Upcoming Events: Boston Summer Sunset Walks

Let's explore the City On The Hills Trail together

6/10/25 Update: All of the remaining summer sunset walks have been cancelled due to a sports injury incurred by Miles Howard. These hikes will be rescheduled in August for late summer.

Boston. It has been a fantastic launch week for the City On The Hills Trail. We’ve just gotten reports from people who have explored sections of the trail and we’ve garnered some press coverage from Universal Hub, WBUR, and WBZ News radio. Now it’s time for the essential second step after launching a trail. Walking the whole trail as a group.

So without further ado, I’d like to introduce a new, upcoming series of group walks on Boston’s City On The Hills Trail—the inaugural edition of Summer Sunset Walks.

As some of you will recall from participating, I’ve usually led guided walks on Boston’s Walking City Trails on weekend mornings. And the recent surveying walks along the City On The Hills Trail were no different. Except for the last one. Due to conflicting weekend events and curiosity, I decided to shake things up for the fifth surveying walk by having our group meet at 2:00pm. This allowed us to spend the majority of our time ambling through the softer light of the mid-to-late afternoon. By the time we reached the arcing causeway to Castle Island, a Boston harbor sunset was underway. It was a gorgeous way to conclude the adventure, and it left me curious about trying it again.

So this late spring and early summer, that’s what we’ll be doing! These upcoming five section walks along the City On The Hills Trail will kick off in the mid-afternoon and wrap up during the magic hour. While this will mean starting the walk during a hotter time of the day (if the summer temperatures get here early) it will also mean cooling conditions as we walk. And again, is there anything more romantic than finishing a foot journey with new comrades against the backdrop of a sunset? I don’t think so.

As before with the surveying walks, registration for these Summer Sunset Walks will open two weeks before each event and you’ll hear about it via this newsletter and the Walking City Trails Instagram page. Each signup window will close 48 hours before each walk, so that nobody misses any email updates sent shortly before the walk (like a date change due to dangerous weather, which can happen as things get hotter.) But the timing of these walks isn’t the only thing that I’m changing up this time around.

In prior summers, I’ve hosted the registration materials for Walking City Trails group walks on Eventbrite, with a finite number of “tickets” available for each walk—half of them being free, and the other half being $20 apiece. But this summer and beyond, I’m doing away with that model. The signup page for each Summer Sunset Walks will be a Google Form containing all of the requisite details about each group walk. There will not be a signup limit. And there will be no cost to register for any of the group walks.

My rationale behind these changes really comes down to two things. Accessibility and vibes. In practice, I have found that when financial barriers are removed from walks, it not only draws a wider range of walkers, but it also makes the atmosphere of the walk feel even more rambunctious and gregarious. From a hosting perspective, at least. So that’s why the Summer Sunset Walks will be free and capless. I’m excited to see what happens if we draw a Spartacus-sized group of walkers, just as much as I will value the intimacy of a smaller group. And the wonderful and generous community support that many of you have contributed to the Walking City Trails initiative over these last few weeks has offered relief from the pressure to generate new revenue to fuel the project.

See you out there real soon!
Miles