Twelve miles out to sea from either Port Clyde or Boothbay Harbor in the lobster fisher’s paradise and artist colony of Monhegan Island, cast away from almost everything, even the houses have big personalities. They hold stories of generations, some that are still being written.

Up a dusty narrow road, a bright blue door pops out from an old white cottage, the only house around, and upon walking up I realize I’m entering a gallery once owned by Thomas Edison’s son Theodore and his wife Ann, a painter. From low on a studio shelf, tucked away from the mosaics and the stately sculptures cast in bronze, I pick up a tiny, well-loved flip book with curling corners and rough illustrations of playful little goats. It’s a family relic brought over from Monhegan’s mostly uninhabited little sister, Manana Island, where the owner of Edison Studio, artist Daphne Pulsifer, has lived for decades with her husband, Danny Bates, in what’s got to be the most peculiar and fascinating house of them all.

Its dizzying octagonal roof is an enigma to newcomers waiting for the ferry workers to tie up to the dock. Tourists have wondered about this whimsical house at the center of Danny Bates’s herd of goats, which are not only illustrated in the book but still grazing Manana’s rugged green hills and steep rocky outcroppings. Practically every year, Monhegan’s 59 year-round residents and the summer swell have watched Danny paddling back and forth in the harbor, hammering away, and adding new angles to the home.

Only two families are known to have lived on Manana, and the fairytale story of its oddball house begins with a hermit, Ray Phillips, whose obituary landed on the front page of the New York Times in 1975. Phillips had built Manana’s first home, the original driftwood shack, and as hermit life goes, he mostly kept to himself until eventually islanders watched the kerosene lantern burn out in his window. With the hermit gone and his shack beyond repair, his friend Danny began building a house near the same spot, raising one round of kids there, and then another after he married Pulsifer. To me and anyone who’s been to Monhegan’s Fish Beach or Lighthouse Hill, Danny’s goats and some sheep look like specks of dust; to this family they’re practically pets.

The same day when I walk into the Edison studio, I also meet one of the kids who grew up in the house: Danny’s son— Pulsifer’s stepson—Orca Bates Melenbacker, now 46. Orca is on his annual visit to the island from his home in Pine Island, New York, and he and I strike up a conversation about life on Monhegan 30 years ago.

If the name Orca Bates sounds familiar, maybe you’ve seen his portrait hanging in museums and national galleries. Orca Bates was once the favorite child subject of Jamie Wyeth, Maine’s most famous living artist, who still summers on Monhegan.

Orca points to the spot on the dirt road by the woods where Wyeth first approached him in 1988 about posing for a painting. He was 13 at the time. Orca agreed, and the next day he went to Wyeth’s house on Lobster Cove, where he asked Orca to put on a paint-splotched Hard Rock Cafe T-shirt (a gift to Wyeth from Arnold Schwarzenegger) and handed him a taxidermy seagull. Wyeth stayed through the winter just to finish that first oil painting of Orca, which he had him sign a year later when it was complete. Portrait of Orca Bates, a work in contemporary realist style depicting an island boy clutching a seagull, hangs in the Farnsworth Art Museum in Rockland.

“Everything on the island belongs to someone, unofficially—even the seagulls.” I remember my neighbor telling me this when I stayed on Monhegan a few years ago. A seagull had turned up outside the door of my rental house with a broken wing. I understood what she meant—that the people of Monhegan consider themselves stewards of their beautiful rolling land ending at the tallest cliffs on the East Coast. It filled the canvases of Jamie Wyeth’s famous father, Andrew Wyeth, a watercolor painter; his grandfather, the illustrator N.C. Wyeth; and every artist from George Barrows to Edward Hopper. Theodore Edison took the responsibility seriously in 1954 when he bought 350 undeveloped acres to form the first land trust in Maine. But seagulls will do what they want, and it was the freedom of Monhegan’s seagulls that inspired Wyeth to approach Orca in the first place. He called him “more of a seagull than a person.”

“My friends and I were terrifyingly unsupervised growing up on Monhegan, climbing cliffs on the backside of the island,” says Orca. As a teen, he was always getting into trouble. Back then the island was a different place with fewer rules.

“You just sort of knew everybody. My dad and mom knew Jamie— that whole generation grew up together. They went to the same parties,” says Orca, whose great-grandmother had started summering on Monhegan, followed by his grandmother and an aunt. Danny Bates and his stepmom were the first of the family to live there year-round. “It was a wild place back then,” says Orca. In many ways, it still is: there’s still no real law enforcement or healthcare.

With limited electricity and only a boat or two a day going out in winter (if you’re lucky) there wasn’t much for a kid like Orca to do but haul traps from a skiff—Monhegan is the only spot in New England that requires year-round residency to qualify for a lobster license—run around Manana with the goats, and party with the island kids in a shack next to the pizza joint.

When the summer islanders went home and Orca was left with the few remaining kids in a one-room schoolhouse, he was happy to sit for Wyeth, sometimes for four or more hours a day. Wyeth paid well—better than mowing lawns—and the days turned into months, then years. As he grew up, he became the subject of many paintings, and Wyeth’s muse and friend. The two would talk for hours, taking breaks to fire guns off the porch into the Atlantic—“right over there,” Orca points to Wyeth’s “Kent House,” depicted in the 1971 painting. The gray shingled cottage was built on the southern tip of the island in 1906 by the landscape painter Rockwell Kent for his mother. Wyeth purchased it in 1967 at age 21 with the money from his first public exhibition, and there he began to paint what he called “the less-celebrated aspects of island life.”

Next to me on a rocky hill, gazing out at the waves from under swooping gulls, Orca went back in time. “I spent a lot of hours with Jamie over those years. I remember there wasn’t much of a break between paintings, maybe a month or two, and then he’d have another idea with a bunch of props, like his whale jaw still hanging on his living room wall,” he says.

When school started back up, Orca took the seaside path every day to the home of his new artist friend, where he got to watch screenings of prereleased action films on VHS, like Cobra starring Sylvester Stallone, and Red Scorpion. “Jamie had this wall of tapes sent from the directors that were worth like hundreds of dollars apiece,” says Orca. His weathered off-in-the-distance gaze disappears behind a boyish smile, and I see Wyeth’s fascination. Quiet. Reserved. Raw, and rough by now. Hard to reach, but you feel like you’ve won the lottery when you finally get him talking. You see his depth. “That water is no joke. It’s beautiful. It’s powerful. It’s cool looking. And it will kill you,” says Orca, who lost a friend off the cliffs.

Five years later, the painter had finished four works with Orca’s name in the title, his signature on each painting, and numerous others in the permanent and temporary collections of the Boston Museum of Fine Arts, Crystal Bridges Museum of American Art, the Delaware Museum of Art, Seattle’s Frye Art Museum, and others. When Orca attended high school off the island at Gould Academy, Wyeth flew his helicopter in to hand Orca his finished portrait and hosted an art show for him and his classmates. And they still meet up on the island to catch up when Orca is in town.

“Jamie and I were always buddies. He’s definitely eccentric. He speaks his mind, no apologies, and is very to the point. He’s just a good guy to hang around,” says Orca, who was used to tripping over artists at their easels and inside their studios, starting with his mother, then Pulsifer, and later his sister and younger brother Cat, a Maine jeweler who also modeled for Wyeth once or twice (in “Cat Bates of Monhegan,” 1995). It should be no surprise, then, that Orca’s wife is an artist, too.

For many years Orca, who now owns a shipping container company called Box4Grow, hated coming back to the island: it felt small and “everyone was in your business.” But eventually, he came back to the goats and to the only home on Manana, and to conversations with his old friend, Jamie Wyeth, inside his cottage by the sea.

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