Dogtown | Gloucester, MA


On Cape Ann in northeastern Massachusetts, between the solid little port city of Gloucester and the absurdly picturesque town of Rockport, there is a high and rocky plateau. Strewn with boulders left behind by retreating ancient glaciers, crossed with old stone walls and little footpaths worn into the flood-prone ground through tangled woods, this inland wilderness is vast (most accounts say 3,600 acres, but this, like everything here, is hard to pin down) and inhospitable.

It was not always like this. In the 17th and 18th centuries, when people left the populated coastal areas to live here, they saw not a desolate hinterland but a mostly deforested expanse of new ground, rocky but full of commercial potential, just waiting for roads and houses and farms. Several hundred people (“80 families,” they are usually called) lived here at the settlement’s zenith. It was known as the Commons or Commons Settlement. A narrative soon developed that its residents had decamped here to shield themselves from pirate attacks and conflicts with Native Americans, though this seems to have been more myth than reality. It is also said that the inland situation of the Commons offered protection from British bombardments and raids during the Revolution and the War of 1812, but the settlement was not inviolable – history records that some American sheep were seized and carted off by the enemy.

In the post-war years, as Gloucester’s livelihood became centered again around the waterfront, most residents of Cape Ann’s highlands trickled back to the coast, and the population of the Commons Settlement dwindled and shifted. Outcasts lived here, and the very poor, and drifters. Witches lived here, everyone said, and prostitutes. Widows lived here, with dogs for protection, the story goes, and although contemporary accounts of the place don’t mention an unusual number of these pets, they are often cited as the reason why the Commons became Dogtown.

If the Commons was respectable, Dogtown was the opposite. I encounter the word “embarrassment” a lot when reading about it, and the word “ghetto.” There were stories of men disappearing there, and tales of supernatural incidents. The once tamed land grew feral again, and though it never stopped attracting a devoted few who loved its wild nature, the place became a byword for inexplicable weirdness and occasional evil. As recently as the 1980s, it was still largely thought of as a mire of drug activity, rowdy parties, and the lurking danger of shadowy men – a fear magnified by several assaults and a gruesome and well-publicized murder. Dogtown is still said to be haunted.

Today, Dogtown is preserved open space, with hiking trails and reservoir views, but something of its ominous old reputation clings to it still. Before I go, I read the warnings: you will get lost; bring extra food and water; this place is confusing; do not go alone. I have done far riskier things than walk by myself through the Massachusetts woods, but I am sufficiently freaked out and I drag a friend with me. We have maps, which turn out to be better than blank sheets of paper but not by much, and a Dogtown app, which proves itself entirely useless when the trail we’re following ends abruptly on a steep hill at an impassable little river. For over two hours, which feel like four hours, we traipse through the woods, scrambling up boulder-littered inclines and crossing streams on narrow planks of wood. We carefully skirt the squishy edges of Dogtown’s old main roads, transformed into mud puddles by recent heavy rains; we soak our sneakers anyway. We try to decipher color-coded trails and the cryptic letters and numbers that mark small remnants of human habitation. When we find one, like the rock on a cramped little hillside that’s carved with D.T. SQ to denote the former location of Dogtown Square, we contemplate how very strange this place must have been, even in its heyday.

The decline of the Commons was quick. Most of the 80 numbered houses, which had stood on named roads, as in any proper little town, were torn down when their owners moved out. The ones that remained were deteriorating. Their inhabitants were former slaves, and healers, and spinsters or widows who lived alone. Among them was a mixed-race woman who dressed in men’s clothing and did men’s labor, and a boy raised as a girl. The people of Dogtown told fortunes, ate Johnny-cakes, and picked blueberries. They often shared houses, swapping addresses as their circumstances changed. When the houses became uninhabitable, they moved into the cellar holes.

By 1830, Dogtown was abandoned. That was the year its last inhabitant, a former slave named Cornelius Finson, a.k.a. Black Neil, was found nearly frozen in his cellar hole and brought to the poorhouse, where he died days later.

For a place so often called mysterious, Dogtown’s past is well-documented, and it has long been a favorite subject of writers, poets, and painters. A good deal is known about who lived in which house, and when, and how many children each man had, and who owned the most sheep. We know that Cellar Hole Number 17 (now, like the others, filled in but marked with a stone) belonged to Dorcas Foster, who was married three times, and that the boggy patch near the Square was called Granny Day’s Swamp.

And yet, as much information as there is, this place still feels unknowable. Standing in the woods, trying to mentally map an old New England town over this jumble of stones, hills, trails, and twisted trees, I find myself questioning everything I know about old New England towns.

I also find myself wanting to categorize this place as it was when it morphed from a village to a folk tale. Was it a wretched slum, home to desperate people? Or a brief utopia free from the constraints of New England society? As my friend and I stand in what our dodgy maps suggest may be Dogtown Common, a flat grassy circle around a lone tree that seems to be awaiting a pagan ceremony, I hope it was the latter. At the very least, I think, it would hardly be the first or the last place to count as both.

There is another layer to Dogtown’s strangeness, imposed on the landscape during the Great Depression. As the nation struggled, Roger W. Babson (the millionaire and eponymous college founder who had predicted of the market crash of 1929) hired unemployed immigrant stonemasons to carve words and phrases into 24 of the plateau’s massive boulders. These now make up a quasi-trail of judgy public art, confronting hikers with a combination of motivational tips, moral precepts, and vaguely inspirational nouns. We stumble on Truth, Courage, Loyalty, Kindness, Intelligence, Integrity, Initiative, Study, Be On Time, Keep Out of Debt, Spiritual Power, Industry, Ideas, Kindness, and Work. We do not find If Work Stops Values Decay, Help Mother, Be Clean, Be True, Use Your Head, Prosperity Follows Service, Never Try Never Win, Save, or Get a Job.

The boulders, removed from their 1930s context, resemble a pretentious, outdoorsy treasure hunt. (If they were in the Hudson Valley, they’d be sandwiched between lunch and dinner at twee restaurants in an itinerary in New York Magazine, and it would cost $20 per person to see them.) But their advice, offered kindly but so blithely, also uncomfortably recalls today’s debates about what to do when prosperity can no longer be a given, and whether initiative is enough anymore, and who is entitled to what. Do people who manage to keep out of debt, or who boast of their spiritual power, deserve something the rest of us don’t? Whose ideas count as Ideas? Exactly which values decay when work stops, anyway?

In the woods, my friend and I are never truly lost in the helpless, panicked, burning daylight sense. But we frequently find ourselves unsure of how to get from where we are to where we know we should be, or perplexed at how we arrived where we are. The trails and locations on the map don’t seem to match the distances and directions of the terrain, and we wander far enough from our starting point that the loud booms echoing from the nearby shooting range are not alarming but comforting, proof of normal human life continuing outside of Dogtown’s gates. We get just as lost as one should get in Dogtown, I suppose, just lost enough to take courage from the Courage boulder and to contemplate the attitudes of witches.

We finally emerge once again at the parking area and drive back to downtown Gloucester, abandoning the eerie inland rock formations as the early settlers of the Commons did. But we are just cold and hungry and bedraggled enough to bring a bit of Dogtown’s wild essence with us.

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