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A 27-mile community-made trail brings urban hiking to Boston

The Walking City Trail, spanning 17 neighborhoods, marries the city’s green spaces and urban landscapes to create an immersive experience for locals and tourists.

Chart an urban hike through Boston’s neighborhoods
WATCH: Correspondent Alysa Guffey offers a new kind of hiking adventure that journeys through the city neighborhoods of Boston.

Like many fresh ideas in recent years, the inspiration for an official urban hiking trail in Boston came during the COVID-19 pandemic, said Miles Howard, who would go on increasingly longer walks to feel the “escape of a hike” without leaving Greater Boston.

“We really had to make the most of what we had here in our backyard,” Howard, a freelance journalist who has written for The Boston Globe, said of his treks in 2020. “These adventures became kind of a pastime during the first year of the pandemic.”

Then, Howard took a hike on the Crosstown Trail, which connects opposite areas of San Francisco through hidden trails, public parks, and shopping corridors. Upon returning to Boston, Howard set out to create a similar path that would use existing parks, streets, and landmarks in the city.


The result was the Walking City Trail, an unofficial trail mapped by Howard through existing walkways that stretches 27 miles across 17 neighborhoods from its origin in Mattapan to its finish at Bunker Hill.

At its core, Howard said urban hiking is defined less by location and more by intention.

“It’s trying to find the most scenically interesting way to get from one spot to an eventual destination that really showcases the full beauty and oddity of a landscape,” he said.

To make the marathon-length course more manageable to complete in chunks, creators split the Walking City Trail into four sections, Howard said.

At the entrance to the Edgewater Greenway in Mattapan, where the 27-mile trail begins, a mural depicts a farmer.John Tlumacki/Globe Staff

Spanning 8.3 miles, the first section starts in Mattapan at the Neponset River, heads south into Hyde Park, and winds north before ending in Roslindale Village. The second section picks up at the entrance of the Arnold Arboretum before winding through Jamaica Plain.

Section three weaves through the neighborhoods of Mission Hill, Longwood, and the Fenway before ending at the Charles River. The closing segment threads through Boston Common, Chinatown, and the Leather District before finishing with a walk along the Harbor and a summit of Bunker Hill.


Hikers can enjoy elevated views of the Boston skyline in several locations along the trail, including atop Kevin Fitzgerald Park in Mission Hill, at the Arnold Arboretum in Jamaica Plain, and while descending into Roslindale Village.

Although Howard spearheaded the project, the final version of the Walking City Trail was made with feedback from the public on community hikes in 2022 led by Howard and Councilor Kendra Lara, chair of the Environmental Justice, Resiliency, and Parks Committee. Howard said community hikes were vital to bring the trail to life.

“No trail can ever be a solo project forever if it wants to endure,” Howard said. “The community has to take ownership of it.”

A woman walks through Peters Hill in the Arnold Arboretum on June 23, 2023.John Tlumacki/Globe Staff

One notable change made to the trail during community feedback was the trajectory of section four, which originally did not go alongside the harbor and seemed almost like “a commute,” said Matthew Broude, a downtown Boston resident who helped workshop the trail last summer.

In pitching a change to the trail’s path, Broude said he envisioned ways to delineate the path through downtown Boston — an area of the city many people walk through daily. The updated section incorporates the Harborwalk to open up the hiking space, Broude said, and allow for views of the path ahead and the path behind.

“It’s kind of like seeing where you’re heading later, and then you kind of get this experience of seeing where you came from before,” Broude said.


Another aspect of trail building is equity, Howard said, as green spaces are often disproportionately near wealthier communities, which can lead people from other communities to feel unwelcome on public paths in certain areas. He noted that the safety of hikers should be considered when mapping out trails for public use.

“People have to feel comfortable” using community trails, said Anita Berrizbeitia, a landscape architecture professor at Harvard University who is interested in public landscapes. “Otherwise, they don’t use them.”

A smoke tree at the top of Peters Hill in the Arnold Arboretum is one of many plants hikers can see along the Walking City Trail.John Tlumacki/Globe Staff

Berrizbeitia added that visible trails can create a sense of shared culture, allowing more people to inhabit paths in the city.

“We can have delicate moments of nature juxtaposed with these concrete blocks, but people wouldn’t know to go out and see them,” Berrizbeitia said.

Currently, the Walking City Trail is only accessible via a digital map online. For the project to become an official attraction, the City of Boston would need to pass a resolution in support, and then the Parks Department would have to recognize it as an official trail, Lara said. Permanent signage marking the trail would come after, she added.

In the meantime, Howard and a small group of hikers are installing temporary signs along the trail to advertise and track trail usage this summer. The signs will include QR codes to information about the trail, Howard said.

The view of the Boston skyline from the top of Peters Hill in the Arnold Arboretum is one of several places along the Walking City Trail that hikers can stop to take in the city.John Tlumacki/Globe Staff

When hiking the Walking City Trail, Howard recommends bringing water and wearing comfortable shoes. But, he emphasized that, unlike remote hiking, urban hiking allows for greater flexibility to refuel along the way.


“One thing I really love about urban hiking as opposed to the backcountry is because you’ve got public transit and other options for getting on and off the trail, it enables people to activate it in whatever way makes the most sense for them ultimately, even if it’s just going out for a half mile jog through some unfamiliar place,” Howard said.

Community members can attend guided hikes this summer on Aug. 12 and Aug. 26. Guided hikes will cover sections three and four, respectively.

Alysa Guffey can be reached at Follow her @AlysaGuffeyNews.