09/09/2026
My cousin Veronica wanted to celebrate her milestone 75th birthday on Martha’s Vineyard. But she didn’t want a girls trip. She wanted a Sisters Trip. And there is a difference.
She wanted women connected through the many ways we define sisterhood. She is an AKA. I am a Delta, and I invited one of my Sorors. We had other AKAs and a Zeta among us. Some of us are also Links, Girl Friends and Jack & Jill Moms. And all of us are Sisters in Christ.
Ten women. Sisters.
So when Veronica (Ronnie) called me several months ago about the trip, I said yes before there was really even a question.
First, because Ronnie plans the BEST trips. And second, because she is pure joy to be around.
Ronnie handled everything. She found us a fabulous two-story, five-bedroom house with a separate basement apartment, arranged our transportation on the ferry and set up taxi service. And we got lucky with Franceska, our wonderful driver, who before long simply became another member of the group.
This was my first trip to Martha’s Vineyard. Our summer vacations were to Sanibel Island for many, many years. While I knew something about the Vineyard’s history, I didn’t fully understand what Oak Bluffs has meant to generations of Black Americans.
Black people had been coming to Martha’s Vineyard since the 1800s. But in 1912, during an era when Black Americans faced segregation and exclusion from hotels, beaches and vacation destinations across the country, Charles and Henrietta Shearer opened Shearer Cottage, the first Black-owned guest house on Martha’s Vineyard.
Along with Inkwell Beach, it helped anchor what became a thriving Black community in Oak Bluffs—a place where generations of Black families could vacation, own homes, gather, rest and simply be.
And over time, Oak Bluffs became something more.
It became a place where Black political, artistic, religious and intellectual life could flourish.
I knew the history. And I knew the names of those who vacationed there: Spike Lee, Oprah Winfrey, Jasmine Guy, Henry Louis Gates Jr., Lionel Richie and the Obamas. And long before them, Madam C.J. Walker, Paul Robeson, Dorothy West, Adam Clayton Powell Jr., Martin Luther King Jr. and others.
I knew all of that.
What I didn’t understand was the culture.
Now I do.
I was surprised by how many people from home spend part of their summers on the Vineyard. We ran into people almost as easily as we would walking around Short Pump here at home.
And I definitely did not understand that Oak Bluffs buzzes with members of the Divine Nine.
I arrived with absolutely NO Greek paraphernalia.
Rookie mistake.
I did, however, have one red-and-white outfit, so apparently my instincts were working.
I quickly corrected the rest with a trip to C’est La Vie for a Delta T-shirt and borrowed a Delta sweatshirt from my Soror. Because every time we encountered another Delta, there were greetings, hugs, conversations and connections.
Sisterhood.
That was the recurring theme of the entire trip.
We purposely scheduled our visit AFTER the African American Film Festival, Greek Week and Links on the Vineyard. We wanted to experience the island without the huge crowds and actually get to know the place.
And we did.
We ate our way around Oak Bluffs—dinner at Black Joy, Inkwell Beach Club and Lookout Tavern; lunch at MV Chowder Co. and Nancy’s; and, of course, dessert from the Back Door.
We walked the Inkwell. The two Michelles rode the famous Flying Horses Carousel. We met some of the Polar Bears at Inkwell Beach, although not one of us took the plunge.
We took the African American Heritage Trail tour through Edgartown and Oak Bluffs and learned the stories behind the places we were seeing. Our tour guide was a brotha who grew up on the island. He explained the differing opinions about the name Inkwell Beach. Much of the old guard rejects the name as derogatory, while younger generations have largely embraced it.
We looked across the pond toward the Obama property.
We were told that Spike Lee was on the island because his flag was flying—and that we might see him riding around on his bicycle wearing his orange helmet.
And then we walked out of Biscuits.
And there he was.
Bike.
Orange helmet.
Spike Lee.
He graciously invited us over for a couple of pictures after he finished his conversation.
Because apparently that’s just another day on Martha’s Vineyard.
By the end of our trip, the two Michelles and I decided to skip the ferry and fly off the island while our other seven Sisters continued on to Boston.
And now that I am home, I am glad we went when we did.
There has been a lot of conversation about whether the Vineyard—particularly Oak Bluffs—is changing.
Have the festivals become too big?
Are too many people coming simply to see and be seen?
Has a place that generations knew as a quiet summer refuge become a networking mecca?
Maybe.
I even heard stories about people arriving during the busiest weeks dressed more for South Beach than an affluent New England hideaway.
But that genie is probably out of the bottle.
The secret is no longer a secret.
What I learned, though, is that the other Martha’s Vineyard is still there.
You can still sit on a porch.
Walk through Oak Bluffs.
Meet people on the beach.
Learn the history.
Run into friends from home.
Make new ones.
And understand why Black families have returned to this little island generation after generation.
For more than a century, this was a place where Black people could exhale.
Where they could gather.
Where they could build community.
Where they could experience leisure and joy in a country that often made even those simple things difficult.
And perhaps that is what I appreciated most.
Tomorrow marks the end of the summer season. Most people will return home. Our organizations will come off their summer hiatuses. Meetings, responsibilities, calendars and regular life will begin again.
Just as they have for generations.
And somewhere along the way, people will start thinking about next summer.
Now I understand why.
It was my first trip to Martha’s Vineyard. It will not be my last, Lord willing.
But strangely, Oak Bluffs didn’t feel like someplace I had just discovered.
It felt like someplace I already belonged.
Maybe that is the real magic of the Vineyard.
We went there for Veronica’s 75th birthday.
We went as Sisters.
And we came home understanding a little more about why generations of Black people have found sisterhood, brotherhood, community, history, joy—and home—there.
Frankly Speaking,
Adrienne P. Whitaker