Central to this surprise accolade was the 27-mile Walking City Trail (WCT), connecting seventeen neighbourhoods from the Neponset River Reservation to Bunker Hill Monument. 

Miles Howard spearheaded the project. “I sort of fell out of my chair when I read that,” he recalls. “I chuckled at the idea of the Outside audience reading through this article and then getting this category and going, ‘Boston? What the fuck!’”

Miles was already pondering the possibility of bringing backcountry-style hiking into urban spaces when he walked San Francisco’s 17-mile Crosstown Trail, which dissects the city from the northwest to southeast. Though initiated by the city council, it was completed by a coalition of volunteers impatient with persistent delays, complete with written directions and free maps. Inspired by his experience, and the trail’s roots, Miles returned to Boston and began plotting.

But how to begin?

Urban trail development is logistically simpler than backcountry trail building in that the building is already done; the task is simply to curate and promote. But proposing a trail through a landscape dense with millions of potential stakeholders poses other challenges. Would it not be presumptuous to single-handedly curate a route that, intentionally or not, may seem like a definitive tour?

The first challenge was therefore to decide between recruiting collaborators and proceeding collectively or forging ahead with a prototype before inviting feedback and input. “In my experience, the difficulty you run into with the former approach, while more holistic in the long run, and reflecting a community vision, is that nothing happens for a long time,” Miles says. “I wanted to act on this idea while the energy and excitement were still very fresh.”  

With some reservations, Miles began plotting a path connecting Boston’s abundant green spaces. Many days of GPS investigation and on-the-ground corroboration later (he plans to publish an urban trail-building guide to the WCT website in late 2023), he published the first maps and started offering guided test hikes in June 2022. These soon reached capacity, and led to connections and suggestions that have improved the trail. Miles now works with a team of trail developers – including Matthew Broude, Jules Murdza, and Patrick Maguire – and wider stakeholders, including supportive councillor Kendra Lara.

The approach seems to have paid off. Though Miles expected pushback against his initial decision to act alone, he thinks his openness to support and suggestions, as well as the novelty of the project, have kept this to a minimum. The most notable opposition, he says, has taken the predictable form of NIMBYism – specifically the removal of trail signage. 

Miles has also made it very clear that his aim is not to establish the One True Boston Trail, in a city which already enjoys the seven-mile Emerald Necklace and plenty of trail-threaded green spaces. Rather, he hopes to “gin up enough community interest in urban trails in general that more trails can take root in the city of Boston in the future. Possibly more trails like this, designed by community organisations first and foremost. Possibly even trails that are shepherded by the city in some way.”

For Miles, the WCT goes beyond Boston. He wants to help forge a path into a collective reimagination of cities. “What I would love to see a couple of decades from now,” he explains, “is deeper and wider recognition of the urban environment as a place for exploration, discovery, and fun. So much of the way in which we’ve thought about cities historically has been: these are places of commerce, first and foremost.”

This is not just imaginatively limited, he thinks, but “a very historically short-sighted view of how cities have been perceived at various times, especially when you consider what happened in the wake of the Civil War in the United States, with the development of public parks in places like New York and Boston, and how that radically changed our concept of what you could experience in a city.” 

In recent years, discontent with the forty-year neoliberal consensus has reached a rolling boil in both the US and the UK. This consensus leaves nothing untouched, including the use of urban space. Deepening inequalities, hollowed high streets, and housing crises have been the story so far: rich supplanting poor, luxury investments supplanting community amenities, private space supplanting public provisions.

It’s a bleak picture, and urban trails won’t solve it alone. But they might seed some of the green shoots required if we are to grow a new way of thinking. In the UK, projects like London National Park City, a grassroots blueprint for making London greener, and Slow Ways, which is crowdsourcing walking paths between urban hubs, offer hope. In a US context, Miles cites St. Louis, “ a much more historically car-reliant city than Boston.” The city is in the process of transforming many of its old roads and industrial corridors into “a connective walkable and bikeable greenway system that one day will be able to give you access to most of the city's neighbourhoods. I tried walking a few of those greenways … and it was incredible. It was like going through a primeval forest in the middle of this Midwestern city.”

Covid shone a harsh light on the impact of green spaces on physical and mental health, and the inequalities resulting from current allocations. Miles thinks this has fostered more appreciation for our backyards, for setting out into and beyond the familiar, and for reimagining urban nature connection.

Unequal access to green space is one of Miles’ core arguments for urban trails. “In any city you want people to have a collective ownership and stewardship of green spaces,” he says. “In a place like Boston – where there are such glaring inequities in our economy, and there's a long history of segregation – that's really difficult to pull off for people beyond their local lens.”

“In an ideal city, somebody living in any neighbourhood would have as much of a sense of ownership of the park that's down their block as a forest that's maybe three neighbourhoods over,” he continues. “Especially because parks in Boston and many other cities are not equally kept up and funded … I think it's important to make people feel that this entire ecosystem of green space is theirs.” 

Not that this excuses under-funding poorer neighbourhoods. “On the flip side, because wealthier neighbourhoods do tend to be more atmospherically and structurally exclusive, I think it's really important for somebody who lives in a neighbourhood that is more historically marginalised and under-privileged to be able to feel that they have every right to go to their local park as much as they do to visit some immaculately upkept homesteadian wonderland in a ritzier part of Boston. That's a bit idealistic, but at the same time green space is one of the few common goods that we have at this point, and it scares me to think about it becoming perceivably more privatised as inequities worsen in cities going forward.”

Better connecting neighbourhoods can also help correct perceptions of so-called ‘dangerous neighbourhoods’, something Miles has received some concerns about. But he sees this as an opportunity, not a threat. “A lot of the areas that we perceive as historically being unsafe in cities are actually quite vibrant communities,” he says. Like many neighbourhoods, they may be “prone to occasional violence and such, but at the same time they have many overlooked aspects – not just their green spaces, but in small business offerings, local art, and more. One of the ways in which we demystify the idea of ‘bad neighbourhoods’ is by actually encouraging more people to walk through.” 

Combining connected segments into a continuous trail tells and names a story, a history, a thread of argument. It makes a statement about the possibility of moving anew, of living a little differently in this place. Urban trails encourage a more interconnected lens on green space and social life.

Reimagining a backcountry ethos for urban environments is an important part of turning these possibilities into realities. Charting a route, offering maps, erecting signs and borrowing the language of ‘hiking’ can all help walkers “engage with the city as though they were going on a big exciting expedition that they have fun planning for,” says Miles. He’s heard from people who have travelled from afar to walk the trail, and a local couple who thru-hiked it over two days, treating it as a trip away. 

Following this thread is a fun thought experiment. After our conversation, I envision groups of friends structuring their visit to Boston around days on the trail. I imagine groups of people new to long-distance hiking (many of whom have joined Miles’ guided walks) treating it as a training ground. Perhaps pop-up ‘campsites’ – community halls, outdoor associations, local parks, nature-loving Couchers.org hosts – could provide checkpoints? 

Not everybody needs to treat the trail as an odyssey, of course – just as dog walkers, day hikers, and all manner of folk frequent sections of much longer backcountry trails. People might gradually stitch different sections together, or simply stay put and strike up the odd conversation with a passing walker. In their own ways, they will all be helping to tell a new story.