In Massachusetts, walking around town used to be something that officials in every municipality were legally obligated to do. “The earliest version of the law that I could find was from 1651 — an Act Respecting Bounds of Town Lands,” explains Jake Sconyers, host of the HUB History podcast, which explored the civic tradition of “perambulation” in a 2017 episode. Officials from neighboring towns would get together and walk their border every five years, making sure that the stone markers that denoted town lines hadn’t been moved. (You can find such markers in Stony Brook Reservation dating back to the 19th century, before Boston annexed Hyde Park.)
According to Sconyers, this tradition may have been borrowed from English church parishes. “The Puritans who settled Massachusetts Bay were contractual people,” Sconyers says. “The charter that secured their liberty was a contract with the Crown. The covenant that guaranteed their salvation was a contract with God. So the idea that there would be deeds referencing these borders which would be entered into a legal record fits within Puritans’ contractual framework of the world.”
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As surveying technology evolved, town officials in Massachusetts stopped perambulating their bounds. But there’s still a law on our books compelling local officials to undertake a circular walk around town every five years and inspect the boundary markers. It’s the legal equivalent of a forgotten bag of moldy carrots at the back of the crisper: outdated and kind of funky.
And when I learned about the old law, I wondered, What if I perambulated Boston today? What would that be like?
Walking in a giant “circle” around a city is becoming one of the great urban adventures of our time. In New York, people hike the 32-mile shoreline of Manhattan Island in an event called The Great Saunter. In Berlin and London, the 66 Lakes Trail and the Capital Ring Walk allow you to orbit the respective cities by foot — through woods, wetlands, and suburban villages. And on a recent visit to Philly — a few months before my perambulation — I participated in the Walk Around Philadelphia, a twice-a-year pilgrimage around the city’s perimeter led by local artist and community organizer J.J. Tiziou. Perambulating Boston’s bounds in 2024 struck me less like a chore and more like the kind of gonzo journey that you can either thrill or alienate people with at work mixers. Plus, it was local. Instead of springing for a trip to Spain’s Camino de Santiago or any one of the other long-distance walks that are in vogue now, I could take a pilgrimage at home!
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A hike through Logan
Turning to the AllTrails app — basically the Google Maps for walkable trails and spaces — I spent several days plotting my route. Since our city’s perimeter passes through lots of private properties, the park paths and sidewalks that I took would have to be a rough approximation of the border. In places, I would need to decide between dipping slightly out of Boston or back in, and I would choose the way that yielded the more interesting scenery.
Like a thru-hiker planning to take on Vermont’s Long Trail, I divided my Boston hike into segments. And after selecting a quiet week in mid-April for attempting the hike, I took to my social media accounts and invited people to join me for as much or as little of the Boston walkabout as they felt like.
I received encouraging words (“Good luck on your journey!”), tips about potential trespass zones (“There’s a gate that can easily be jumped”), and an offer to refill my water bottle at a house by Olmsted Park. But I didn’t expect anyone to come out and follow me down this strange path.
Katie was the first person to prove me wrong. From the Harvest River Bridge, we spent the first hour ambling past rapids and cascades on the Neponset River through a corridor of deciduous trees. As the canopy gave way to marshy cordgrass, we reached Dorchester’s Tenean Beach. Steps from here, Phillips Chocolates, a decades-old sweets emporium, provided sustenance in what was otherwise a wasteland of car dealerships and aggressive traffic. Castle Island was our destination for the day, but it was a smaller and lesser-known island that really lingered in our memories over dinner that evening: Victory Road Park, a tiny wooded oasis connected to the Dorchester coast by a footbridge, in the shadow of I-93. Someone had tied plastic crates to the trees, to be used as makeshift receptacles for bags of dog poop. And evidently, someone emptied them. But who?
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The beauty of urban green space hinges on unseen volunteerism. When Katie and I caught the MBTA ferry from Long Wharf to East Boston the next morning — to walk a loop around the Eastie perimeter — we came to appreciate these acts of service even more. After following the Boston Harborwalk from Lewis Mall to Massport Harborwalk Park, we hiked through Logan Airport: ground zero for the historic emission pollution that has likely exacerbated health problems among Eastie residents.
We blended right in with the legions of jetlagged travelers, clutching our backpack straps and sauntering between the terminals through pedestrian passageways (one of which contained the entrance to Logan Airport’s chapel, where a laid-over traveler was snoring in one of the pews). And yet, within an hour of leaving the exhaust of Logan behind, we were standing on an observation deck inside the reedy depths of Belle Isle Marsh Reservation, watching planes land and gazing across the water at downtown Boston.
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And we weren’t alone. Two other perambulators had temporarily joined us.
Dawn Peterson had driven over from Acton for her son Seb’s soccer game, and she had seen my open-invitation posts about hiking the Boston perimeter. “I just thought it would be fun, and I think it’s great that you’re doing this walk,” Dawn said as she and Seb walked with Katie and me on the wandering pathways through the marsh. It was a brief rendezvous — Katie and I had to reach the crumbling Suffolk Downs site before looping back toward the harbor waterfront, and it was clearly time for Dawn and Seb to split for a post-soccer lunch. But I was pleasantly surprised by what had just happened. My social media posts about the perambulation had blown up, suggesting a deep and collective curiosity about what lies on the bounds of Boston. Dawn and Seb had gone out of their way to poke around with me for barely half an hour. The curiosity was escalating.
A cow, a turkey, and a potato memorial
After a day of stretching and refueling with Thai noodles and imperial IPAs, I returned to the core of Boston and ambled through the fish-packing plants of the Seaport and the paths on Fort Point Channel before following the Harborwalk across the Charles to the U.S.S. Constitution. It was a solo chapter of my perambulation.
But the next morning, my dad joined me for the grittiest stretch of the hike yet — a sawtooth-shaped passage through the industrialized territory on the Mystic River. Beneath I-93, we found the Potato Shed Memorial — a stone sculpture of potato sacks, which were once kept in warehouses along the estuary that’s now hidden under the highway. Would either of us return here to admire the potato sculpture? Would we bring friends? I thought about this as I recrossed the Charles on the locks path to reach Esplanade Park. Landmark parks inspire repeat visits. Why not urban oddities as well?
The greatest oddity of my Boston perambulation, however, was always going to be Brookline. Given the town’s resistance to annexation by the City of Boston in the 1870s — a means of preserving its suburbanized landscape — walking the Brookline-Boston border to get to the Newton-Boston border made the perambulation 10 miles longer than it would have been if I had treated Brookline as part of Boston. I followed the Charles River inland before looping back toward Boston via Chestnut Hill Reservoir and Corey Hill. This suburban slog featured numerous signs denoting the Brookline border.
When you stand by one of these signs and look around, the differences between Brookline and Boston feel arbitrary. Then you remember that Boston’s population — and housing supply — have grown far more than Brookline’s in recent decades. At a time when housing prices are causing a regional crisis, such deliberately paltry growth can feel like putting up walls to keep people out.
Walking can be a balm for this atmosphere of exclusion that you can feel on the tonier edges of Boston. After another rest day, I was accompanied by Somerville residents Austin Paul and Phoebe House — both training for the NYC Great Saunter! — for the leafy 13-mile trek from the BU Bridge to the Dedham Mall.
We marveled at the goslings on Jamaica Pond and a long-horned Scottish highland cow in Allandale Farm, and we ran from an aggressive turkey in a patch of West Roxbury woods owned by the Dana-Farber Cancer Institute (that we might have been trespassing through). We didn’t see many other walkers as we snaked between multimillion-dollar houses. But there were public sidewalks and paths to wander. We were here because we could be.
Still, cheeky as our passage through wealthier neighborhoods often felt, the animating desire of this adventure was curiosity — wondering what’s out there on the fringes of this, or any, major city. As I closed the “circle” on my final walk, from the Dedham Mall through a dense maze of West Roxbury and Hyde Park streets, back to Mattapan and the Neponset River, I linked up with two more social media onlookers who decided to get in on the action: Tori Dutcher-Brown (on her day off from bartending in the Back Bay) and Chelsea Jimmis (visiting Boston from Providence). “I was surprised by how big the Boston city limits are,” Dutcher-Brown said as we pushed through thick, snarled woods along Mother Brook. “And I love walking around the city. When I go to a new restaurant or run an errand, sometimes I’ll walk there and see what I find along the way.”
Five minutes later, we emerged from the woods beside a roaring dam waterfall, absent from the maps that I had studied. We still had 7 sun-baked miles to go before I could step onto the Harvest River Bridge again and toast the end of the adventure with a tallboy from a liquor store. But this shared moment, in this place, spoke to the possibilities of a walk around town. Perhaps the old perambulators were onto something more nourishing than taking municipal measurements, when walking the border was tradition. There’s rustling beauty, mesmerizing eyesores, and things that defy explanation on the edge of town.
Miles Howard is a freelance writer in Boston and the founder of the Walking City Trail. He publishes the weekly hiking newsletter Mind the Moss.
