JP Observer: Take a Hike Through JP, Boston Along a Unique Urban Trail

Special to the Gazette

A new way to socialize, get some exercise that’s not strenuous, and become immersed in Boston green spaces is being unveiled this summer by the Jamaica Plain man who invented it.

Miles Howard created what’s called “The Walking City Trail,” 25 miles divided into four sections across 14 Boston neighborhoods, including JP.

Howard has led the first two guided tours this summer, one section at a time, and people say they have enjoyed it despite the heat. The next tour is scheduled for Aug. 27. People are also encouraged to hike the trail on their own if they want any time.

JP resident Rebeca Plank, who went on both tours and plans to do the third, said she saw “a lot of places she’d never ever seen before.” She mentioned the view of the Harbor Islands from Parker Hill and White Stadium and the bear cages in Franklin Park.

Plank said the hike isn’t strenuous, though there are some staircases. “There are plenty of places to stop and rest,” she said

She added that there were people of “all body types” on the walks, and people came back to the second one. It was Plank who contacted me about the Walking City Trail. She had first seen it on Facebook.

Howard is seeking community input about all aspects of the trail—

which stretches from the Neponset River in Mattapan to the foot of the Bunker Hill Monument in Charlestown—welcoming suggested improvements or additions from the community.

Amazingly, all sections of the urban trail, about the same length as the Boston Marathon route, were drawn up this past March by Howard to be accessible by public transportation. The green space routes also feature frequent possible stopping points for food, drink, arts and culture, as well as restrooms.

The Walking City Trail can be entered or exited at any point, and with the nearness to public transit, is accessible to people without cars, unlike backcountry hiking, Howard pointed out.

Section 2 of the trail is set in JP and starts at what the website description called the “arbor paradise” of Arnold Arboretum, goes down the Southwest Corridor Park into “the wilderness” of Franklin Park, then goes through a “hidden woodland” to finish this section at the Jamaica Pond boathouse.

In an interview earlier this month, Howard touted Section 3 to Jamaica Plainers. He pointed out the huge puddingstone boulders and “one of the best Boston views” from the summit of Parker Hill in Mission Hill. NIRA Rock in northern JP is also in Section 3.

Howard, a freelance writer, came up with the trail idea during the first year of the pandemic. Having hiked in the wilderness for years in New England’s backcountry, he decided to hike to the tower in Fort Hill in Roxbury from downtown JP in December, 2020.

Hiking had become his “tonic for pandemic stress,” Howard wrote in an article about the trail for WBUR’s Cognoscenti in June. He said he wondered after the exhilarating walk to Fort Hill: “Can you go hiking in the middle of a city?”

After reading about the Crosstown Trail in San Francisco in National Geographic, he flew to the Bay Area and tried out the trail devised by several residents. He spent two days walking the 17 miles on a route “through the city’s best parks and green spaces.”

Howard said Boston is called “America’s Walking City” for good reason. He praised Frederick Law Olmsted’s Emerald Necklace as “arguably one of the oldest urban hiking trails in America” and mentioned other walks as well.

Studying maps of parks and urban wilds in Boston early this year, he also used Google Earth and AllTrails app to create a guide “through the urban green spaces that are lush and wild enough to make you forget that you’re in the middle of a city.”

Then he did the important work of hiking the trail he imagined, looking for features that might prompt a modification.

When he leads tours, Howard emphasized, he’s narrating only about 20 percent of the time. He would like to have community input all along. Plank suggested to have more water fountains and said some hikes after a while could feature native plants or art along the way.

“Urban hiking is the next frontier,” Howard said in the interview. He said he feels like The Walking City Trail project is a “post-pandemic pioneer” where “The trail concept is applied to urban green space.”

Howard said his urban trail project is in its beta phase. He has talked to city officials and he wants to work with a cartographer in the future.

“At heart I am a city person,” he said. Looking back now, he added, he could see that, “The urban hike idea was slowly hurtling toward me.”

Right now, he said, The Walking City Trail is a “backyard community effort.” He plans to apply for grants in the future and plans to do more guided tours in the fall.

For lots of both inspirational and useful information about taking a hike along the trail, go to How to obtain trail maps—digital and paper—is explained. Descriptions of trail conditions, what to pack for the hike, and transportation connections are there. How to support the project with a donation or otherwise, is also described. Best of all, people can also sign up for the newsletter or contact Howard via the website.

Showing respect for the existing green space in Boston, the website says: “An urban trail like the Walking City Trail is nothing without a thriving ecosystem of urban green spaces. If you’d like to help keep Boston’s paths in solid shape for the next generations of urban hikers, please consider donating some time and labor to any of these local organizations” and provides links to 16 of them, including: Arnold Arboretum, Boston Park Advocates, City of Boston Urban Wilds Program, Franklin Park Coalition, Southwest Corridor Park Conservancy, The Emerald Necklace Conservancy, Friends of NIRA Rock, and WalkBoston.

Asked why she likes The City Walking Trail so much, Plank was enthusiastic. “I love Boston,” she said, “especially JP.”

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