{"id":198218,"date":"2025-03-12T09:46:29","date_gmt":"2025-03-12T16:46:29","guid":{"rendered":"https:\/\/www.rei.com\/blog\/?p=198218"},"modified":"2025-05-15T18:15:58","modified_gmt":"2025-05-16T01:15:58","slug":"walking-city-trail-boston","status":"publish","type":"post","link":"https:\/\/www.rei.com\/blog\/hike\/walking-city-trail-boston","title":{"rendered":"A Walk in the (Urban) Park"},"content":{"rendered":"\n

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\u2019t 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?<\/p>\n\n\n\n

Yet one after the other, walkers materialized from public buses and parked cars and joined him on the small green in southwest Boston. He\u2019d 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\u2019s brainchild, the Walking City Trail\u2014one of the country\u2019s unlikeliest thru-hikes.<\/p>\n\n\n\n

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<\/a>, 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\u2019s become a beacon for the growing urban hiking movement.<\/p>\n\n\n\n

As more people gathered on that steamy summer day, curious where the trail might take them, Howard\u2019s path, at least, was suddenly clear to him. \u201cThat showed me that leading people on a long walk through urban territory can actually be an event that brings out our gregarious side,\u201d the REI Co-op Member says. \u201cI knew we were on to something.\u201d<\/p>\n\n\n\n

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Urban thru-hiking advocate Miles Howard, REI Co-op Member since 2010. Photo credit: George Heinrichs<\/em><\/figcaption><\/figure>\n\n\n\n
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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\u2019s 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\u2019s footsteps, Howard spent his summers during college flying back from the University of Southern California each June to join the seasonal hut crew.<\/p>\n\n\n\n

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.<\/p>\n\n\n\n

Stuck in the city and carless during COVID-19\u2019s 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.<\/p>\n\n\n\n

\u201cRather than taking an aimless stroll in the park during those first months of 2020, I would look at maps of the city and say, \u2018Okay, I want to go on an expedition to a landmark I\u2019ve never been to before,\u201d he remembers, \u201cand I want to get there by going through a park I\u2019ve never seen before.\u2019\u201d<\/p>\n\n\n\n

Back in his apartment in Boston\u2019s Jamaica Plain neighborhood, the blond-bearded urban expeditioner started a new routine: pack like he was spending a day in the Whites\u2014snacks, sunscreen, clothes for the elements<\/a>\u2014and 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.<\/p>\n\n\n\n

More importantly, he realized that exploring urban green spaces gave him a high similar to his time on the trail.<\/p>\n\n\n\n

\u201cI feel like there are a lot of recreational sports where there\u2019s an intensity to the activity that demands a lot of cognitive power,\u201d he explains. \u201cWith hiking or walking, it\u2019s simple enough in most places that I feel like there\u2019s room for my mind to wander.\u201d<\/p>\n\n\n\n

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>\u2014a 17-mile urban route connecting pre-existing trails from Candlestick Point out to the cliffs at Lands End\u2014Howard set out on a \u201cfield trip\u201d to experience the trail firsthand in 2022. Along the way, he realized he\u2019d been thinking too small. He didn\u2019t need a few short walks around his neighborhood, but a thread that connected them all\u2014and so did Boston.<\/p>\n\n\n\n

\u201cIt 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,\u201d says Howard. \u201cCuration itself can be a form of trail-building.\u201d<\/p>\n\n\n\n

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.<\/p>\n\n\n\n

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The 27-mile Walking City Trail winds through Boston’s parks, gardens and residential neighborhoods. <\/strong>Photo credit: Miles Howard<\/em><\/figcaption><\/figure>\n\n\n\n

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\u2019s 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. \u201cThere are many ways that [urban hiking] runs parallel with traditional hiking, but what\u2019s fun are the divergence points,\u201d explains Howard. \u201cYou can stop at a good Cuban restaurant or a show at an art gallery. You can\u2019t do that in a normal hiking scenario.\u201d 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.<\/p>\n\n\n\n

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\u2019d 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\u2014a sort of social pollination that carried through the rest of the day.<\/p>\n\n\n\n

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. <\/p>\n\n\n\n

\u201cI just don\u2019t think a trail is likely to survive unless the community wants it to,\u201d says Howard. \u201cThe 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\u2019s why buy-in from community is especially important.\u201d<\/p>\n\n\n\n

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Photo credit: Miles Howard<\/em><\/figcaption><\/figure>\n\n\n\n

Momentum around the trail has grown in recent years, and Howard\u2014often clad in sunflower-laden board shorts, a cut-off Godzilla T-shirt and a headband (plus hiking boots, of course)\u2014still is a mainstay on the route. He wants to show that a day on the trail can be accessible for everyone, and he\u2019s adamant that hiking isn\u2019t homogenous. A city hike may be the best place to celebrate that.<\/p>\n\n\n\n

\u201cI think hiking is goofier than we give it credit for,\u201d Howard maintains. \u201cThat really becomes apparent in the city. There\u2019s such a clash of people, activities and environments.\u201d<\/p>\n\n\n\n

Since the Walking City Trail debuted, other urban trails have appeared around the country, such as Denver\u2019s Orbital Trail and Seattle\u2019s Olmsted 50 Trail (an ode to landscape architect and creator of New York City\u2019s Central Park, Frederick Law Olmsted). More are in the works.<\/p>\n\n\n\n

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\u2019t out of the question, he says, but he isn\u2019t in a hurry to put out a half-baked sequel.<\/p>\n\n\n\n

Instead, he\u2019s keeping in mind the lessons learned on that first group walk in 2022. Toward the end of the walk, one of Howard\u2019s newfound trail friends pulled him aside. The experience, the friend said, had shown him a new urban perspective\u2014that adventure was just a walk away.<\/p>\n\n\n\n

\u201cI was really impressed by that mental leap,\u201d says Howard. The City Walking Trail, he says, \u201cunlocked the possibilities of the city.\u201d<\/p>\n\n\n\n

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Photo credit: Miles Howard<\/em><\/figcaption><\/figure>\n\n\n\n

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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\u2019t worried about the temperature. Instead, he was worried about who […]<\/p>\n","protected":false},"author":30740,"featured_media":199561,"comment_status":"open","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"_jetpack_memberships_contains_paid_content":false,"footnotes":""},"categories":[387],"tags":[1826,109,520],"internal-tag":[2011],"class_list":["post-198218","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-hike","tag-boston","tag-member-stories","tag-urban-hiking","internal-tag-home-secondary"],"parsely":{"version":"1.1.0","canonical_url":"https:\/\/rei.com\/blog\/hike\/walking-city-trail-boston","smart_links":{"inbound":0,"outbound":0},"traffic_boost_suggestions_count":0,"meta":{"@context":"https:\/\/schema.org","@type":"NewsArticle","headline":"A Walk in the (Urban) Park","url":"http:\/\/www.rei.com\/blog\/hike\/walking-city-trail-boston","mainEntityOfPage":{"@type":"WebPage","@id":"http:\/\/www.rei.com\/blog\/hike\/walking-city-trail-boston"},"thumbnailUrl":"https:\/\/www.rei.com\/blog\/wp-content\/uploads\/sites\/4\/2025\/03\/HERO-IMG_4878.jpg?resize=150%2C150","image":{"@type":"ImageObject","url":"https:\/\/www.rei.com\/blog\/wp-content\/uploads\/sites\/4\/2025\/03\/HERO-IMG_4878.jpg?fit=2000%2C1500"},"articleSection":"Hike","author":[{"@type":"Person","name":"Ever Meister"}],"creator":["Ever Meister"],"publisher":{"@type":"Organization","name":"Uncommon Path \u2013 An REI Co-op Publication","logo":""},"keywords":["boston","rei co-op member stories","urban hiking"],"dateCreated":"2025-03-12T16:46:29Z","datePublished":"2025-03-12T16:46:29Z","dateModified":"2025-05-16T01:15:58Z"},"rendered":"