PVs: de-influencing your martha's vineyard trip (Part 1)
the legacy, cultural impact and context to decide whether to visit
Welcome to another edition of Pointed Views: a monthly deep dive into a topic we can’t stop thinking about and need to get off our chest. This week you’ve got Kristin (hiiiii) coming at you to talk about one of the true loves of her life: Martha’s Vineyard.
Like many other Black people that have found rest & community on the New England island, Martha’s Vineyard has become my comfort vacation spot. As we approach the glorious month of August, the time when the island hits peak activity, it felt right to dive into the people, places and things that make it so special. Martha’s Vineyard is still a relatively niche vacation destination, however, the recent onslaught of media attention, including last week’s Ralph Lauren for Oak Bluffs collection, is giving MV a new level of exposure that is both well-deserved and nuanced when it comes to protecting a place that has served as a sacred space for Black people over multiple generations. And, as someone who has visited Martha’s Vineyard the last 10 summers, I know this acutely. I was well aware of the rich history before my first visit so my anticipation was already high. But it never could have prepared me for the visceral reaction that hit me within seconds of breathing in the salty air. It was like my nervous system reset. Like I was joining a collective sigh of relaxation with every other Black person who felt allowed to just “be” amongst community that feels like extended family.
Now, the flip side of this, is that I also know that it’s not an easy place to navigate. I’ve both been a guest at others’ homes and hosted my own share house and there are several things I always tell my first-time visitors before they commit to manage their expectations. Even the pre-trip planning alone has de-influenced most people from following through. However, I believe every person that wants to visit and experience the magic of this place absolutely should, with one big asterisk*
*Like any destination, the island has cultivated a culture and community that is essential to its magic, so, as a visitor it’s imperative that you go into the space with this understanding and respect its locals and the energy that’s been created for the Black community.
If you’re still with me, let’s dive in. I’m pretty sure you’re about to be hooked.
A brief history lesson to explain what makes the culture & community so special
Okay students, class is in session. Because we can’t talk about the energetic perfection of Martha’s Vineyard without first touching on the history between Black Americans and the island’s cultural and social make up. Specifically in Oak Bluffs, our cultural epicenter of the island. It has served as a safe haven for Black Americans for generations and is filled with Black-owned homes and the iconic Inkwell Beach (side eye-ing that name, but yes, we’ve reclaimed it over the years). It’s importance can’t be overstated as a physical representation of generational wealth, legacy, community and rest – a true rarity for us in this country.
The history goes back to the late 1800s and early 1900s, when Martha’s Vineyard was one of the only places that Black Americans could vacation & buy property without being met with exclusion and segregation. And let’s be real, it was still America in the 1900s, while it may have been “easier” for Black people to gain access to homeownership, it was not easy. Shearer Cottage was vital in bringing exposure to the island as the first Black-owned inn in Martha’s Vineyard that was named in The Green Book and was part of the underground railroad. It was a literal safe place for Black Americans. As more people began to own homes and vacation in Martha’s Vineyard, the community grew and continued to attract affluent Black families & notable figures including Martin Luther King Jr, Harry Belafonte, Jessie Jackson, Adam Clayton Powell, Jr., W.E.B. Du Bois, and Henry Louis Gates Jr. Additionally, one of the reasons we are able to reflect on the deep history of the island is The Cottagers, Inc. an organization founded by Black women homeowners of the island dedicated to community advancement and historical preservation.
Fast forward to 2015 and my story with MV begins. What originally started as a mother-daughter trip between 11 friends that are family, eventually turned into an annual share house with friends bouncing between the weeks of July 4th and mid August, a decade of various experiences and stories shared. And I know so many of these memories will be the ones I’m talking about way into my 80s and 90s.
understanding its cultural impact
I love observing and studying shifts in pop culture, and we are living a cultural shift as it relates to Martha’s Vineyard. Pre-2000s, most people discovered Martha’s Vineyard through word of mouth. Someone’s aunt has a generational tie to the island who invites a friend who falls in love and makes it a summer tradition. Which is truly how so many prominent Black figures ended up visiting the island annually.
Then, Martha’s Vineyard started making a cameo in pop culture moments. Sure, Jaws was a thing, but in terms of media & culture representing the Black Experience of the island we had two classics The Inkwell in 1994 & Jumping the Broom in 2011 both set in MV. Then came the TV references and episodic specials mentioning the vineyard in Black-ish, Tyler Perry’s The Oval, Birth of a Nation, and more. Then, of course, we had music, notably Jay-Z’s mention of the vineyard in his 2002 classic “All Around the World".
What’s more interesting to me, though, is that the true rise of the island’s profile, I believe, happened through social media. Wait - social media has contributed to the exponential rise of a previously low-key vacation destination? Groundbreaking, I know. But it’s inarguably true. The access and ability to see into a more exclusive place sped up it’s cultural awareness in an exponential way. And then came The Obama Family summering in Martha’s Vineyard. The true impetus of not only cultural awareness but an overnight cultural stamp of approval. The island had become a topic of national conversation. From that point on, whether we want to admit it or not, it became cultural currency to say you were summering alongside the Obamas, maybe even catching a glimpse of them around town. Everyone had a story. My personal favorite was in 2018 when me and my friends were in a Soul Cycle death grip and by word of mouth found out the ONE CLASS we missed was the one where Michelle Obama graced everyone with her presence. Oh and we can’t forget Barack Obama’s epic 60th Birthday party in 2021. Bring back fine presidents please.
Fast forward to the post-covid, highly connected, parasocially warped world we live in and Martha’s Vineyard is being amplified by think-pieces, references and online conversations constantly across Instagram, TikTok, X, and Threads. In 2023, Bravo released Summer House: Martha’s Vineyard, which was met with mixed feelings upon its announcement and with even more mixed feelings from the general public when Bravo announced it was pausing the show in 2024. Earlier this year, Netflix mega hit Forever featured a viral episode depicting the protagonist’s family summering in the vineyard, something they did every year. IMO Forever painted an incredible and calming picture of the vineyard, that was very spot on in encapsulating the freedom, magic, community and culture that made me fall in love. And if the below scene isn’t goals, I’m not sure what is.
That brings us to this summer, where on the heels of Forever, Ralph Lauren released its Oak Bluffs collection in partnership with Morehouse and Spelman Colleges. In my house, we were excited about the collection. There’s me, who has summered on the vineyard for 10 years, and there’s my fiancé, a Morehouse alum, general RL fan and a Taurus (IYKYK). Money was spent. Morehouse album James Jeter was the Creative Director of the collection, which thoughtfully included multiple touch points, including this film, to dive deep into the heritage of Oak Bluffs and these HBCUs. Which, of course, led to discourse and contradictory opinions on the internet. Just how much discourse though is telling. It tells me that the profile of Martha’s Vineyard is at an all time high, right as we enter into the busiest season. We are about to see a ton of activity and August is the season’s peak. We’ve got the Martha’s Vineyard African American Film Festival (MVAAFF), which has huge names on board to host events and talk backs like Issa Rae, Tracee Ellis Ross, Michelle Obama & Craig Robinson, Teyana Taylor, Debbie Allen and more. And, this year, the MVAAFF signed a media partnership with The Cut (a Structured Chaos fav) which means a new level of coverage will come out of 2025 and beyond. On top of that, there’s a mini tech week, HBCU week, Greek week and more. I’d say it’s a safe bet that MV is about to takeover Black Tiktok for the next month.
time to de-influence you
you really wanna go, right? I know, I know. I hate to do it to you. But now that you’re hyped about the history and ready to experience the pop culture references first hand, it’s time to hit you with the hard truths. Let me caveat by saying despite it all, I’ve still chosen to go. For 10 years straight. Nothing great comes easy! Or whatever they say. I just feel a duty to share a list of no-BS things when considering a MV trip or building it into your annual summer plans.
It’s expensive!! This absolutely depends on where you live and how you choose to visit but generally, it’s $$$ that may not be “worth it” to you.
It requires long term planning (9-12 months) to do it right as well as research & effort if you’re hosting at a house.
This is not a Tulum / Ibiza / Turks turn up trip so if that’s what you’re looking for, keep it moving. Think more kickbacks & low key turn ups (like what we saw in Forever).
It requires commitment, by everyone involved. This is not the type of trip that accommodates a last minute add or drop in the group. If you’re in, you’re in.
Which brings me to my belief that you need a solid core group of friends or family to go with that you love. The vibes are more about your experiences and who you’re with vs. what you see and do. While the latter definitely help form your experiences, it always comes down to company, way more than most vacation destinations.
It’s a slow pace and small island, if you’re looking for sightseeing you’re going to be done in 2 days. May I suggest doing less a catching the vibe?
Tbh 80% of everything you can do in MV you can probably do in your city (or a short drive away). But again, it’s about the community & magic that makes even the ordinary so much more special.
Depending on where you’re coming from its not easy to get to! There are direct flights out of Boston, LGA, JFK and DC but depending on when you go you absolutely need a car, especially if you’re not staying in the Black cultural epicenter that is Oak Bluffs. Yes, you can call an Uber but in August expect to wait a minimum of 20-30 minutes to get one.
If you’re going for the clout, most of the social events are invite only / iykyk so I would recommend being quite connected to feel satisfied.
Vineyard trendspotting
At the end of the day, Structured Chaos is a newsletter dedicated to spotting/predicting/reporting cultural trends and curating recommendations based on them. So, here’s what we see coming:
A new era of Black tastemakers & figures owning homes and building generational legacy
The brands are coming. Expect more events & activations, which will mean more influencers. If you’re a brand person, authenticity is not a buzzword here - it is make or break. Do not try to fake it. We will know and we will talk about it. A safe bet? Tap into one of the notable figures with a generational legacy on the vineyard to get involved in your project.
MVAFF will become a required part of promo for key Black media & entertainment properties (as it should be!! and high key was pre-Covid & writers strike)
The pop culture references won’t stop but we expect to see more in music because it’s a space we haven’t seen too many references
Cyclical discourse across social media that pops up every year - people will be mad and happy for reasons none of us could imagine at this moment
More brand $$$ will be spent as sponsors or media partners (e.g. The Cut & HBO Max)
Bravo’s Summer House: Martha’s Vineyard is gonna come back. My guess is there will be a brand new cast to better encompass more of the island’s essence & history
Ok that was a lot!! And, guess what, I’m not done talking about it. Next week I’m hitting you with a Part 2 that gets veryyyy specific. A full Martha’s Vineyard gate-kept guide is coming your way. I’ll tell you when to go, how to know who to go with, how to find a place to stay, what to do when you get there and everything in between.
And, if anyone will be on the island in August, drop a comment! Would love to see you out there.
xoxox KT
Such a great a great read! And I’ll be there in OB!
Love this!!