Imagine stepping off a train or bus at dawn one bright morning, and setting off on a hike through public parks, urban forests, community gardens, and residential neighborhoods. In 2022, just a couple of years after the Covid-19 pandemic underscored the beauty and social power of city green space, a group of us in Boston created the Walking City Trail: a 27-mile trail connecting some of the most immersive naturalistic and built environments in Boston for a scenic journey from the Neponset River to the Bunker Hill Monument.

It started when Miles Howard , a journalist and hiking guidebook author, read an article in National Geographic about San Francisco's Crosstown Trail. The creators of this gorgeous 17-mile urban hiking trail connected pre-existing park paths and sidewalks to take hikers on a ramble across the city's hills and canyons.
While the Crosstown Trail isn't physically marked, free maps and written trail directions and regular public transit connections make the trail easily accessible. Splitting the trail into two segments over one weekend, Miles saw a side of SF that he'd never experienced before. And the takeaway hit him in the airport, on the way home. Boston needed a trail like this. With expansive parks and urban wilds, lots of pedestrian infrastructure, and two of America's most well-known historic trails—the Emerald Necklace and the Freedom Trail—Boston is ideally positioned to host bigger, longer urban hiking trails.
So what does it take to "build" an urban trail like this? A lot of time poking around city parks and forests. A solid GPS app. And an enduring passion for sniffing out the most scenically interesting ways to walk from one urban green space to the next destination.
While the Crosstown Trail isn't physically marked, free maps and written trail directions and regular public transit connections make the trail easily accessible. Splitting the trail into two segments over one weekend, Miles saw a side of SF that he'd never experienced before. And the takeaway hit him in the airport, on the way home. Boston needed a trail like this. With expansive parks and urban wilds, lots of pedestrian infrastructure, and two of America's most well-known historic trails—the Emerald Necklace and the Freedom Trail—Boston is ideally positioned to host bigger, longer urban hiking trails.
So what does it take to "build" an urban trail like this? A lot of time poking around city parks and forests. A solid GPS app. And an enduring passion for sniffing out the most scenically interesting ways to walk from one urban green space to the next destination.

The first maps and directions for the Walking City Trail were launched in June of 2022, as an open invitation for Boston to try hiking across the city. It didn't take long for Boston residents and visitors to answer the call. Guided section hikes along the trail, co-organized with Boston City Councilor Kendra Lara and Mothers Out Front sparked ideas for how the "WCT" could be expanded to include even more immersive green (and blue) spaces. Two of the earliest WCT group hikers, Matthew Broude and Jules Murdza stepped up as fellow trail builders, once the trail re-routes began. In 2023, the Walking City Trail route was finalized.
By demonstrating that you can go for a great hike in the middle of a city, the Walking City Trail is more than a trail―it's an idea that can be replicated in more urban environments across the U.S. and around the world. Some call this approach to trail-making the Instant Urban Trail model. Granted, "instant" usually means more like 6-12 months: especially if an urban trail route is revised and finished by community consensus. But at a time when hiking is soaring in popularity and when historic structural barriers to hiking are finally being recognized, more hiking venues are sorely needed, and cities are ready to provide.
But don't just take our word for it. Come take a hike in "America's Walking City" and give the WCT shot today! Hike it in sections. Split it in half over a weekend. Or traverse the whole thing in one day. (It's only one mile longer than the Boston Marathon.) And please do get in touch if you have questions or would like to get directly involved with trail projects. Click here to learn more about how you can support the Walking City Trail and Boston's many green spaces.
But don't just take our word for it. Come take a hike in "America's Walking City" and give the WCT shot today! Hike it in sections. Split it in half over a weekend. Or traverse the whole thing in one day. (It's only one mile longer than the Boston Marathon.) And please do get in touch if you have questions or would like to get directly involved with trail projects. Click here to learn more about how you can support the Walking City Trail and Boston's many green spaces.