With its tranquil beaches, historic charm, and luxurious homes, Martha’s Vineyard has long been a beloved destination for vacationers seeking relaxation and cultural richness. For well-heeled Black families, the island holds an even deeper significance.
During the early 20th century, the town of Oak Bluffs became a beloved summer refuge for many at a time when much of the country was segregated.
In the decades since, Oak Bluffs and its world-renowned Inkwell Beach have been frequented by prominent families and become symbols of Black excellence and generational wealth.
Today, the Vineyard remains a haven for Black travelers, offering a rich blend of tradition, luxury, and community.
If you’ve ever considered summering in Martha’s Vineyard, this guide will provide you with tips to make your visit memorable.
The Harbor View Hotel | Image courtesy of the brand.
Your experience on Martha’s Vineyard starts with where you choose to stay. First-time visitors looking for a mix of comfort, heritage, and modern luxury should consider Oak Bluffs. Oak Bluffs is a hub of Black history and home to many of the Vineyard’s historic “gingerbread” cottages, perfect for your summer stay.
The Inn is a boutique bed-and-breakfast that provides a cozy, personalized experience in the heart of Oak Bluffs. Its central location makes it easy to explore local shops, restaurants, and beaches.
Located in Edgartown, this luxury property offers well-appointed quarters with sprawling ocean views, upscale dining, and quick access to beautiful beaches. It’s a great option if you’d prefer a more secluded, getaway that’s still close to key attractions.
Here’s where the heart of Martha’s Vineyard really shines. For a more personal experience of the island, consider booking one of the gorgeous vacation homes available on the island.
Properties boast everything from historic charm with private pools to outdoor spaces perfect for evening gatherings. The best places book up well in advance of the season, so plan to secure your rental as early as possible.
Wherever you stay, you’ll find that Martha’s Vineyard’s lodgings effortlessly combine rich history with luxurious, modern amenities.
Well-known Vineyard shop C’est La Vie. | Image courtesy of the brand.
Shopping on Martha’s Vineyard offers a unique blend of upscale boutiques, charming local shops, and artisan goods. The island’s shops provide opportunities to indulge in high-quality products and service, many of which are created by Black artisans and designers.
A chic boutique in Oak Bluffs that offers an eclectic mix of women’s fashion, accessories, and home goods. Known for its stylish apparel and jewelry, it’s perfect for curating your vacation wardrobe.
A Black-owned day spa perfect for keeping your summer glow. Visit for classic spa treatments like facials, mani/pedis, and more. Caleen’s is ideal for relaxing between beach days and parties.
This unique retailer, known as a modern general goods store, stocks a variety of stylish goods and sundries that appeal to the island crowd. Visit to find interesting tchotchkes for home and lifestyle.
Shopping on the Vineyard provides a balance of local craftsmanship and luxury. You can find everything from handmade art to ultraluxury brands.
Illumination Night | Image courtesy of the Martha’s Vineyard Times
Martha’s Vineyard is known for longstanding traditions that inspire a sense of connection and history. You’ll be spoiled for choice on your visit, especially if you plan to visit in August. Add these to your to-do, and watch your trip come alive with excitement.
No visit to Martha’s Vineyard is complete without a stop at the famous Inkwell Beach. Historically, it served as one of the few beaches where Black vacationers could swim during segregation.
Despite the negativity white Islanders associated with the name, it was quickly reclaimed and became a source of pride for Vineyard goers. Today, it’s a vibrant gathering spot for locals and tourists alike, especially during the summer.
If you’re lucky enough to visit in August, don’t miss this tradition, held in Oak Bluffs. The gingerbread cottages, a group of 318 historic homes known for their style and signature pastel colors, are adorned with colorful lanterns to light up the night sky.
It’s a magical event where history and festivity meet, and offer a picturesque view of the island’s charm.
Taking place in August, this film festival has grown into one of the most significant events on the Vineyard. Featuring works by Black filmmakers and discussions on race, culture, and artistry, it’s a must-attend for travelers who appreciate art and film.
Participating in these traditions will connect you to the island’s rich heritage while providing moments fit for the best vacation memories.
Farm Neck Golf Club | Image courtesy of the brand.
If you’re seeking to uncover Martha’s Vineyard’s lesser-known treasures, these hidden gems will elevate your trip. Whether you have a passion for nature or want to upgrade your game on the greens, there’s something for you to enjoy.
While the sunsets at the Inkwell are lovely, Menemsha, a tiny fishing village, offers one of the best sunset views on the island. Bring a bottle of wine, a few nibbles, and a blanket, and enjoy the peaceful ambiance with the small crowd of locals who gather to watch the sun sink into the horizon.
If you enjoy golfing, this semi-private course in Oak Bluffs offers gorgeous views of the water and some of the most well-maintained greens on the island.
Known to attract notable Black public figures, it’s an excellent place to indulge in a leisurely, yet upscale activity. A half-hour private lesson with an assistant club pro is only $70, so add it to your list of affordable Vineyard activities.
For a serene, nature-filled experience, visit this hidden botanical treasure. Polly Hill’s curated gardens and woodlands are perfect for a tranquil afternoon walk, offering a peaceful escape from the busier parts of the island.
Taking a detour from the tourist track will give you an opportunity to enjoy a bevy of island treasures usually only experienced by locals. Add a couple to your itinerary to enrich your time in this magical place.
Martha’s Vineyard is more than just a picturesque getaway—it’s a place where Black history, culture, and community thrive. You’ll find a welcoming atmosphere, luxury experiences, and deep cultural connections that make the Vineyard an exceptional destination. Its idyllic reverie is on everyone’s list, though, so start planning for next year now.
Ready for the Good Life?
Subscribe to our newsletter
and get your first issue
of the magazine on us.
This will close in 0 seconds
Leave a Reply
Want to join the discussion?Feel free to contribute!