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Martha’s Vineyard has a skunk problem. For generations, locals have sworn the animals are a non-native pest. But then how did they get there? Some blame longtime Vineyard Haven resident Craig Kingsbury, who was old enough to remember when the northernmost town on the island went by Tisbury. According to legend, Kingsbury set two unscented skunks—one male and one female—free to roam with the other animals on his farm. To his dying day, Kingsbury maintained his innocence, even though after he passed, his daughter, Trina, told the Cape Cod Times that he was in fact the guilty party. Can you really trace every skunk on the island to one man? Unlike the black-and-white mammal, on this island, as in life, the truth always seems to hover somewhere in the gray.

The gingerbread houses of Oak Bluffs.

The gingerbread houses of Oak Bluffs.

Legends, myths, tall tales: The Vineyard has it all. It’s the American ethos distilled into a rocky, triangular landmass just a short boat ride from Cape Cod. Case in point: Kingsbury wasn’t just a farmhand; he was a longshoreman, fisherman and actor, too. He’s credited with helping Robert Shaw become the crusty shark hunter Quint in Jaws, a character that was in many ways modeled after the salty, expletive-prone Kingsbury. Or so the story goes. (To my eye, Quint even looked like Kingsbury.) For an island export, you can do a lot worse than Jaws—a gripping thriller that still lurks in people’s minds as they bob in the waves. Not only was the movie primarily shot on location on Martha’s Vineyard, but the director, Steven Spielberg, pushed the verisimilitude so far that he used many of the locals as extras. You know the rest. The movie was a smash hit, which helped bring another invasive species to the Vineyard’s shores: tourists.

That includes yours truly. Like the rest of the summer flock, my family has been making a pilgrimage to the Vineyard whenever we can. It’s an extremely northeastern thing to do, the same way Fire Island and Block Island have their devotees. Martha’s Vineyard shares a similar identity with those summer destinations, but a long history of affluence and congeniality, detachment and isolation exist here. That’s partly evinced by the architecture, from the Victorian “gingerbread” cottages of Oak Bluffs to the Old Whaling Church built by shipwrights in Edgartown. No matter the island, there’s an easy-going romanticism that’s typically associated with island life. Such a feeling led former President Barack Obama, who just bought a $14.85 million estate on the island, to call it, “One of those magical places where people of all different walks of life come together; where they take each other at face value.”

That might be true, but there’s something darker at work too. At times, one can’t help but feel as if the island has the barbs of gravitas harpooned into its flank. Maybe it has something to do with the old graveyards lined with headstones—placeholders for the men lost at sea. Or maybe it’s the documented cases of depression, alcoholism, drug abuse and domestic violence that tend to spike in the winter months, when the population drops precipitously from 115,000 to 15,000 year-round residents. Or maybe the baggage is all my own: Martha’s Vineyard almost took my life, provided me with a job and bore witness to the dissolution of my last relationship. It’s also a place where, when some locals leave, they don’t say they’re going to Massachusetts. They say they’re going to America.


Recently, a Midwestern friend asked, with only a hint of irony, if Martha’s Vineyard was named after the cooking empress and one-time white collar felon Martha Stewart. “You know, that Martha?” she asked. In her defense, she had never been. New England’s surprisingly multiethnic coastal jewel, which draws unpretentious families and pastel-wearing patricians in equal measure, is named for anyone but Stewart. Far older than today’s American royalty, Martha’s Vineyard was named after an early 17th century founder’s daughter or mother-in-law: no one knows. It’s an etymological mystery reverberating through history, which sounds about right.

This summer I made two trips to the island: one with colleagues, the other with family. Together, the two trips totaled 13 days. Half of that time was spent on a mooring in Vineyard Haven Harbor; the other half was spent at a rental a few blocks inland on Skiff Road. Over the course of my family’s week-long stay, four or five different families came and went in the cottage behind the house. A new day would reveal a new car in the driveway and fresh faces swinging on the old, tangled-up swing. Nearby, packs of sun-kissed, salt-licked cyclists pedaled over rolling hills. Roving gangs of wild turkeys fanned out around the island, sometimes waltzing right into the backyard as if they owned the place, much to our hound dog ­Charlie’s delight. At night, we shucked oysters on the porch and scoured the disparate towns for places to eat.

You’re never too old to ride the oldest operating platform carousel in the U.S.

You’re never too old to ride the oldest operating platform carousel in the U.S.

We went to the beach. Sure, Katama Beach has the picturesque views you would normally associate with a popular beach spot, with the occasional biplane overhead (sometimes piloted by a daredevil). But we wanted to throw in a lighthouse too, so we piled into the Jeep and headed to Aquinnah. Driving west, we passed bucolic scenery: green pastures, white fences, long dirt roads; it’s times like this when you can’t help but feel as if you’re driving down the English countryside. Then Menemsha Pond, a tableau of old fish boats lazing slow circles, and finally Gay Head Lighthouse. Once there, the blood-red clay cliffs were reason alone to have come. Post Labor Day but still summer, the crowds were minimal, but it still cost $15 to park. We trooped down to the beach while my mom stayed in the car with Charlie, reading a book. We unfurled our beach towels to lay in the sun—but we didn’t stay long. It was low tide and the sand was packed tight. “It’s like laying on a cement floor,” said my dad.

Situated on a snow emergency route—which became more plausible at night, when the weather dropped to 60 degrees—our rental was in walking distance of the Martha’s Vineyard Museum, which had recently moved from its campus in the old whaling port of Edgartown to a sprawling estate in Vineyard Haven. It was there, almost a month before, where my colleagues and I had bumped into June Manning. We had just purchased coffee from one of the friendly staff. “Make sure you write about how good the coffee was at the museum,” she told us. (It was.)

We ran into Manning on the way out. She’s a tribal genealogist and well-respected member of the Wampanoag community of Aquinnah. She writes a column in the Vineyard Gazette, where she covers the goings-on of the town. “I come from a long line of men from the sea,” said Manning. Today, about 300 Wampanoag live on the island. The Native American influence extends back millenia, with some estimates placing them in Aquinnah as far back as 10,000 years. In Moby Dick, Herman Melville’s character, Tashtego, is a Wampanoag harpooner who hails from Gay Head (renamed Aquinnah in 1997). His unmatched prowess with a harpoon and his well-trained eye for breaching leviathans infers a long line of whalers originating from the westernmost side of the island, as was the case. “There’s a lot of great history here,” said Manning.

As if to underscore her point, she casually mentioned some personal history of her own: While managing the Ocean View Restaurant & Cocktail Lounge in the ’70s, Spielberg was a frequent patron while shooting Jaws. According to Manning, the film director was there almost every afternoon, with anywhere from six to 10 production hands or actors accompanying him. In fact, she and her fiancé saw Spielberg so often they invited him to their wedding.

The Vineyard is a lot of different things to different people. For a young mother, it’s a trip to an alpaca farm with her daughter; it’s a place my friends will always remember tying the knot; it’s a summer playground for the wealthy and where an outboard propeller almost gave me a permanent haircut. With my colleagues in tow, I wanted to show them some of the places from memory. That included Oak Bluffs—tourist central—with its brick-lined walkways, restaurants and bars stacked one on top of another. We even stopped at the late-night confectionery haunt Back Door Donuts and rode the carousel. “This place is like Disney World,” said Editor-in-Chief Dan Harding, not all that joyously.

The nice thing about the island is there is something for everyone: Each of the six towns is unique. “One of the standing local jokes is Martha’s Vineyard is six islands surrounded by water,” said historian Bow Van Riper, who has lived here for most of his adult life. “The towns—despite being cheek by jowl in 100 square miles of sand—are all distinctly different from one another; they all have their own feel and personality.”

We docked the Prestige 460 along the bulkhead of Oak Bluffs Marina, rented a golf cart and puttered around. When that grew tedious, we took an Uber to Bad Martha brewery. In the light, airy tasting room, a mermaid was plastered over all manner of odds and ends, knickknacks, apparel and tap-handles. The image was the same: a black-haired beauty beckoning with one finger like a femme fatale in a smoky room, her visage a lot like a younger Angelina Jolie.

This being Martha’s Vineyard, she even has her own story, a retconned version of the island’s colonial founding. And, no surprise, she comes from the sea, like the island’s pantheon of white whales, curmudgeonly captains and bloodthirsty sharks. Standing in the brewery’s wooden enclosure built by an industrious group of Amish craftsmen in record time, we weren’t very close to the water. But even here, you could feel its pull, its siren song.

The halcyon days couldn’t stay. The boat needed to be returned, and everyone needed to get back to his or her respective lives on the mainland. Raucous sing-alongs aboard the dinghy; breezy afternoons spent in the mooring field, kite surfers weaving between the assembled schooners and motoryachts; the look of envy you would catch in a person’s eye as they walked past the 460 in Oak Bluffs Marina—all of it had to come to an end.

I thought of this on the last night with my family. All day, we had overheard people saying their goodbyes; some of the seasonal workers returning next year, some never to return again. Ferries took away large groups as individuals stood on the gangplank waving to the people back on shore. As the day got longer in shadow and shorter in tooth, a mermaid slithered into my father’s brain. “This house is perfect,” he said. “I’m going to buy it!”

It was a nice thought, but what he really wanted to purchase was our time spent together as a family. Something that could make this feeling last forever. A place to keep the good memories alive; an indelible, enduring place that never fell into disrepair, or required hard inspection or needed serious work. A place that only the Vineyard could produce. Such a thing wasn’t for sale.

This article originally appeared in the December 2019 issue of Power & Motoryacht magazine.