Help Us Launch Boston's City On The Hills Trail

Boston's Walking City Trail began in 2022 from a singular question. What if you could walk from the Neponset River to the Bunker Hill Monument, through parks, gardens, wetlands, and urban forests? That question led to the communal creation of a 27-mile urban trail that showcases some of the city's most immersive green spaces *and* the beautiful city neighborhoods that connect them. But why stop at one trail? Why not create a network of urban trails linking the places we call home with the greenery where we find peace?

On Earth Day, the Walking City Trail creators will launch Boston's next cross-city trail. The City On The Hills Trail will run 31 miles from West Roxbury's Millennium Park to Castle Island in Southie, visiting more than 40 green spaces in nine of Boston neighborhoods that are not part of the Walking City Trail route! Just like the WCT, the City On The Hills Trail is accessible by way of public transit and designed to be hiked in five segments. (Or in one really long day.)

This past winter, Walking City Trail founder and lead organizer Miles Howard led a series of public surveying walks along the proposed City On The Hills Trail route, attended by over 200 Boston residents and visitors; a collective testing and workshopping of the trail, which is now ready for its world debut on April 22nd. Soon, the Walking City Trail will start to become a collection of literal grassroots trails.

Between web hosting, materials, and labor costs, the projected expense of launching the new trail and sustaining the materials for both trails is $1,000. If we can hit this goal, we'll be in the clear. If we surpass the goal, any additional donations will be set aside to cover the same recurring costs for future years, in addition to labor and materials for forthcoming trail projects such as creating a platform for the public to propose (and test-walk) additional Boston trails. With your generous support, the Walking City Trail and the City On The Hills Trail can flourish in 2025 and beyond, while also paving the road for development of the next cross-city trails.

To learn more about the Walking City Trails, you can visit the official trail website. (The City On The Hills will go live on Earth Day, via the same URL.) And if you're active on Instagram, you can learn more about the trail and upcoming events by following @WalkingCityTrail.