Why Martha’s Vineyard Matters

Martha’s Vineyard has been a summer sanctuary for generations of Black families. During segregation, when so many places remained closed to us, Oak Bluffs became one of the few spots in New England where African Americans could freely vacation, buy property, and build lasting community. Out of that history grew the iconic Inkwell Beach a gathering place that still carries deep cultural meaning today.

For many of us, the Vineyard represents something profound: legacy, tradition, and belonging. It’s where Black excellence and Black joy meet ocean breezes and small-town charm. It’s where history lives alongside modern-day traditions.

My Bucket List Dream

Visiting Martha’s Vineyard had been on my bucket list for years. Now, it’s become an annual tradition with my closest friends many of whom grew up vacationing there with their families, carrying on traditions I was just discovering.

Is it an easy trip? Not exactly. Between pricey rental homes, ferry logistics, and summer crowds, it takes real effort and planning. But it’s worth every single bit. Each August, my Spelman sisters and I make it work: two houses, our own bedrooms, a pool, and 20+ friends rotating in and out during the week.

And once I arrive? It’s pure peace. Martha’s Vineyard is the one place I allow myself to rest without guilt. I feel embraced, loved, and completely at ease every time I step off that ferry.

Planning Tip: Go with people who match your vibe. When costs are high, splitting housing with friends who understand the investment makes the dream trip not just doable, but magical.

When to Go

If you’re visiting in summer, August is the busiest time—and the most vibrant. The Martha’s Vineyard African American Film Festival brings in celebrities (yes, even the Obamas), plus a packed calendar of events, parties, and cultural moments. The trade-off? Crowds everywhere and long waits at restaurants.

If you’d prefer a quieter experience, try May, early June, or September. The weather is cooler, but the island feels calmer and easier to navigate. You’ll have space to breathe and really connect with the place.

Personally, I love August for the energy and traditions—there’s nothing like Vineyard energy in peak season. But I’m also planning an off-season trip, just for rest and reflection.

-----

Where to Eat

Food is seriously half the fun of the Vineyard. Some of my absolute favorites:

Atlantic – Right on the water, this is our first-night tradition. Calm waves lapping while you eat, incredible food, and that moment when vacation officially begins.

Lookout Tavern – Packed every single night, but their buttered lobster rolls are worth the wait. Honestly, they might be the best I’ve ever had in my life.

Atria – Perfect for big group dinners. We gather 20+ friends here every year for those long, laughter-filled dinners that become the stories we tell all year.

19 Raw Oysters – A newer spot I tried in Edgartown this year and absolutely loved. Fresh, vibrant, exactly what you want on an island.

Beyond restaurants, there are amazing local markets and bakeries. We always grab their quiches for big group breakfasts—it’s become part of our morning ritual.

How to Get There

Martha’s Vineyard is an island, so getting there requires some logistics. You can fly directly into the Vineyard, but most of us take what I call the “planes, trains, and automobiles” route:

1. Fly into Boston

2. Overnight in Boston while the “Boston crew” stocks up on essentials—snacks, paper goods, wine, water, first aid supplies. Island prices are significantly higher, so this saves both money and stress.

3. Drive about an hour to the Woods Hole Ferry terminal

4. Take the ferry (~45 minutes of pure anticipation)

5. Fly directly to the island

Important: Every passenger AND your car needs a separate ticket. Summer ferry reservations open in January, so book early or risk disappointment!

Once you drive off that ferry onto the island, the Vineyard energy hits you instantly. Everything slows down calmer, softer, more peaceful.

Where to Stay

Here’s the real talk: housing is expensive. Weekly rentals can run anywhere from $10,000 to $50,000 depending on size, location, and amenities. That’s exactly why most groups split the cost—it’s the only way to make it work.

A few things you need to know:

- Book a full year in advance, especially for August

- Most rentals are managed by local agents, not Airbnb

- Deposits are typically due 30 days after signing, with the balance due 2-3 months before arrival

- Respect the homes many are family properties passed down through generations. Hosts often leave sweet welcome baskets, and it’s important to care for their spaces like they’re your own

For smaller groups or couples, boutique hotels and inns are an option, but they book incredibly quickly in peak season.

Things to Do

There’s no shortage of ways to fill your Vineyard days:

Beaches

- Inkwell for its incredible history and community

- Menemsha for those breathtaking sunsets everyone talks about

- South Beach for wide-open waves and space to spread out

Towns to Explore

- Edgartown: Upscale shopping, amazing oysters, and classic New England charm

- Oak Bluffs: Vibrant, historic, and home of the legendary Inkwell

- Vineyard Haven: The ferry hub with cozy shops and great local eats

Events & Experiences

- The Martha’s Vineyard African American Film Festival in August

- Group BBQs that turn into all-day celebrations

- Live music floating through summer air

- Local art galleries and pop-up events

Everyday Joy

The real magic happens in the quiet moments: long brunches that stretch into afternoon, lazy pool days with no agenda, shopping local boutiques, and slowing down enough to actually breathe.

Why I Keep Going Back

For me, Martha’s Vineyard is so much more than a vacation destination. It’s where history, friendship, and healing all meet in one perfect place. It’s where I stop rushing, where rest feels natural instead of guilty, and where my soul finally exhales.

Each August, I get to recharge with my people the friends who’ve become family, the traditions that ground us, the laughter that carries us through the rest of the year. And now, I’m carving out time to visit off-season too, just me, the ocean, and the quiet that only islands can provide.

Final Thoughts

If you go, take time to learn the history, support the local community, and let yourself slow down. The island has a way of holding you if you let it.

Planning your first Vineyard trip? Drop your questions in the comments. I'll share what worked for us and what I'd do differently next time.