A new Boston trail is coming

...and you can help build it

Greetings, Boston.

I’ll get straight to the point. Now that we’ve had a chance to rest and recharge during some of the darkest weeks of the year, it’s time to share some big news which has been a long time coming; something that I have been alluding to for several months now.

This winter and spring, we are building a new trail across Boston. And you can help!

The Walking City Trail was initially envisioned as a singular walking route through some of Boston’s most immersive green spaces and neighborhoods. But it didn’t take long for the idea to evolve. Why stop at just one trail when you could have a network of trails, connecting every neighborhood in the city? So in late January, the next big step toward expanding the map and building that Boston trail network will begin, at last.

What you see in the screencap above is a prospective map of a new trail that will run through Boston. It will be a west to east trail from Millennium Park in West Roxbury to Castle Island in South Boston; perpendicular to the WCTs south to north trajectory. The two trails will merge around Mission Hill and The Riverway, to form a squiggly X across Boston. Just like the WCT, this new trail will be designed to take walkers into lots of beautiful city parks, preserved open spaces, and built environments. It will run through neighborhoods that are not featured on the Walking City Trail route. And the trail will also be a literal escalation—a little longer and a little more roly-poly than the WCT. The working title of the trail, which may change, is the City On The Hills Trail and the plan is to launch it on Earth Day 2025 (April 22nd) and promote it from there.

There’s a notable difference between how the City On The Hills Trail will be shaped and launched, compared to how the WCT was conceived, finessed, and cemented. In the latter case, a “rough draft” version of the trail was launched, and the wider public was invited to come and experience the trail on hikes, where we talked about how the trail could be made better. This time around, I’m hosting the public surveying hikes before the launch of the City On The Hills Trail. And the first is just 12 days away!

If you’d like to roll up your sleeves (or roll your sleeves over your gloves) and help build the City On The Hills Trail, come out and join us for any of the surveying hikes listed on the banner above. These hikes will be taking place on Saturdays, from late January to late March. Each day features two back-to-back hikes of 3-ish miles each. Together, the two hikes will cover a section of the City On The Hills Trail, which will likely be divided into five sections total. A signup form for each surveying hike will be shared via the newsletter at least two weeks before each hike. UPDATE: The signup window for the January 25th surveying hike has closed.

- These surveying hikes are different from the guided urban hikes that I’ve offered in the past. These are walking working groups in which we will go out, walk a planned route together, and discuss what’s working, what’s not, and how the route could be changed to include cool stuff nearby. As one of our earliest trail volunteers, Wyoma, said at a recent hangout, this is less of a guided hike and more of a “Make A Hike.”

- On each date, the morning hike will start at 9am and finish at a location near food and public transit. After an hour lunch break, the subsequent hike will start around 1pm from the some spot. You can come for both hikes, one hike, or a piece of a hike. And each surveying hike signup page will include info on public transit and parking.

- Because these are working group hikes, we will be on something of a schedule for each one, trying to cover 3-ish miles in 3-ish hours. However, this will become more flexible as we transition into March, with the sun going down slightly later by then.

- If you would like to come to any of these hikes, please be sure to sign up in advance! Again, each signup page will be shared via the newsletter. You’re welcome to bring along accomplices at the last minute though, and there’s no need for everyone in your group to complete a signup form. As long as one of you is signed up, we’re good. The reason why this is important is because some hikes may be rescheduled if there’s bad weather, and I would want every person or group that signed up for the hike to be able to get an email update about this change of plans; so that no one finds themselves in a snowy, empty parking lot this winter, wondering, “Where the hell is the WCT crew?”

- Lastly, the signup page for each surveying hike will close 48 hours before each hike. This is to ensure that all registered hikers can receive a pre-hike email confirming the hike, or—in the event of dangerous weather—rescheduling the hike for a future date.

Feel free to share or forward this post to anyone you know who may be interested in attending. It feels pretty great to be kicking off 2025 on such an industrious note, and I’m excited to see many of you out in the field soon—especially at a cold, dark time when the urge to stay home in a pile of fleece blankets can be tough to wrestle with.

There’s more WCT news coming soon, in subsequent newsletters, but here’s one cool tidbit that I’ll share. In the wake of our early November hearing with the Boston City Council and the Wu administration, the City of Boston has started using its channels to promote the WCT. In a recent newsletter offering First Day hike ideas, Parks and Recreation suggested exploring the Walking City Trail, along with classics such as the Black Heritage Trail and the Emerald Necklace linear parks. And if any of you get the neighborhood-centric newsletters from Neighborhood Services, or if you follow your neighorborhood liaison on social media, expect to see WCT rumblings from them too.

Cheers,
Miles Howard

2025 is slated to be the biggest year yet for the Walking City Trail initiative. Between creating new trails and expanding trail events and resources, it will take more than volunteerism alone to make this happen. We’re excited to be in conversation with potential institutional partners, but in the short term, direct grassroots contributions keep the woodstove glowing and make a crucial difference. If you’d like to support the WCT and its upcoming projects, CLICK HERE.