It’s easy to paint a certain picture of Martha’s Vineyard if you’ve never been. Ahead of my first visit last month, I imagined what’s synonymous with most well-known islands: unspoiled beaches, freshly caught seafood, an unhurried pace of life. But I also imagined locals who were insular, conservative, and flashy with their wealth.

I was wrong about the people. Instead, I discovered residents who welcomed me into their homes and businesses that treated me like extended family. “There is a sense of community here that we’ve not experienced before,” says Eric Coles, a former New Yorker and co-owner of the chic modern-day general goods store Lennox & Harvey. “Because it’s a relatively small island, getting to know other people happens much easier and quicker.”

What else wasn’t I expecting? The Vineyard’s diversity, postcard-perfect beauty that extended way beyond the beaches, and how starkly different the bustling towns of down-island’s Vineyard Haven, Oak Bluffs and Edgartown feel from up-island’s Aquinnah, Chilmark, and West Tisbury.

Above all else, belying the island’s diminutive size is a vibrant culture and way of life uniquely its own. “It’s a less complicated world where you focus on the important things, like family and friends,” explains Winnetu Oceanside Resort’s general manager Matt Moore. “There is a reason Islanders playfully call the mainland America. Whatever happens there stays there, and whatever happens here is so much better.”

Ahead, eight reasons why you plan a summer vacation to Martha’s Vineyard.

Winnetu Oceanside Resort

For a stay that feels like worlds away from down-island’s summer crowds, yet at the same time close to popular attractions—South Beach is a breezy three-minute walk away—check into Edgartown’s Winnetu Oceanside Resort. The historic property spread across 11 scenic acres features 54 nautically-themed accommodations, a bevy of family-friendly activities from complimentary Children’s Day Programs to a scenic lawn for games—and beloved traditions like Wednesdsay clam bakes, cookies and lemonade, and antique fire truck rides.

For a terrific dinner wihout having to venture far, head up to The Dunes, where Chef Richard Doucette took over the reins last summer. Doucette is passionate about sourcing the best ingredients available—whether it’s creamy-sweet oysters from neighboring Katama Bay or North Carolina’s Lady Edison ham from pasture-raised hogs—and enlists simple, but thoughtful plating to let their best traits shine.

But it’s the familial service, which Moore describes it as “playful, personal, and welcoming,” that’s become Winnetu’s hallmark. I chuckled out loud when I read “What took you so long?” on Moore’s handwritten welcome note, and appreciated how the staff were more than comfortable going off-script. An assistant concierge, for example, drove me to Vineyard Haven, after learning I had pre-booked at a taxi to save me money. It’s evident these personal, spontanous gestures are beneficial for staff and resort guests, whom Moore refers to “as the secret sauce that makes Winnetu so special”—both happily return at a high rate season after season.

Lennox & Harvey

After working in New York City with fashion and home design’s most prominent names like Ralph Lauren and Herman Miller for years, partners in work and life Mark Chung and Eric Coles moved to Martha’s Vineyard for a change of scenery and careers. Opened in 2017 and located in Vineyard Haven, Lennox & Harvey—the names come from the couple’s grandfathers, both of whom were jazz musicians—offers a stylish curation of clothing, home goods, and other functional objects from all over the world to bring more joy into everyday moments today, and just as important, for years to come.

The Covington

First: reservations at this popular New American Edgartown spot are a must in the summer season. Second: begin the evening with the piping hot sweet potato rolls with garlicky butter. Third: cap off the night with a slice of the best-selling gooey and almond-studded honey pie. Last but not least: share everything in between bread and dessert, from the weekly rotating Farm Stand Salad to housemade pastas such as trenne smothered with shiitake ragu.

Beetlebung Farm

There’s an abundance of farms on the island selling everything from flowers to cheese, but if you only have time for one stop: make it Chilmark’s Beetlebung Farm. An incredibly diverse and flavorful variety of fruits and vegetables are grown on the six acres co-managed by Kate Woods and Nick Doherty (both are alums of New York’s Stone Barns Center) utilizing the principles of regenerative, no-till farming. Tomatoes, fennel, strawberries, and salad greens are especially superb this time of year.

East Beach

If vacationing in relative solitude if more your speed, hop on the little ferry from Edgartown over to Chappaquiddick (or Chappy, as the locals say). The island’s East Beach is pristine, peaceful, and the ideal spot to spend a day relaxing on the sand, swimming the calm waters, and walking with your dog.

Beach Road

Beach Road in Vineyard Haven is one of those rare eateries that feels just as fitting for a drop-in drink and bite at the bar as it does for a special meal to celebrate a special occasion. While the menu by Chef Frank Williams spotlights pristine seafood from local purveyors—the raw oyster selection is always spot on—there’s plenty of other hearty dishes to tuck into, like craggy fried chicken, herby lamb meatballs, and a fork-tender short rib. Save room for the butterscotch pudding.

Aquinnah Cliffs

Made infamous by Steven Spielberg’s Jaws, Aquinnah Cliffs is one of the Vineyard’s most iconic and picturesque destinations. Between the multiclored clay cliffs—picture shades of red, green, white, and black—and the spectacular sunsets, you’re guaranteed a kaleidoscope of dramatic hues. Feeling fancy-free? Then beeline over to Moshup Beach, where sunbathers cheerfully ditch their clothes.

Outermost Inn

Occupying Martha’s Vineyard’s westernmost tip, Outermost Inn pairs stunning vistas of rolling hills, leafy trees, and the rippling Atlantic with a $115 three-course prix fixe menu of elevated plates like lobster dumplings in dashi and duck confit accompanied by a crépinette and soubise. It’s one of the spendiest dinners on the island, but the welcoming atmosphere, warm hospitality, and breathaking setting justify the splurge.


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