Hiking Cape Ann

One thing you should keep in mind while hiking on Cape Ann is just how much can change over the course of three hundred years. All of my favorite woods walking in my home town of Rockport is located in the center of the cape, a patch of almost 4000 acres of pine, oak, granite boulders, and paths webbed with roots. Miles of trail criss-cross these woods, and while they are well traveled by locals on their walks, it’s still quite easy to set off into the forest and not see another human being until you reemerge an hour or two later. However, these woods were not always this way.

The woods of Dogtown are so named because of the settlement that used to be there; when the English first began to settle in Massachusetts in the seventeenth century, they build their homes nestled on the rocky inland hills of the inside of the cape, safe from hostile European ships and more protected from the local Native Americans. It wasn’t until after the American Revolution that these settlers deemed the coast safe enough to start a life there. Families began to settle the outer coastline of the cape and begin the fishing industry that Gloucester would become famous for. Dogtown (or, as it was known then, the Commons Settlement) became less and less like a prosperous village and more like a footprint — a place of traces where something used to be.

Once Dogtown was totally devoid of human habitation, much of the land was used for grazing pasture by Rockport and Gloucester residents. Vast sections of the densely wooded trails I now know were open, grassy fields, dotted with cows only one hundred years ago.

As I walked with my father, my uncle, Murphy, and my cousin’s dog up a trail off the end of Summit Avenue earlier this week, I thought about these layers of history. Dogtown still feels like a forest with secrets. As a child walking the more accessible, well travelled trails near my parents’ house, I always dreamed that those secrets might involve fairies or elves, something that would be right at home in that moss-covered trunk or that secret dark spring by the side of the trail.

Today, Dogtown still promises secrets, if perhaps less Tolkien-esque ones. The trail that we took this week passes through Briar Swamp — the trail suddenly bursts out of dense trees and into a clearing, where a wooden boardwalk dips and weaves over marshy ground dotted with sheep’s sorrel, Jack-in-the-Pulpit, and curling ferns. It also took us past Whale’s Jaw, a giant granite formation that got its name from its resemblance to a whale’s maw emerging from the earth like the surface of the ocean. Unfortunately, the boulder broke when I was very young, altering the resemblance, but the size of the rocks is still breathtaking.

Elsewhere, you can find the remains of the original Dogtown houses, now just depressions in the leaf matter of the forest floor lined with stacked granite foundations. You can also organize a hike around spotting all of Babson’s “motto rocks.” During the Great Depression, local millionaire Roger Babson sought to put some locals to work and create a meaningful legacy by hiring some stoneworkers to carve inspirational directives into granite boulders throughout the Dogtown forest, phrases like “Kindness,” “Loyalty,” and “Help Mother.” You can find a trail map for Babson’s boulders here.

Even aside from these more unique sites, Dogtown offers beautiful walks. Right now, in mid-June, the woods are bursting with green and quiet streams, and you can find treasures by the side of the trail like beautiful mushrooms and delicate mountain laurel flowers. Murphy ran himself utterly ragged, dashing ahead on the trail and then sprinting back to us, tongue lolling.

Whether you’re a nature lover, a history buff, or a dog walker looking for new places to explore with your pup, check out the maps and guides here for more specific information on how to plan your visit.


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