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Dogtown in Cape Ann, MA | Abandoned Settlement Mystery

With an eye out for cellars and rock walls and signs of Finson or other ghosts, I continued to walk in Dogtown, and I kept getting lost. My father, who had taught my sister and me how to navigate the woods behind our house when we were growing up, took exception to this. Slow down, he said. Retrace your steps the moment you’re not sure where you are. I knew to carry a compass and to watch the sun on my way in, but in Dogtown, it seemed, the sun reoriented itself at will.


On Cape Ann, what did or might have happened in Dogtown has long been part of local lore. “The walled ruins of Dogtown draw the curious and speculator,” wrote historian Charles Mann in 1896. “Why did more than one hundred families exile themselves from the life of the villages so near them, and dwell in loneliness and often in poverty, in this barren and secluded spot?”

That same question was at the heart of a Sunday morning walk taken recently by a local family to celebrate the birthday of its matriarch. In addition to Barbara Stewart, who was turning 80, three of her daughters, two sons-in-law, and four grandchildren gathered in a parking lot off Cherry Street in Gloucester. Directing the two-hour tour were Seania McCarthy and Dee McManus, who offer guided hikes in Dogtown. Sunlight filtered through the trees; McManus’s dog, Cooper, led the way.

“I’m so glad we’re finally doing this,” said Stewart, beginning the easy ascent on a paved road that soon gave way to gravel. A few minutes down Dogtown Road, McCarthy directed the family to pause, indicating a heap of rocks in the woods — an ancient house site. “Number 15; this one belonged to Easter Carter,” she said. McCarthy described Carter’s two-story house, grand by Dogtown standards, and Carter herself as a spinster who nursed others. She also alluded to an upstairs tenant: a cross-dressing stonemason, a former slave named Old Ruth, a.k.a. John Woodman.

“It’s all interesting,” said Stewart, leaning on her walking stick to listen to the story of Carter’s life and–at cellar hole #17–that of her neighbor, Dorcas Foster, who allegedly arrived in Dogtown as a young girl after her father was killed in the Revolutionary War.

After about 30 minutes, the group arrived in Dogtown Square, a humble place even as ancient squares go. The cellar hole from Granny Day’s schoolhouse and a sheep-swallowing swamp lay to the west, Wharf Road to the north. McManus and McCarthy led everyone south, into the terminal moraine that is Dogtown’s most prominent topographical feature. This area is a product of the Ice Age, when melting glaciers dropped their rocks, some as large as houses, plus other “erratics” borne from far away.

Roger Babson eventually donated his Dogtown land to the city of Gloucester, whose Dogtown Advisory Committee purchased additional properties and organized efforts to maintain the area.
Photo/Art by Sara Gray
Roger Babson eventually donated his Dogtown land to the city of Gloucester, whose Dogtown Advisory Committee purchased additional properties and organized efforts to maintain the area.

It’s also the site of the Babson Boulder Trail, named for financier Roger Babson. A Gloucester native who founded three colleges, Babson purchased much of Dogtown’s land and turned the place into something of a classroom by commissioning quarry workers to carve inspirational phrases into 24 of the most imposing boulders here. Of all the efforts to develop Dogtown — including a 1944 plan for an airport in the Whale’s Jaw area, a 1967 Department of Defense consideration of Briar Swamp as a radar installation site, a 1970s proposal for an Old Sturbridge Village-style attraction, and, most recently, an attempt to locate a windmill farm here — Babson’s plan was the only one to materialize.

Babson’s 1930s project didn’t meet with universal approval, though. Reading from a notebook, McCarthy quoted Babson: “My family says that I am defacing the boulders and disgracing the family with these inscriptions, but the work gives me a lot of satisfaction, fresh air, exercise, and sunshine. I am really trying to write a simple book with words carved in stone instead of printed paper.”

McCarthy pointed out several of the inscribed boulders, many of which were not immediately visible in the dense woods: Be on Time, Study, Initiative, Keep Out of Debt. “Definitely New England values,” said one of Stewart’s sons-in-law. “Puritan,” said another.

Two of the Stewart grandchildren posed for a photograph beside Use Your Head, and — after a non-Puritan-like pause for chocolate-chip cookies and snake viewing at Spiritual Power — the whole group assembled for a picture in front of Kindness.

It was nearly noon, time to turn back. On the way, McCarthy pointed out the place where James Merry, a fisherman and railroad worker also known as “the Dogtown matador,” died after being gored by a bull. Three rocks here bore carvings: the first, Jas. Merry Died Sept. 18 1892; the second, First Attacked; the third, a Babson inscription, Never Try Never Win. “Maybe he was referring to the bull,” someone said.

Turning back onto the trail, Barbara Stewart headed in the wrong direction. “This way, Mom,” said one of her daughters. Stewart swung around: “I’ll bet it’s easy to get turned around in here.” McManus said that it was, that it was easier to find your way in late fall and winter, when the leaves were down. She mentioned, too, that it was beautiful. Stewart paused, took in a sun-dappled boulder to the left and an unexplored path to the right. “We should come back,” she said.

I understood what she meant. My own hikes in Dogtown continued through a summer and fall, on Halloween and during hunting season, when I saw hunters but no deer. In the spring, perennials bloomed. I grew to love the place — I found it finite and increasingly navigable. There was also disappointment. I went in search of Whale’s Jaw to find it broken in half; succeeded in locating only 20 cellar holes, when 40 were listed. Even so, through good walks and bad, I felt connected to the place. In mapping its terrain, I figured out some things about myself.

Please Note: This information was accurate at the time of publication. When planning a trip, please confirm details by directly contacting any company or establishment you intend to visit.

Updated Friday, October 24th, 2008

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One Response to Dogtown in Cape Ann, MA | Abandoned Settlement Mystery

  1. Sandra October 9, 2014 at 6:33 pm #

    Since I am an artist, I was a fan of Marsden Hartley’s art. I enjoyed this article very much. Thank you.

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