Miles Howard nervously shifted in his well-worn hiking boots. He had months of training and felt more than prepped for the rigors of the trail. The weather might have foiled him on two previous attempts, but on that humid July morning in 2022, he wasn’t worried about the temperature. Instead, he was worried about who else was going to show up. After all, who starts a group hike next to a nail salon?
Yet one after the other, walkers materialized from public buses and parked cars and joined him on the small green in southwest Boston. He’d seen the chatter about urban hiking blowing up his Twitter feed. But to see it happen in real life was a different thing entirely. Soon, 10 people had arrived, clad in varying interpretations of athletic garb and equipped for a day trying out Howard’s brainchild, the Walking City Trail—one of the country’s unlikeliest thru-hikes.
Urban hiking trails have appeared from Denver to Seattle in recent years, and in Boston, Howard and a crew of volunteers have challenged the notion of how we get outside with the meandering, 27-mile south-to-north Walking City Trail, established in 2022. The trail could transform a pursuit historically reserved for undeveloped places by connecting public green spaces, neighborhoods, and even natural and manmade waterways into a full-blown outdoors experience. In just two years, it’s become a beacon for the growing urban hiking movement.
As more people gathered on that steamy summer day, curious where the trail might take them, Howard’s path, at least, was suddenly clear to him. “That showed me that leading people on a long walk through urban territory can actually be an event that brings out our gregarious side,” the REI Co-op Member says. “I knew we were on to something.”
Howard grew up outdoors. Raised in Winchester, Massachusetts, along the suburban northern edge of Boston, the now-36-year-old spent his early years romping around the wooded trails of the 2,200-acre Middlesex Fells Reservation. This wilderness area was the perfect incubator for a curious kid from the suburbs. Soon, after-school jaunts turned into weekend trips to the nearby White Mountains of New Hampshire. Howard’s mother and grandfather had spent significant time in the same mountains, and his maternal great-grandfather, Forbes McGregor, was said to be one of the first caretakers in the Appalachian Mountain Club hut system in the early 1900s. Following in McGreggor’s footsteps, Howard spent his summers during college flying back from the University of Southern California each June to join the seasonal hut crew.
After college Howard returned to Boston and worked as a journalist for local newspapers. Weekends, though, led him right back to mountain trails he found both fascinating and deeply peaceful.
Stuck in the city and carless during COVID-19’s onset, Howard was cut off from his weekend pathfinding. Suddenly, he lacked the outdoor outlet he relied on. Faced with pandemic uncertainty, he did what most lost adventurers would do: He plotted a course.
“Rather than taking an aimless stroll in the park during those first months of 2020, I would look at maps of the city and say, ‘Okay, I want to go on an expedition to a landmark I’ve never been to before,” he remembers, “and I want to get there by going through a park I’ve never seen before.’”
Back in his apartment in Boston’s Jamaica Plain neighborhood, the blond-bearded urban expeditioner started a new routine: pack like he was spending a day in the Whites—snacks, sunscreen, clothes for the elements—and follow a mapped-out route. Soon his walks included visits to four or five favorite nearby parks. Then he added new-to-him green spaces. His mileage crept steadily higher.
More importantly, he realized that exploring urban green spaces gave him a high similar to his time on the trail.
“I feel like there are a lot of recreational sports where there’s an intensity to the activity that demands a lot of cognitive power,” he explains. “With hiking or walking, it’s simple enough in most places that I feel like there’s room for my mind to wander.”
As he began finding his footing on shorter, city-bound routes, he was ready for more. Months after reading about San Francisco’s Crosstown Trail—a 17-mile urban route connecting pre-existing trails from Candlestick Point out to the cliffs at Lands End—Howard set out on a “field trip” to experience the trail firsthand in 2022. Along the way, he realized he’d been thinking too small. He didn’t need a few short walks around his neighborhood, but a thread that connected them all—and so did Boston.
“It hit me that you can not only go for an amazing hike in a city, but you can create those hiking routes without having a massive budget or background in trail-building,” says Howard. “Curation itself can be a form of trail-building.”
Blistered and sunburnt from his Crosstown trek and sitting in a San Francisco airport lounge, he pored over maps of Boston, imagining a complementary route in his hometown. By the time he landed on the East Coast, he already had three full outlines. The Walking City Trail officially debuted later in the summer of 2022.
The Walking City Trail is broken up into four manageable sections. It crosses 17 neighborhoods, hitting green areas like the Hyde Park neighborhood, Arnold Arboretum and the Charles River Esplanade as it winds from the Neponset River Reservation to the Bunker Hill Monument. Howard’s goal was to build a unique connector that prioritized green space without ignoring the many realities of city living. As a result, the trail visits residential neighborhoods, traverses concrete and crosses the occasional road. But it also offers the unexpected along the way. “There are many ways that [urban hiking] runs parallel with traditional hiking, but what’s fun are the divergence points,” explains Howard. “You can stop at a good Cuban restaurant or a show at an art gallery. You can’t do that in a normal hiking scenario.” He also designed the trail with accessibility in mind: Segments begin and end near public transportation, for instance. A website for the trail details logistics and highlights, from bathrooms and water fountains to historical landmarks and places to grab a bite. The site also offers packing advice for a day outside.
But when Howard teased the first July hike on Twitter in 2022, these considerations and accommodations were in their infant stages. He needed to test his theory. Though he’d seen a decent amount of interest online, it was yet another thing for people to show up in person. But they did. The group headed off. Within a few miles, hikers began pointing out landmarks and sharing stories—a sort of social pollination that carried through the rest of the day.
Despite months of reading maps and walking his city for research, Howard quickly realized it was the people walking alongside him, not the infrastructure, that gave the trail life. Soon, volunteers jumped onboard to not only help spread the word, but to improve the trail itself. Eventually, volunteer stewards and trail builders helped extend the trail to its current 27-mile length and added temporary, laminated signage along the way.
“I just don’t think a trail is likely to survive unless the community wants it to,” says Howard. “The reality is that not everyone in a city has access to the best and most immersive green spaces, and I think popularizing walking areas that bridge these routes has a lot of potential to help. That’s why buy-in from community is especially important.”
Momentum around the trail has grown in recent years, and Howard—often clad in sunflower-laden board shorts, a cut-off Godzilla T-shirt and a headband (plus hiking boots, of course)—still is a mainstay on the route. He wants to show that a day on the trail can be accessible for everyone, and he’s adamant that hiking isn’t homogenous. A city hike may be the best place to celebrate that.
“I think hiking is goofier than we give it credit for,” Howard maintains. “That really becomes apparent in the city. There’s such a clash of people, activities and environments.”
Since the Walking City Trail debuted, other urban trails have appeared around the country, such as Denver’s Orbital Trail and Seattle’s Olmsted 50 Trail (an ode to landscape architect and creator of New York City’s Central Park, Frederick Law Olmsted). More are in the works.
In the meantime, Howard and local government officials are working to fortify the progress he and Boston’s urban hiking contingent have already built. They are lobbying for permanent funding for future trail projects and maintenance. A second Walking City Trail isn’t out of the question, he says, but he isn’t in a hurry to put out a half-baked sequel.
Instead, he’s keeping in mind the lessons learned on that first group walk in 2022. Toward the end of the walk, one of Howard’s newfound trail friends pulled him aside. The experience, the friend said, had shown him a new urban perspective—that adventure was just a walk away.
“I was really impressed by that mental leap,” says Howard. The City Walking Trail, he says, “unlocked the possibilities of the city.”
