For Black people, we talk a lot about work.
We talk about sacrifice. Hustle. Excellence. Building something for our children. Breaking generational cycles. Creating legacy.
We don’t talk nearly enough about rest.
Not the kind of rest that comes when you are exhausted and your body finally forces you to stop. I mean intentional rest. Vacation. Laughter. Sitting near the water with nowhere you have to be. Spending money on an experience simply because you worked for it and want to enjoy it.
And I didn’t realize how much I needed to think about that until a girls’ trip took me to Oak Bluffs.
From Oak Cliff to Oak Bluffs
The title of this peice wasn’t mine.
During our trip, one of the women, Sydney, suggested that those of us connected to Oak Cliff take a picture together and caption it From Oak Cliff to Oak Bluffs.
I immediately loved it.
At the time, it was a clever caption. By the time I left Martha’s Vineyard, it felt like the title of a much bigger story.
I came to Martha’s Vineyard because a Black woman from Oak Cliff who has become one of my closest friends was celebrating another year of life. And she decided to celebrate by bringing together women from different parts of her world—different cities, different backgrounds, different personalities and different walks of life.
Initially, I thought I knew exactly what this trip was going to be.
A girls’ trip. Champagne. Good food. Pictures. Conversations that get progressively louder as the night goes on. A little foolishness and a lot of laughter.
And yes, there was plenty of that. But almost immediately, Oak Bluffs became something different for me. I had experienced this feeling once before while visiting Montgomery, Alabama. It is difficult to explain, but I knew it as soon as I felt it. It reminded me of walking through the doors of a church.
This is sacred space.
Not sacred because everyone there looked like me—they didn’t. I saw Black families. White families. Interracial couples. Groups of Black women traveling together. Older people. Younger people. People who appeared to have been coming to the Vineyard for decades and people, like me, experiencing it for the first time.
What struck me was the sense that all of us were occupying a place that understood the importance of its history. For generations of Black Americans, leisure wasn’t equally accessible. Where we could stay, swim, vacation and simply exist without the weight and threat of segregation was restricted. That history is part of what makes Oak Bluffs so significant.
Black people had been present on Martha’s Vineyard much earlier, but by the early 20th century Oak Bluffs was developing into an important African American resort community. In 1912, Charles and Henrietta Shearer opened Shearer Cottage, which became the first African American-owned guest house on Martha’s Vineyard. Along with the beach known as the Inkwell, it helped anchor a Black community whose cultural significance would stretch far beyond the island.
That is the history. Last week, I got to feel it.
A Place That Felt Familiar
Walking through the historic Martha’s Vineyard Camp Meeting Association (MVCMA) grounds, I found myself slowing down.
As I walked through those narrow paths and past those cottages, my mind kept traveling somewhere else. I could see people from another time.
I could imagine Black families leaving their homes dressed for church. I could imagine them returning afterward, changing clothes, gathering food and heading toward the beach. I imagined conversations on porches and children running around while adults laughed nearby.
It felt incredibly real.
There was an understanding there. The kind of code I think many of us recognize as Black people who have worked incredibly hard to obtain some measure of success. We understand what it costs. Many of us were raised to believe that success meant constantly proving that we deserved it. Work twice as hard. Be twice as prepared. Don’t get too comfortable. Don’t waste the opportunity. Keep going!
Those lessons helped generations of us survive and advance. But I also wonder whether part of breaking generational trauma is learning that we do not have to operate exclusively in survival mode.
Author and founder of The Nap Ministry Tricia Hersey has centered much of her work on that very idea. In Rest Is Resistance, she writes of the body itself as a place of liberation and rest as a means of imagining something different:
“Our bodies are a site of liberation. Naps are a portal to a new world.”
That idea stayed with me in Oak Bluffs.
Martha’s Vineyard can still sound elitist to many Black people.
There can be an assumption that this is where affluent Black people go to imitate a traditionally white version of wealth, access and exclusivity. That isn’t what I experienced in Oak Bluffs. Because maybe our definition of luxury should not only be measured by what we can acquire. Maybe luxury is also having the time to enjoy it. Maybe breaking a generational cycle isn’t only about working hard enough to give the next generation more. Maybe it’s also teaching them they are allowed to enjoy what generations before them worked so hard to make possible.
A Memory Waiting for Me
One morning at breakfast, my friends and I met an older Black woman from New Jersey. We started talking, as Black people have a way of doing when we encounter each other away from home.
She told me she had not been back to Martha’s Vineyard since 1979. Her daughter had encouraged her to return. She wanted her mother to come back and make memories again.
I almost cried right there at breakfast.
Because suddenly I wasn’t thinking about vacation. I was thinking about time.
I was looking at a Black woman returning almost half a century later to a place that held memories of who she had once been, now accompanied by the next generation encouraging her to make some more. Throughout the trip, we had versions of that interaction again and again. Black people we casually encountered became conversations. Conversations became stories. Stories somehow felt familiar. And eventually I understood the feeling I had been trying to name since arriving. I felt like I had been there before.
Not literally.
It felt more like I was experiencing a memory that had been left for me to pick up and continue.
Maybe that is what preservation is supposed to do. It allows one generation to leave enough behind that another generation can recognize itself when it arrives.
Oak Bluffs has been doing that for Black Americans for more than a century. The people who established businesses, bought homes, returned summer after summer and created community there weren’t simply taking vacations. They were establishing a tradition of Black belonging.
Last week, for a few days, we became part of it.
And yes, Oak Bluffs was a 10 out of 10. Even with my massive wasp bite. And my approximately 35 mosquito bites. That’s on me. The weather was so beautiful that I simply refused to go inside. But I came home with something much more important than bug bites and pictures.
I spend much of my life thinking about legacy through my work at Dallas Weekly—how I invest in my community, how I preserve something that existed before me and how I leave it stronger for whoever comes next.
Oak Bluffs reminded me that preservation has another side. We also have to preserve our joy. Our friendships. Our stories. Our ability to gather. Our willingness to rest.
The Gift I Didn’t Know I Was Receiving
That brings me back to the birthday girl. I wasn’t really sure what to give her.
She’s a lover of words, community and especially Black people, so eventually I realized that maybe the most appropriate gift I could give her was to write about what she gave me.
Sisterhood.
My Oak Cliff sister has a remarkable gift for connecting people. She is intelligent, passionate and intentional about uplifting our community in whatever capacity she can. I’m not even sure this was her intention with this trip. Maybe she simply wanted her closest friends together to celebrate her life. As she explained it, the women represented different walks of life and different pieces of who she is. But somewhere in bringing all of those pieces together, she created something else. She reminded me that legacy doesn’t always have to look like an institution.
Sometimes legacy looks like creating an experience another person will carry home.
So this is my birthday gift to my good sis, even though somehow I am the one who came home feeling like I received one.
Thank you for bringing me into your celebration of life. Thank you for the sisterhood. And thank you for reminding me that supporting Black people also means encouraging one another to stop working long enough to actually enjoy the lives we are working so hard to build.
From Oak Cliff to Oak Bluffs, Black people can do both.
We can work hard.
And we can rest well.
Until the next adventure.
With all my love… happy birthday, my good sis.
