Why Martha’s Vineyard In August Should Be On Your Travel List
Ralph Lauren nearly broke the internet last month when it dropped a special Spelman and Morehouse College capsule collection celebrating Martha’s Vineyard and Oak Bluffs. The crest blazers and cardigans, cozy cable-knit sweaters, and those iconic Polo bears dressed in Vineyard prep, complete with “Oak Bluffs” embroidery, were the moment we didn’t know we needed.
But the collection wasn’t just about adding custom pieces to our wardrobes as style lovers, HBCU fans, and alums. To many, the drop was a nod to a place and a moment that holds deep meaning for Black America.
RL’s curated capsule dropped just as our social media timelines started filling with ferry rides, beach panels, and sunset dinners. Well, at least mine is.
It’s giving full-on Martha’s Vineyard takeover, as it does every year.
Each August, many African Americans flock to the area in droves for what’s been described as our unofficial summer homecoming. From historic Oak Bluffs to the Inkwell Beach, it’s a place where history, culture, and community meet in the best way possible.
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Where Is Martha’s Vineyard & Why Are So Many Of Us Going There?
Martha’s Vineyard – an island off the coast of Massachusetts – has been a sanctuary for African Americans for over a century. In the early 1900s, Oak Bluffs was one of the few seaside towns where Black families could vacation freely despite segregation. In 1912, Charles and Henrietta Shearer opened Shearer Cottage. It was one of the first inns in New England to welcome Black guests, becoming a hub for writers, educators, and activists.
Even the beach has a story. Locals nicknamed the stretch where Black families swam “The Inkwell,” turning what was meant as a slight into a proud emblem of community and resilience.
As Maya Angelou said of Oak Bluffs: “It’s a safe place where we can go as we are and not be questioned.” That feeling still resonates today. Now, Black businesses thrive and so do other events and happenings.
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But Why Is August The Peak Time To Live Your Best Life In The Vineyard?
Like most moments in the culture, color-coordinated activities started being planned, and next thing you know, it became a trend. August is the peak season for the Vineyard’s Black cultural calendar.
HBCU Legacy Week brings alumni from historically Black colleges together for networking, day parties, and seaside brunches. The Martha’s Vineyard African American Film Festival showcases the best in Black filmmaking, drawing past attendees like Spike Lee, Ava DuVernay, Kerry Washington, and the Obamas.
And every morning, the Polar Bear Club keeps a 1940s tradition alive at the Inkwell. Early risers gathering for a refreshing 7 a.m. dip to start the day.
Calling All Bougie Babes To The Front – This Is For You
Martha’s Vineyard in August is rich auntie central. Whether you’re rich in wealth, relationships, time, or all three, here you can live your best life in style.
Picture morning walks along the water, rosé at lunch, and boutique browsing before an art show or jazz set. Kaftans, straw hats, high-waisted shorts, dark shades, and flowy dresses.
If this trip has been sitting in your group chat, let this be the sign. Lock Martha’s Vineyard in. From its deep roots as a safe haven to its current status as a luxury-meets-community getaway, Martha’s Vineyard in August offers something rare. Who wouldn’t want to be surrounded by history, culture, wine, curated events, and people who see you?
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