In Black America during the summer, there are some guarantees we can (almost) universally agree on: We’re getting invited to at least one all-white event, we respect that the cookout potato salad making is strictly for vets and August in Martha’s Vineyard belongs to us.

When it comes to the latter, the chatter online becomes louder every year. Some of us have families who have “summered” in Martha’s Vineyard for multiple generations while others are excited to visit for the first time this August. Whether you and yours regularly rub elbows with The Obamas and other high-profile names or stay low key and off the radar, there’s one aspect of this cultural phenomenon that is not discussed enough. That is the importance of who is behind the fanfare that make Martha’s Vineyard the magical place it is all year long.

Martha’s Vineyard insider India Rose has entered the chat. This prominent real estate agent, social justice advocate, Martha’s Vineyard Black Owned Business Directory founder and mom spoke exclusively to ESSENCE about the ways her beloved home is not merely a vacation destination for the bougie and well-off, the importance of supporting Black-owned businesses and thoughtfully engaging with locals year-round and the value of community to the Martha’s Vineyard charm we have collectively come to treasure.

ESSENCE: Where are you from and what was your background before real estate?
INDIA ROSE: I’m a life-long Island resident. I was born in New Bedford, Massachusetts. My parents moved us to live on the Vineyard when I was about 10 years-old, entering the fifth grade. Before entering real estate, I spent my career in nonprofit leadership, serving in executive director and development roles where I focused on fundraising, partnerships, and community impact. Simultaneously, I was building my own businesses, including what is now India Rose Collective.

ESSENCE: Many people assume Martha’s Vineyard is purely a destination for “bougie” Black people.
ROSE: I think that’s one of the biggest misconceptions about Martha’s Vineyard. The headlines often focus on celebrity sightings, political figures, and high-profile events because those stories attract attention. But that’s only one chapter of the Vineyard’s story. 

There are teachers, artists, fishermen, healthcare workers, retirees, young families, and generations of Black families who have built traditions here for decades. Yes, Martha’s Vineyard can be expensive. That’s a reality of island life. But what keeps people coming back isn’t status. It’s community. Reconnecting with family, friends, and strengthening your relationship with yourself. Those are things that money can’t buy.

ESSENCE: August is also Black Business Month! When and how did you establish India Rose?
ROSE: India Rose Collective was born from a realization that my business and my career had evolved. My apparel and sports brands, Sideline and MV Streetwear, primarily serve seasonal visitors. My work in real estate played a large role in my pivot. I wanted to create a beautiful, elevated gathering place that also served the people who live here year-round. Today, India Rose Collective is equal parts boutique, gathering space, coffee bar, and celebration of thoughtful living.

ESSENCE: What are common misconceptions Martha’s Vineyard visitors have about the Black community who lives there year-round?
ROSE: 1) That Black people don’t live here, they just vacation here.

2) Everyone who lives here is wealthy. The perception that the island is only home to people with significant wealth is not only untrue it erases MV’s deep history as a place where working class Black people were able to come work and build communities. The median income on MV is around $65,000 which means just like most places around the nation, there are residents working to make ends meet and some experiencing poverty and housing instability. 3) Year-round residents exist to serve tourists. Many of us own businesses, lead nonprofits, work in public service, raise families, and contribute to the island every day of the year. August may be busy, but our lives don’t begin and end with the summer season. 

ESSENCE: What Black-owned businesses are a must-visit on the Vineyard?

ROSE: One of the best ways to discover Black-owned businesses is through the Martha’s Vineyard Black-Owned Business Directory, which I founded to make it easier for visitors to intentionally support local entrepreneurs.

My Must Visits:

India Rose Collective for an extraordinary retail and coffee experience.

Vineyard Caribbean Cuisine for the best oxtail and Jamaican beef patties.

Cest’ La Vie for Divine 9 licensed gear.

The Mariposa Museum to experience amazing Black artists and creatives.

African American Heritage Trail: Take the Black Business Tour or the Oak Bluffs History tour for a better understanding of our history, to where we are today.

ESSENCE: What about must-do MV events and activities in August?
ROSE: August is magical because there’s something for everyone. If you love fashion, Black Fashion Weekend celebrates creativity, entrepreneurship, and connection. If you’re a music lover, the Martha’s Vineyard Jazz Experience and the Martha’s Vineyard Comedy Festival showcase incredible talent while bringing people together. For families, the Flying Horses Carousel is a rite of passage. I rode it as a child, and later my own children did too.

I also encourage visitors not to over-schedule every minute. Some of the best Vineyard memories happen when you go with the flow. Watch the sunset, strike up a conversation with a local, spend an afternoon at the beach, or wake up early enough to experience the Polar Bears morning swim. The Vineyard reveals itself best when you leave a little room for discovery.

ESSENCE: Beyond August when are some other good times to visit MV?
ROSE: While August gets the headlines, September is when many locals fall back in love with the island. The weather is still beautiful, the ocean is warm, restaurants are still open, and everything feels a little more relaxed. June has also become an incredibly meaningful time to visit, especially around Juneteenth, as more conversations, programming, and celebrations highlight the rich Black history of Martha’s Vineyard.

If you’ve never experienced the Vineyard during the holidays, you’re missing one of its best-kept secrets. The twinkle lights, small-town traditions, holiday strolls, and quiet beauty create an entirely different kind of magic. Truly my favorite time of the year.

ESSENCE: What can Black visitors do to support MV Black locals during their vacations?
ROSE: Support doesn’t end with making a purchase. Of course, shop at Black-owned businesses, eat at Black-owned restaurants, and book Black-owned services. But also learn about the people behind those businesses. Visit local museums, support nonprofit organizations that are working to care for the vulnerable on the island, attend community events, and take time to understand the history that makes this place so special.

One of the greatest gifts visitors can give is respect for the community that exists long after summer ends. The people serving your coffee, creating your meals, or welcoming you into their businesses are also raising families, volunteering, coaching youth sports, and helping shape the future of this island.