Off Beat
“You can’t really step off the trail if you’re hiking Mount Katahdin and have some really good empanadas.”
Millers River in Cambridge, part of the new Boston Boundless Trail. Miles Howard and Walking City Trails
June 5, 2026 | 9:16 AM
3 minutes to read
Playing jump rope with city limits and criss-crossing Boston’s borders to sniff out unusual scenery, a new 91-mile urban hiking trail promises an epic adventure for wanderers, Strava fiends, and nature lovers alike.
The “Boston Boundless Trail” officially launches Saturday, laying out an ambitious loop that loosely traces Boston’s perimeter while passing through each adjacent city or town. Split into 12 sections and coming in at a whopping 90.9 miles, the trail begins in Boston’s North End and finishes in East Boston, with an optional ferry ride across the harbor to go out on a high note.
The brainchild of Walking City Trails, Boston Boundless doesn’t actually create any new infrastructure, according to Miles Howard, a freelance journalist and the group’s director. Instead, the trail curates existing paths that will guide walkers across iconic bridges, through hidden greenways, and past architectural oddities and sandy beaches.
“Brevity is not really the key right here,” Howard joked. “A walk can be somewhat casual and aimless, and a hike, you have a little bit more intentionality behind it, and you’re also committing to being outside for a considerable amount of time in the elements. And that holds true for a city, a backcountry area, you name it.”
Walking City Trails launched in 2022 with its namesake 27-mile trail, which connects some of Boston’s most scenic green spaces. The 31-mile, elevation-minded “City On The Hills” trail was a more recent addition, ushering visitors to some of the highest points in the city.
“The idea there, which really grew into the foundational mission of the project, was to illuminate not just how many denominations of green space there are in the city of Boston that make for fantastic walking, but how a lot of these spaces and the neighborhoods in which they’re rooted are actually a lot closer than we might realize sometimes, and that walking can be a way of realizing that,” Howard explained.
He said the broader mission of Walking City Trails is “social cross-pollination,” or encouraging people to explore beyond their own neighborhoods.
“Boston is a historically segregated city, where people often have perceptions of communities and places as being far apart and disparate from each other,” Howard noted. “And in fact, it is entirely possible to walk from south to north across the city in the better part of a weekend — or even for some people a single day — and see so much of what this cityscape is made of.”
When Howard faithfully trekked Boston’s squiggly perimeter in 2024 — an exercise he documented in a Boston Globe opinion piece — he said the experience “kind of illustrated to me how arbitrary these borders often feel.” He’d long toyed with the idea of a Boston perimeter project for Walking City Trails, but a lingering affordability crisis instilled in him a new sense of urgency.
“I’m a working writer, which does not bode well for my opportunity to afford staying here for a long time,” Howard acknowledged. “As much as I enjoy being rooted here and want to make the most of it, I started thinking last year about, like, ‘What would I regret not trying to instigate [with Walking City Trails] if I had to move from Boston in a year or two?’”
He was particularly drawn to the idea of a trail that reimagines Boston’s border.
“Thinking about the history of the Boston region, the level of inequality in this area and historic segregation, I think that the idea of reinterrogating what those lines are — maybe even letting go of the idea of lines of demarcation — I just found that more and more intriguing, thinking about this idea,” Howard added.
Cutler Park Reservation in Dedham, part of the new Boston Boundless Trail. – Miles Howard and Walking City Trails
To that end, the free-to-use Boston Boundless Trail will make its debut on the Walking City Trails website Saturday for National Trails Day. Howard said he’s also working on a list of places to stay overnight along the way, though he expects most people will enjoy the Boston Boundless Trail in segments and make use of its ample public transit stops.
Comfortable shoes, sunblock, water, and rain gear all come highly recommended, but Howard noted the trail also offers plenty of opportunities to refuel and stock up along the way.
“You can’t really step off the trail if you’re hiking Mount Katahdin and have some really good empanadas,” he said with a chuckle. “And I think that that’s something that when you have the opportunity to do that on an urban hike, it’s worth savoring.”
Abby Patkin is a general assignment news reporter whose work touches on public transit, crime, health, and everything in between.
Sign up for the Today newsletter
Get everything you need to know to start your day, delivered right to your inbox every morning.
