Boston’s Walking City Trail: How to hike 25 miles through the city while discovering hidden gems –


The Walking City Trail, the brainchild of Miles Howard, is redefining what hiking is. Over 25 miles, the urban hiking path traverse 14 Boston neighborhoods, visiting green spaces, landmarks and enough uphills to keep even a jaded hiker interested. Howard is pictured ascending a section of the trail in the Boston Public Garden. (Will Katcher/MassLive).
Someone hearing about Boston’s new 25-mile-long hiking path — crisscrossing nature reserves and parks, trekking over water features and past 40-foot boulders, and culminating in an uphill push to a final summit — could be forgiven for thinking it sounded like a White Mountain trail worthy of a multi-day backcountry adventure.
In fact, the trail traverses urban Boston, and it passes at different points within a quarter-mile of Fenway Park, Beacon Hill, Faneuil Hall and TD Garden as it winds through city streets and landmarks on a 14-neighborhood tour of the city.
The Walking City Trail, Boston’s newest draw for outdoor recreation, is an effort to redefine what hiking means or even is.
The trail is born from the imagination of Miles Howard — a Boston freelance journalist, longtime hiker and outdoors enthusiast, but self-described “city person at heart” — who said his trip across San Francisco’s Crosstown Trail proved that a hiking trail could exist in an urban environment.
“It was Year One of COVID and we’d been confined to home for some time,” Howard said. “It was customary for me to go out walking for a few miles to clear my head. But during the pandemic walking around the city became more like urban hiking.”
Baker Beach, with its unobstructed view of the Golden Gate Bridge, is one of the final stops on San Francisco's Crosstown Trail. Beachgoers are photographed on August 15, 2020. (Photo by Liu Guanguan/China News Service via Getty Images).China News Service via Getty Ima
The 17-mile jaunt across San Francisco on the Crosstown Trail, he said, was “as scenically and cardiovascularly exhilarating as going to the White Mountains.”
Upon his return, Howard began meticulously mapping out a Boston counterpart to the Bay Area city’s urban hiking path.
The Walking City Trail, open as of last Thursday, is detailed on, where Howard posted his detailed directions, maps, notes and photos for prospective hikers. Alongside the directions, he provided packing suggestions, trail conditions and advice, suggestions for accessing the trail by public transit, and food and drink options on the route. All are available for free.
The website of the Walking City Trail, a 25-mile hiking path through Boston's urban and green spaces. (Miles Howard).
Mapping the trail in full detail took three full walk-throughs, Howard said.
He chose specific turns in order to give hikers a look at some of Boston’s hidden gems — the abandoned bear cages in Franklin Park, the subterranean Stony Brook that runs beneath the city.
But Howard also wanted to give hikers the sense that this was a true hiking trail. In addition to featuring several notable uphills — including the final ascent up Bunker Hill that Howard agreed was the trail’s “Mt. Katahdin,” a nod to the northern terminus of the Appalachian Trail — he sought out stairs and other small inclines to provide the hiking feel to the city setting.
“People sometimes ask — isn’t urban hiking just walking?” Howard said. “You’re deliberately looking for destinations and features that make the route a little more rigorous and adventurous than strolling from Point A to Point B. The challenge is looking for little things that keep people interested.”
Park of a map for the second section of Boston's Walking City Trail. The path displayed here heads from the Arnold Arboretum to Franklin Park on toward Jamaica Pond. (Miles Howard).
There were three reasons Howard thought Boston would be well suited for urban hikers.
“We already have a set of urban trails here,” he said, pointing to the city’s Emerald Necklace and Freedom Trail. “You can take a 7-mile hike through the Emerald Necklace from Franklin Park to the Boston Common or hike the Freedom Trail, which thousands of people hike every year.”
Boston also has a thorough set of other existing green spaces scattered throughout the city, including public parks and 29 Urban Wilds — natural oases that dot the city in unassuming locations. Some of them, such as Jamaica Plain’s Nira Rock, appear on the trail.
The Walking City Trail, the brainchild of Miles Howard, is a redefining what hiking is. Over 25 miles, the urban hiking path traverse 14 Boston neighborhoods, visiting green spaces, landmarks and enough uphills to keep even a jaded hiker interested. (Will Katcher/MassLive).
Finally, “we have pretty consistent sidewalk here and infrastructure that a lot of cities don’t have,” Howard said. “It’s pretty rare that you find yourself walking on the shoulder of a road.”
Nearly the entire trail exists on pedestrian-only spaces, save for a singular point where hikers cross a street without a crosswalk.
Beginning on the Harvest River Bridge between Milton and Mattapan, the trail winds its way through Boston’s southern reaches and into Hyde Park, where it snakes through residential neighborhoods, the greenery of Sherrin Woods and into Stony Brook Reservation.
As hikers slowly escape the bustle of an urban street in the nature reserve, they ascend to the trail’s first vista — a view of Boston’s skyline, which they will soon hike toward. The path then descends down Washington Street and into Roslindale Village.
The Harvest River Bridge, the southern end of the Walking City Trail, Boston's 25-mile urban hiking path. (Courtesy of Miles Howard).
From there, hikers head for the Arnold Arboretum, Harvard University’s iconic outdoor botanical garden and free public park. The trail then heads on the Bussey Brook Meadow path and Southwest Corridor Greenway toward Franklin Park, where hikers enter a “wilderness” in the city’s largest public park. There they find stone stairways, streams and the cages that previously held the Franklin Park’s bears.
Then it is back into the urban city, where the trail weaves through Jamaica Plain en route to Jamaica Pond. The trail follows the Emerald Necklace through Olmstead Park before peeling off for the Nira Rock Urban Wild, where a house-sized boulder is stubbornly plunked down in the middle of a Jamaica Plain neighborhood. After a climb over Parker Hill (one of the route’s best views, Howard said), the trail hits the Riverway, where it picks back up the Emerald Necklace, heads past Fenway Park and charts a course for the Charle River Esplanade.
The Walking City Trail, the brainchild of Miles Howard, is a redefining what hiking is. Over 25 miles, the urban hiking path traverse 14 Boston neighborhoods, visiting green spaces, landmarks and enough uphills to keep even a jaded hiker interested. Howard is pictured describing a section of trail in the Boston Public Garden. (Will Katcher/MassLive).
The final section of trail is a packed roughly five-and-a-half miles, hitting the Boston Public Garden and Common, passing by Beacon Hill, entering Chinatown, following the Rose Kennedy Greenway to the Waterfront and North End, and finally crossing over footbridges next to the Zakim Bridge and TD Garden to Charlestown. The final push up Bunker Hill wraps up the Walking City Trail, nearly 25 miles from the southern terminus in Mattapan.
Howard hopes this trail can not only open up hikers’ ideas of what “a hike” is, but that it can also open up hiking itself to people who may not be inclined or able to partake.
“When we think of backcountry hiking, access to a car is an enormous financial and logistical barrier to a lot of people. By design, cities are places you don’t need a car to access. As we think about the toll that car-centric design is taking on the environment, the question of where hiking can happen will become more relevant in the years ahead,” he said. “Not every city will be able to do this, but it’s really an untapped resource.”
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