty of fun, according to Carol Ward, information specialist for the Martha’s Vineyard Chamber of Commerce.

A New York Times best-selling author shares her favorite Martha’s Vineyard spots

Martha’s Vineyard, with 124 miles of coastline across six towns — Aquinnah, Chilmark, Edgartown, Oak Bluffs, Vineyard Haven, and West Tisbury — is a vacation destination with a year-round population of about 23,000 that balloons to 200,000 during the summer months, according to the chamber.

The Massachusetts escape has been called one of the most magical island getaways in the U.S. by Country Living and served as a backdrop for New York Times best-selling author E. Lockhart’s books. Boston.com readers recently named Edgartown the most picturesque small town in Massachusetts .

“It is a really, very, very unique place,” Ward said. “It’s a beautiful place on a very human scale that allows you to really connect with what you are seeing and what you are doing.”

The island’s diversity means visitors of all ages and interests can customize a day of fun, Ward said, by choosing from activities such as historic sites, shopping, dining, beaches, hiking, biking, museums, art galleries, farms, lighthouses, following the African American Heritage Trail , and more.

Whether strolling down island through bustling Oak Bluffs or visiting the unspoiled landscape up island at places such as the famous Aquinnah Cliffs , there’s a “sense of timelessness” on the island, Ward said.

“It’s just magic,” she said.

Ward offered the following tips for what to see and do during a day trip to Martha’s Vineyard this season.

1. Head to the Gingerbread Cottages

A neighborhood full of 19th-century “Gingerbread Cottages” is as well-known as the island’s beaches and lighthouses. The 318 pastel-colored homes are located at the  Martha’s Vineyard Camp Meeting Association , a National Historic Landmark.

“It’s lovely,” Ward said about the famous neighborhood.

The Tabernacle , located on the grounds, is the largest covered outdoor performance space on the island and hosts a sunset concert series in the summer. The cottages are privately owned, so visitors must stay on the public pathways.

“They do have a little museum that’s open in July and August where you can see what the inside of the cottages look like,” Ward said.

Summer visitors can also take guided walking tours of the neighborhood on Tuesdays and Thursdays during the months of July and August, and private tours are available by appointment.

2. Head to the beach

“Because we are an island, you are never very far from the beach ,” Ward said.

The island offers many beaches, some public and others reserved for residents and town visitors with a parking or beach permit.

Joseph Sylvia State Beach in Oak Bluffs, which runs along the eastern side of the island facing Nantucket Sound, is great for families due to its “gentle child-friendly waves,” according to Ward.

Katama Beach , also called South Beach, in Edgartown offers three miles of barrier beach on the south shore. The public beach is one of the island’s most popular ocean-facing beaches, Ward said, and vehicles with permits are allowed on marked trails.

For a more remote experience, Ward recommends heading to Menemsha Public Beach in Chilmark or Lobsterville Beach in Aquinnah.

Menemsha Public Beach, next to Menemsha Harbor, is popular for its sunsets, Ward said (author E. Lockhart called them “ magical “). Lobsterville Beach in Aquinnah offers two miles of Vineyard Sound beach and dunes and is a favorite fishing spot.

3. Explore a museum and view art

There are several fantastic museums on the island, according to Ward.

Martha’s Vineyard Museum in Vineyard Haven, just a 10-minute walk from the ferry terminal, houses more than 100,000 items, and current exhibits include “Unfreedom: Stories of enslavement, indenture, and incarceration on Martha’s Vineyard” and “Jaws: Creating Amity Island.” The movie “Jaws” was, of course, filmed on the island in 1974.

“It is very comprehensive,” Ward said about the museum. “It has a little area for kids and it really gives an overview of the island and how it has evolved over the years.”

The Carnegie Heritage Center in Edgartown is “a wonderful little gem of a museum,” Ward said. The restored landmark includes reading rooms, a gift shop, a library, and a revolving exhibition called “Living Landmarks.” Visitors can learn the history of the Wampanoag people at the Aquinnah Cultural Center .

Travelers can also walk through an outdoor sculpture garden in West Tisbury at The Field Gallery , Ward said, which features contemporary art by both emerging and established artists.

4. Enjoy dinner with a view

There are so many fabulous restaurants across the island, Ward said, and some serve up incredible waterfront views.

The Lookout Tavern in Oak Bluffs is a waterfront restaurant with a festive atmosphere and good food, Ward said. The restaurant, which does not take reservations, serves seafood, burgers, and sushi. It has a raw bar, too.

“It just puts you in that vacation frame of mind,” she said.

Bettini at the Harbor View Hotel on Edgartown Harbor and across from the Edgartown Lighthouse serves American cuisine with an “island farm-and-sea-to-table philosophy,” according to its website.

“It is an excellent place for dinner and has an excellent view,” Ward said.

The Dunes , a restaurant at Winnetu Oceanside Resort in Edgartown, recently named among the best family-friendly resorts in the U.S. by Tripadvisor, is also well worth dining at, Ward said.

“They have a wonderful deck,” Ward said. “The view is stunning. The grounds are stunning. The food is delicious. It’s really very special.”

During the summer months, guests can arrive at the restaurant via water taxi from downtown Edgartown.

5. Check out a farm — or a farmers market

A lot of Martha’s Vineyard is rural and the island’s many farms are great places to check out, Ward said.

Grey Barn & Farm is a certified organic farm, creamery, and bakery in Chilmark, which was established in 2009 and offers tours followed by cheese tastings in the garden.

“They have the most extraordinary cheese that they make in-house,” Ward said.

Another excellent island farm is Morning Glory Farm in Edgartown, Ward said, a family farm established in 1975 that grows 60 acres of vegetables and fruits and offers a farm stand and bakery.

“They do a great job with their baked goods and other things that they produce,” she said.

The West Tisbury Farmers Market , which has been feeding islanders since 1974, is open from June to October on Wednesdays and Saturdays from 9 a.m. to noon.

“That’s definitely something worth checking out,” Ward said.

Getting there

Travelers can get to Martha’s Vineyard by ferry or by plane.

“There’s something very magical about a ferry trip,” Ward said. “It is certainly part of the experience.”

Visitors can take the Steamship Authority , which is a year-round ferry service that also carries cars, or seasonal ferry service out of Hyannis, Falmouth, and New Bedford.

Once there, guests can take advantage of an all-island bus system that generates from Vineyard Haven, Ward said.

“You can take buses to other parts of the island, which is wonderful if you are here for a day trip and don’t have a vehicle,” she said. “You can easily pick up a bus to Oak Bluffs and Edgartown and West Tisbury, and from those points you can continue on to other parts of the island such as Aquinnah and Menemsha.”

Guests can also rent cars and bicycles for the day, and use a ride share service.

Reader recommendations:

Food and beverages:

Back Door Donuts — @kimaustinpowers

Larsen’s Fish Market — @noahvanschalkwyk

Nomans — @kerryemooney , @billykeane96

West Tisbury Farmers Market — @whattheheckner

Activities:

Aquinnah Cliffs — @bostown66 , @mandygrayy , @12numberkejoote

Beaches — @melissam.driscoll

Bicycling — @suzsen , @chrism051901 , @pallavikolambkar , @amacattack12

Edgartown shopping — @shophappy

Gay Head Lighthouse — @metal_head_ralfi_ralf

Lucy Vincent Beach — @cryandancebeast

Oak Bluffs — @addisonprimm

Old Sculpin Gallery — @sydcaroline

South Beach — @kbry2000 , @colleen_williams

Yoga on the Vine — @sydcaroline

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