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The Walking City Trail in Boston: How to Hike 25 miles through the city while finding hidden gems

Anyone who has heard of Boston’s new 25-mile-long hiking trail – crossing nature reserves and parks, trekking over water features and climbing 40-foot cliffs and climbing to the final peak – can be forgiven for thinking that it sounds like one. The White Mountain Trail is worth the multi-day backcountry adventure.

In fact, the trail passes through the city of Boston and crosses the city streets and landmarks on the city’s 14-neighborhood tour within a quarter mile of Fenway Park, Beacon Hill, Faneuil Hall and TD Garden.

The Walking City Trail, Boston’s new draw for outdoor recreation, is an attempt to redefine what hiking is.

A Boston freelance journalist, longtime hiker and outdoor enthusiast, but a self-described “city man at heart” – the trail was conceived by Miles Howard – his trip across the San Francisco Crosstown Trail proved that a hiking trail could exist. An urban environment.

“It was a year of COVID and we were confined to home for a while,” Howard said. “It was customary for me to walk for a few miles to clear my head, but walking around the city during the epidemic became like hiking.

Baker Beach and the Golden Gate Bridge

Baker Beach, with its seamless view of the Golden Gate Bridge, is one of the final stops on San Francisco’s Crosstown Trail. Those who go to the beach will be photographed on August 15, 2020. (Photo by Liu Guangwan / China News Service via Getty Images).China News Service by Getty Ima

The 17-mile jaunt across San Francisco at the Crosstown Trail, he said, “is as scenic and cardiovascular as going to the White Mountains.”

Upon his return, Howard began mapping the Boston replica of the Bay Area into a city hiking trail.

The Walking City Trail, which opened last Thursday, is detailed at, where Howard posted his detailed directions, maps, notes and photos for prospective hikers. In addition to the directions, they provided packing tips, trial conditions and tips, tips for accessing the trail through public transport, and food and beverage options along the route. All are available for free.

Walking City Trail

The Walking City Trail’s website is a 25-mile hiking route through the city and green spaces of Boston. (Miles Howard).

Mapping the trail in full detail took three full walk-throughs, Howard said.

He chose specific turns to give hikers a glimpse of some of Boston’s hidden gems – the abandoned bear cages at Franklin Park, the underground Stony Brook that runs down the city.

But Howard wanted to give hikers the sense that this was a true hiking trail. In addition to several notable uphills – including Howard’s final climb to Bunker Hill, the trail’s “Mount Katahdin, agreed to the northern terminus of the Appalachian Trail – he sought stairs and other small slopes to provide a hiking experience 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 it a little more difficult and adventurous than crossing from Point A to Point B. The challenge is finding the little things that interest people.”

Walking City Trail

Map Park for the second section of the Walking City Trail in Boston. The path shown here goes from the Arnold Arboretum to Franklin Park to the Jamaica Pond. (Miles Howard).

Here are three reasons Howard thinks Boston City is best suited for hikers.

“We already have a set of city trails here,” he said, pointing to the city’s Emerald Necklace and Freedom Trail. “You can take a 7-mile hike from Franklin Park to Boston Common via the Emerald Necklace or hike the Freedom Trail where thousands of people hike each year.”

Boston has a full set of other existing green spaces spread throughout the city, including public parks and 29 urban wildlife – natural oasis encircles the city. Some of them, such as Jamaica Plain’s Neera Rock, appear on the trail.

Walking City Trail

The Walking City Trail, the brainchild of Miles Howard, redefines what hiking is. The 25-mile, urban hiking trail traverses 14 Boston neighborhoods, making it even more of an interest for tired hikers by visiting green spaces, landmarks and plenty of uphill terrain. (Will Catcher / MassLive).

Ultimately, “We have a fairly stable sidewalk here and infrastructure that a lot of cities don’t have,” Howard said. “It’s very rare that you find yourself walking on the shoulder of a road.”

Almost the entire trail exists in pedestrian-only areas, save the singular point where pedestrians cross the road without a crosswalk.

Beginning on the Harvest River bridge between Milton and Mattelpan, the trail runs through Boston’s south and into Hyde Park, where it snakes through residential neighborhoods, the greenery of Sherin Woods and the Stony Brook Reservation.

As hikers slowly escape the bustle of the city road in the nature reserve, they ascend to the first vista of the trail – a view of the Boston skyline, where they soon hike. The route then descends on Washington Street and into Roselindale Village.

Harvest River Bridge

Harvest River Bridge, the southern end of the Walking City Trail, a 25-mile urban hiking trail in Boston. (Courtesy of Miles Howard).

From there, hikers head to the Arnold Arboretum, Harvard University’s traditional outdoor botanical garden and free public park. The trail then leads to the Bussy Brook Meadow Route and the Southwest Corridor Greenway to Franklin Park, where hikers enter the “wilderness” in the city’s largest public park. There they find stone stairs, streams, and cages that formerly held the bears of Franklin Park.

It then returns to the city center, where the trail weaves through the Jamaica plains along the Jamaica Pond. The Neera Rock follows the Emerald Necklace through Olmsted Park before peeling into the Urban Wild, where a house-sized rock is dropped in the middle of the Jamaica Plain. After climbing Parker Hill (one of the best views of the route, Howard said), the trail crosses the riverfront, where it retraces the Emerald Necklace, crosses Fenway Park and lists the course to the Charle River Esplanade.

Walking City Trail

The Walking City Trail, the brainchild of Miles Howard, redefines what hiking is. The 25-mile, urban hiking trail traverses 14 Boston neighborhoods, making it even more of an interest for tired hikers by visiting green spaces, landmarks and plenty of uphill terrain. Howard is depicted describing the section of trails in the Boston Public Garden. (Will Catcher / MassLive).

The final section of the trail covers about five and a half miles, strikes Boston Public Garden and Common, passes Beacon Hill, enters Chinatown, follows the Rose Kennedy Greenway to the Waterfront and the North End, and finally crosses. The Zakim Bridge to Charlestown and the foot bridges next to the TD Garden. The final push up of Bunker Hill revolves around the Walking City Trail, about 25 miles from the South Terminus at Matapan.

Howard said the trail not only opens up hikers’ imaginations about what “hike” is, but hopes it can open hiking for people who can’t or can’t participate.

“When we think of backcountry hiking, access to a car is an enormous economic and logistical barrier for many people. “Every city may not be able to do that, but it’s a really unused resource.”

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