Dogtown: Creepiest Haunted Site In Massachusetts

When you think about eastern Massachusetts, most people instantly think about cities and towns like Boston, the historic Lexington/Concord area, Walden pond, industrial Lowell, and when imagining the areas of land by the ocean, there is Plymouth all the way down to Woods Hole, around to the Cape and then off to the islands.

North of Boston and around Boston harbor you pass Nahant, Salem, Marblehead, and on around up into Cape Ann. Gloucester is the enormous gateway before driving into the much smaller Rockport. On the north side of Cape Ann, shared by both communities is roughly 3000 acres of wildnerness and exotic geological formations that take the breath away.

There are numerous quarries to carefully walk up to, bike paths both flat and challenging, paths defined on both map and earth to amble about, and the less traveled paths that can lead to private discoveries. Depending on the season and even the time of day, magic awaits the avid photographer, bird watcher, and amateur geologist.

The history of Dogtown dates back to 1693 and though the ground is definitely not suited to agriculture the area was settled because of the protection it offered the townspeople from pirates and enemy natives.

Dogtown in 1908

In the middle 1750’s a new coastal road opened and people moved away into Sandy Bay (now Rockport) and the Annisquam and Lanesville areas of Gloucester abandoning the homes they had built there. The population dwindled down to the widows of sea-goers and soldiers who died and never returned.

They were too poor to move and were afraid so they kept dogs for protection and companionship. As the widows died themselves, the dogs were left behind and became feral. It became a ghost town, some say literally.

Ghost stories and legends about of one of the last remaining residents’ of Dogtown being a witch. Depending upon who tells it, Peg Wesson lived in Dogtown or just over in Gloucester proper. One legend states that a couple of boys had angered her and she had cursed them.

They left for jobs in upper New York state to earn money for their families and Peg would not let go of her anger. She went into her front yard, shot two arrows into the air that never landed, not in Dogtown.

The families of the two boys received word that they had been killed when two arrows fell out of the New York sky and straight through their hearts. Never proven, differs upon who tells it, but it’s an odd tale that lingers around Dogtown.

There are stories of begger women asking for money at the entrance to some of the paths and curse the ones who carelessly pass them by. Dogs barking can be heard but most people attribute it to hikers.

The folks who live on the edges of Dogtown wonder why those hikers are out there after midnight and if their dogs are on leashes because of all the hidden basements and quarries that dot the area. And on a weirder note, Dogtown is one of the few places that has rumored werewolf activity.

It’s an area that is rife with superstition, ghost stories, and great beauty. Walking through Dogtown requires attention be paid to the chosen path for reasons based in reality.Exposed tree roots, sudden drop offs, the slick rocks that slide down into the water that’s collected in the quarries, and, when you get into the center of Dogtown, the exposed basements that can be hidden behind shrubs and trees. It’s a historic and beautifully rough place.

If you get the chance to go, plan a walk of several miles past the Babson stones carved with sage words of advice. Take water, a snack, and a cell phone because you never know if one of those barking dogs isn’t really a barking dog.