Martha’s Vineyard is a picturesque summer getaway, but also a Black cultural landmark. When Black film and television creatives bring their characters there, they’re making a statement. On screen, Martha’s Vineyard becomes a symbol of Black wealth, of Black legacy, of ease, and of multigenerational presence. Whether it’s The Inkwell, Our Kind of People, or Netflix’s She’s Gotta Have It and Forever, the Vineyard is less about escape and more about the message: We belong there. We’ve been there.

According to the Martha’s Vineyard Chamber of Commerce, the first Black people arrived on the island as enslaved servants and indentured laborers. Over time, Oak Bluffs became a thriving seasonal home base for middle- and upper-class Black families from New York, D.C., and Boston. Places like Inkwell Beach, once named in mockery, were reclaimed as community landmarks. In 1912, Charles and Henrietta Shearer opened Shearer Cottage, one of the first lodging establishments to serve Black guests.

This stretch of island land holds collective history: the African American Heritage Trail marks dozens of significant cultural sites, from historic inns to burial grounds to the homes of literary legends like Dorothy West. Every corner of Oak Bluffs whispers legacy—and that legacy lives on in our films.

A cult classic directed by Matty Rich, The Inkwell follows Drew Tate (Larenz Tate), a teenager sent to Martha’s Vineyard in a late-1970s summer. His coming-of-age unfolds amid the affluent Black party scene on Inkwell Beach. The film highlights generational wealth and the tension between activism and respectability politics—all staged against the backdrop of Oak Bluffs. Though critically panned at first, it has become a cultural touchstone. For many, The Inkwell represents the first major depiction of Black Vineyard life on screen, capturing a specific aesthetic and emotional palette: sun-soaked leisure, teen angst, family politics, and that uniquely ’70s tension between revolution and tradition.

Inspired by Lawrence Otis Graham’s book, Our Kind of People dramatizes Oak Bluffs as a backdrop for Black elite society. It centers Angela Vaughn (Yaya DaCosta), a single mom launching a beauty empire in the land where her mother once worked. The show explores inheritance—both genetic and cultural—as Angela attempts to claim space in a world historically closed off to outsiders. Though short-lived, it used the Vineyard to interrogate what it means to belong—even among your own. The Oak Bluffs setting was loaded.

In Season 2, Episode 4 titled “#NationTime,” She’s Gotta Have It transports Nola Darling from Brooklyn to Martha’s Vineyard, setting the stage in Oak Bluffs as a place of artistic reconnection and self-discovery. Away from her usual world, Nola bonds with fellow creatives—including real-life artists Carrie Mae Weems and Amy Sherald—whose mentorship helps soothe her imposter syndrome. While there, she rekindles friendship with Dutch, a Pratt-educated peer, and meets Olu, sparking both flirtation and familial tension. “NationTime” turns the Vineyard into a crucible where Nola wrestles with belonging, art, and what it means to return home.

Created by Mara Brock Akil and loosely inspired by Judy Blume, Forever mostly takes place in L.A., but one key episode shifts to the Vineyard. That episode, informed by Brock Akil’s real-life ties to Oak Bluffs, becomes a narrative homecoming. In interviews, Brock Akil has emphasized how much the Vineyard means to her personally—how she wanted the episode to feel like a love letter to healing, especially for Black girls.

These portrayals offer a counter-narrative to whitewashed Vineyard imagery. Oak Bluffs remains a living, breathing community—one that reflects not only who we are but who we are becoming. The blend of old money, new voices, and generational storytellers creates a rich cultural mix that deserves its cinematic spotlight. When Black creatives bring their characters there, they honor that living history.

They say: We were here. We are here–and we’ll be here again next summer.

What’s Actually Happening on the Vineyard This Summer

As much as our film and television capture the cinematic energy of Martha’s Vineyard, the real island remains vibrant—and this summer, Black cultural life on Oak Bluffs and beyond is in full bloom.

Legacy Week (July 27–August 2) brings a powerful convergence of HBCU alumni, creatives, and professionals gathering for panels, brunches, and Polar Bear swims at the Inkwell. It’s not just networking—it’s ritual and reclamation rooted in history. Morning swims, sunrise yoga sessions on the sand, community conversations hosted by Stillpoint, and storytelling drop-in hours at the Oak Bluffs Library celebrate collective memory and mentorship.

Immediately following, from August 1–9, the Martha’s Vineyard African-American Film Festival (MVAAFF) takes center stage at the Martha’s Vineyard Performing Arts Center. Over nine days, independent and established Black filmmakers screen their work, participate in Director brunches, Women’s C‑Suite events, and even beachside White Parties. The festival has been an official qualifying event for the Oscars since 2018 and remains a beacon for Black storytelling on and off screen.

Close that same week, August 9 sees the lush Black Book Festival, featuring author panels, appetizers, readings, and bookstore pop-ups curated by Bunch of Grapes. It’s a literary celebration steeped in legacy and conversation among Black authors, luminaries, and readers alike.

Just before the curtain falls on summer, the Black Fashion Weekend sweeps into Union Chapel (August 13–17), spotlighting Black designers, runway showcases, and intimate industry mixers. Also on August 18, the Legacy Breakfast & Black History SWAG Symposium invites community leaders to Marlitas Museum for a Saturday morning brunch and gathering about history, identity, and purpose.

Martha’s Vineyard is a living archive of Black memory, joy, and presence. On screen, it gives our characters room to evolve. Off screen, it gives us space to gather, to rest, and to remember. With every return, we deepen the legacy.

Cover photo: We’ve Been Here: Martha’s Vineyard in Black Film, TV, and Real Life / Credit: Elizabeth Morris for Netflix