August on Martha’s Vineyard: A month of Black brilliance, legacy, and joy

August on Martha’s Vineyard has always been more than summer vacation — it’s a season of cultural homecomings. A time when the Island’s shores hold not just vacationers, but visionaries. When porches hum with conversations about art, social justice, business endeavors, and family. When music and laughter spill out onto the streets, blending with the sound of the nearby ocean. It’s a month where so many Islanders and visitors gather year after year seeking the same thing: connection, joy, and the sacred affirmation of being seen. 

This summer’s lineup has been nothing short of extraordinary. August 1 kicked off the 23rd annual Martha’s Vineyard African American Film Festival, co-founded by Stephanie Tavares-Rance and Floyd Rance, which once again transformed Martha’s Vineyard into a cinematic sanctuary — one you can only truly understand if you’ve stood in the MVAAFF’s carefully curated space, felt the energy, and witnessed the magic unfold. Year after year, it becomes more than a festival; it becomes a fellowship, a gathering place where filmmakers, storytellers, and audiences breathe the same air of purpose and possibility. As Floyd once noted, “It’s always good to have somewhat of a convergence for folks of like mind in the arts and entertainment to gather, coalesce, share ideas, rekindle friendships and fellowship.” The caliber of voices and visionaries who grace this space is nothing short of monumental. This year’s gathering was a constellation of talent — Issa Rae, Jennifer Hudson, Dwyane Wade, Mara Brock Akil, Debbie Allen, and so many others — sharing space with emerging voices, each moment a reminder that the Vineyard is more than a backdrop; it is a sanctuary for Black creativity. The festival reached its peak on August 9, when former First Lady Michelle Obama herself closed the week with her powerful, undeniable presence — a moment that reminded us all of the weight and wonder of being in community.

That same energy spills seamlessly into HBCU Legacy Week, where the bond of historically Black colleges and universities takes center stage. It’s a celebration layered with fireside chats, beachside yoga, concerts, and the unmistakable pride that rises when we gather to honor our roots. At the center of it all is Sheryl Wesley, the founder, whose spirit could power the whole week on its own. Every August, she arrives ready to connect, laugh, and soak in the island with her people. She’s the life of the party in the truest sense. People love the space she has been curating, not just because of the events themselves, but because she fills them with warmth, a sense of being welcomed, and a kind of joy that feels contagious. Wesley reminds us, “What [HBCU Legacy Week] has done is illuminate what we’ve already been doing here for years.” 

Within that larger heartbeat comes Bison on the Vineyard, the Howard University homecoming away from home. As a proud HBCU graduate by way of the Howard University School of Business MBA program, I am moved beyond words to see so many of my people gather here on the very shores I call home. There’s something almost poetic about it: Mecca meeting the Vineyard, one sacred place unfolding into another. When we are here together, the island itself becomes an extension of Howard’s yard — full of pride, possibility, and that unshakable bond only we understand. And it’s not just Howard; you can feel the entire spectrum of HBCU camaraderie alive in Oak Bluffs. At any given moment — you’re surrounded by a sea of school colors, chants, and shared pride that remind us who we are and where we come from.

This HBCU presence isn’t new — it has been woven into the island’s fabric for decades. Generations of graduates have walked these beaches, held cookouts on these lawns, and carried the spirit of their alma maters into every corner of Island life. It’s a lineage of leadership, scholarship, and joy that needs no outside validation — but still, even the wider world is taking notice. This summer, iconic designer Ralph Lauren released a collection inspired by Oak Bluffs, and touched the edges of this legacy. Because truthfully, how could anyone look at the excellence that gathers here every August and not be moved? On Martha’s Vineyard, HBCU pride is more than a week on the calendar; it is a living homecoming, rooted in who we are and the futures we’re building. And every time we come together here, we remind the Island, and the world, that this legacy is not only alive — it’s thriving.

M.V. Soul Fest is pure celebration: music, movement, and moments that set the Island alive with rhythm. It’s the sound of joy and resilience, where both performers and audiences pour into a space that feels like culture and community in perfect harmony. The vision came from founders Stephen Anglin and David Van Allen, two cultural architects whose roots in Martha’s Vineyard’s music culture run deep. What began as backyard barbecues, jam sessions on the beach, and gatherings that centered art and fellowship has blossomed into something much bigger. In 2008, they planted the seeds of what would grow into M.V. Soul Fest. By 2022, that spark became a two-week festival that now stands as a cornerstone of the summer, anchored in soul, R and B, comedy, spoken word, and the undeniable vibrancy of Black culture. But M.V. Soul Fest is more than a stage or a schedule. It’s a movement, a homecoming, and a love letter to our community. Or as the festival’s own mission states, it is “the Soul of Summer” — a gathering that honors the past, celebrates the present, and inspires the future of soulful artistry on the Vineyard.

The second annual Black Brand Bazaar is a pop-up marketplace where creativity becomes commerce and culture becomes community. Hosted at the Dragonfly House in Oak Bluffs, this trunk show brings handcrafted artistry into the heart of the Island. Born from purposeful intention and collaboration — Awet New York, RAISEfashion, and the DJ Henry Dream Fund — the event united designers from across the U.S., as far away as California. This year’s lineup showcased the work of Aisling Camps, Awet New York, bySharisse (my personal fashion design and production brand), Studio Danroy, DLSH Creations, Gwen Beloti, Harbison Studio, House of Aama, Yesaet, and more. It was an exclusive experience that felt less like shopping and more like communion: Each piece was threaded with place, heritage, and hope. The spirit of giving and empowerment was especially tangible with the bazaar’s partnership with the DJ Henry Dream Fund. A portion of the proceeds supported this nonprofit’s mission to provide community-based scholarships, ensuring that youth can participate in sports, performing arts, and summer programs, even when financial barriers get in the way. As Angella Henry, co‑founder of the fund, puts it, “Turning a season of no into a summer of YES for so many is a core part of our mission to serve in the memory of DJ.” Each designer brought vision, narrative, and style to the Island stage. For those who shopped, and those who watched, it was far more than browsing—it was communion. Commerce, after all, can become community when Black artistry is both product and poetry.

Amid all this depth and heritage, one radical act of joy rose center stage: the Martha’s Vineyard Comedy Fest. Here, laughter isn’t just entertainment, it’s resistance, restoration, and radical joy embodied. Founder Steve Capers has long believed in the healing power of humor. His vision has always been clear: a “vibrant celebration of African American humor … a cultural celebration and a testament to the healing power of laughter, nourishing the mind, body, and soul with every show.” The historic Strand Theatre in Oak Bluffs served as the perfect stage: a community landmark whose walls have carried decades of memory, now echoing with comedy that uplifts and unites. The story of how it all began is Vineyard history in itself: In 2009, while vacationing on the Island and spending a day at the famed Inkwell Beach, Capers’ wife Dorothy encouraged him to follow through on his idea of producing a comedy festival centered on African American comics. At first, he worried it would be too costly to bring “big name” comedians to the Island. But with HBO stepping in as a sponsor, the vision became reality. For the past 14 years, some of the world’s most beloved comics have graced the stage, each year building on the last, the festival growing bigger, sharper, and more electric. And this year, in a moment that left the crowd buzzing, Capers announced with excitement, “Look who showed up at our 14th annual Martha’s Vineyard Comedy Fest to do a guest spot. The one and only Dave Chappelle!” What began as a single summer showcase has since grown into a beloved tradition. Fourteen years later, the Martha’s Vineyard Comedy Fest continues to prove that laughter is more than a release, it is survival, restoration, and yes, legacy.

The Strand opened its doors days later to another legacy-making moment: the Parent Matterz Youth Empowerment and Opportunity Expo. On August 12, more than 300 registered guests, including students from the Boston Boys & Girls Club, filled the historic theater for the third annual Martha’s Vineyard Youth Empowerment and Opportunity Expo. The daylong event, led by Rhona Vega, chief dreamer and founder of exposure and opportunities for Parent Matterz, created a space where young people could see what’s possible, and connect directly to pathways for their futures. Through interactive panels, vendor exhibits, and one-on-one conversations with professionals across industries, students explored opportunities in college prep, scholarships, internships, and careers. One of the day’s most inspiring highlights was the presence of Queen Kamora Freeland, the youngest Black female pilot in America, who attended with her family. Alongside her mentors — three accomplished pilots from the New York Metro Black Pilots of America, who flew their planes in for the occasion — Kamora reminded the students in the audience that the sky is truly not the limit. “This expo is about showing every young person — whether they live here on the Island, are visiting on vacation, or come from Boston — that their dreams are valid and achievable,” Vega said. Her words reflected the initiative’s guiding belief: “Youth can’t be what they can’t see.” With the support of co-organizer Taliah Givens of Given To Serve and a growing network of mentors, educators, and community leaders, the expo has become a cornerstone of August, positioning the Vineyard not only as a place of beauty but as a launchpad for opportunity. And that theme of opportunity and visibility carried forward to the next day at the historic Union Chapel, where the National Association of Black Journalists (NABJ) gathered for its 50th anniversary. Just as Parent Matterz showed young people the pathways to dream, NABJ reminded us all of the responsibility to protect truth, amplify voices, and safeguard the stories of our community in an era where journalism itself is under threat.

The National Association of Black Journalists (NABJ) returned to Martha’s Vineyard for its 50th anniversary, bringing another necessary conversation to the Island. Held at the historic Union Chapel in Oak Bluffs, the sanctuary was filled with community members eager to take part in the larger dialogue shaping our nation. The panel “Guardians for Truth: Protecting America’s Fourth Estate in an Era of Crisis,” could not have been more timely. The lineup was powerful: Charles Blow (New York Times columnist), Linsey Davis (ABC weekend anchor), Eugene Daniels (MSNBC), and Akayla Gardner (White House correspondent, Bloomberg), with the discussion moderated by Kim Godwin, former president of ABC News. Each panelist brought clarity, conviction, and urgency to the conversation, but it was Charles Blow’s words that reverberated through the room: “If we don’t stay in journalism, it negatively affects our community — we believe in the promise, telling the stories of those who cannot tell their own.” This gathering felt less like a panel and more like a call to action. Journalism, especially in its truest form, is in a state of emergency; it faces economic pressures, diminishing trust, and battles against disinformation. The very institution meant to serve as democracy’s watchdog is under threat, and when journalism dies, so too do the visibility and voice of marginalized communities. That is why having NABJ on the Island is so impactful. Their presence at this cultural crossroads doesn’t just amplify national conversations; it roots them in community. In a place long known as a sanctuary for Black voices, NABJ reminded us that our collective truth-telling remains both urgent and sacred.

The Vineyard Icon Awards brought a moment of collective recognition to all who contributed to the amazing month of August and beyond — shining a well-deserved spotlight on leaders, artists, and visionaries whose impact stretches far past our shores. It was a night marked by gratitude and reverence, honoring trailblazers who have pierced ceilings, told deeper stories, and inspired us all to keep moving forward. At the heart of this celebration was Erin Goldson, the visionary behind the awards. 

Erin’s love for the Island runs deep. Five generations of her family have called Martha’s Vineyard home; it’s a place where her roots and purpose beautifully intertwine. Addressing audiences gathered at Farm Neck Golf Club, she reflected that although she had attended many wonderful events on the Vineyard over the years, something was missing: an event that honored the people — the very heartbeat of the Island. “The Vineyard is a very special place for our family… For many in this room, it is their happy place,” she said. With that truth, the Vineyard Icon Awards were born, rooted in legacy, grounded in gratitude, and committed to giving back to the next generation. The inaugural honorees embodied the spirit of the Island and the mandate of the awards: music executive Troy Carter, film festival founders Stephanie and Floyd Rance, McKinsey senior partner Shelley Stewart III, former Atlanta mayor Keisha Lance Bottoms, and documentary filmmaker Dawn Porter. Their selection mirrored Erin’s ambition: to honor legacy, tell our stories, and shine light on those whose footprints resonate far beyond the Vineyard. Looking out over that luminous evening, you could feel the weight of it all: memory and purpose, gratitude and possibility, Island and legacy — all converging in one shared moment.

And as August carried us forward, it felt only right that this season and editorial would close with HistoryMakers. Founded by Julieanna Richardson in 1999, HistoryMakers has grown into the nation’s largest African American oral history archive, preserving the voices and legacies of Black leaders, artists, educators, politicians, and visionaries across every field. Julieanna’s mission is both simple and profound: to ensure that our stories, too often overlooked or erased, are documented, studied, and uplifted for generations to come. For me, this event carried personal weight. My grandmother was herself a HistoryMaker, her life and contributions woven into that living archive of excellence and resilience. To sit in a room that honored her alongside so many others was more than an event; it was an affirmation of legacy. It reminded me that the stories we inherit and the stories we live are part of the same continuum. As Richardson has often said, “We are creating an archive that will educate not just this generation, but generations yet unborn.” To have the HistoryMakers close out August on the Vineyard felt like the perfect punctuation to a month dedicated to legacy, joy, and connection. 

The events mentioned in this piece are just a few of many that go on in August. These events keep the Island buzzing with art, advocacy, music, and entrepreneurship — proof that our excellence takes many forms.

August here is not just a month, it’s a movement. From the red carpets of the M.V. African American Film Festival to the chants and reunions of HBCU Legacy Week and Bison on the Vineyard; from the rolling laughter that shook the Strand Theatre at the Comedy Fest to the youth empowerment of Parent Matterz that turned that same stage into a launchpad for dreams; from the urgent truths shared at NABJ inside Union Chapel to the music and rhythm of Soul Fest; from the artistry and commerce woven into the Black Brand Bazaar to the reverence of the Vineyard Icon Awards, and finally to the timeless preservation of legacy with the HistoryMakers: The Vineyard became something more than an island this August. It became a sanctuary of culture, history, and joy. This is the kind of summer that reminds us why community matters, why our stories matter, and why we must continue to create spaces where we can see ourselves fully — onscreen, onstage, in history, and in each other’s eyes.