Make for the harbor lights

How to thru-hike Boston's briny "long trail"

There’s a running theory among Bostonians these days that no matter how gentrified and capital-ized our cityscape becomes—in the face of widening inequality—shards of Boston lore will never die. You might be in a Chase Bank kiosk and when you kneel down and peek into the cash dispenser to see why your $20 bills aren’t popping out, you find a BOSTON STRONG sticker slapped on the underbelly of the ATM. A realtor showing you a fancy-pants condo in the Seaport could suddenly take a call on their cell phone and say, in a totally different voice, “Hey, Ma! We still havin’ Santarpio’s tonight?” Or maybe you’re at a cell phone store looking at the latest Apple models. The sales clerk hands you the iPhone 17 and as you fiddle around with its apps, the Dropkick Murphys’ “I’m Shipping Up To Boston” starts blasting from the speaker.

The classic bar-brawler of a song was popularized by Martin Scorsese’s The Departed (which I still argue features one of the more accurate depictions of Boston in a major movie.) At face value, it’s about a sailor who loses his leg while climbing the topsails of some ship that was presumably bound for Boston. It’s a fitting unofficial anthem for the city—because one of Boston’s epic natural features is Boston Harbor itself. At thousands of acres in size, the harbor contains innumerable moored ships, docks, and forested islands with their own beaches and ruins. And if you’ve spent any time gazing into the harbor from Boston, then you’ve probably seen one of these signs posted someplace.

The Boston Harborwalk is a multi-use trail that runs along the jagged shoreline of the Harbor, with its many coves and channels. It was started by the city and a handful of private partners in 1984, as a means of ensuring that large swaths of the waterfront would remain open to pedestrians and cyclists. But what many people don’t realize about the Boston Harborwalk is that it’s 43-miles long. Starting at the Neponset River Reservation in Mattapan, the Harborwalk runs north through the core of Boston before jumping the Mystic River into Eastie and finishing at the west edge of Logan Airport.

I only learned this a couple of months ago. It blew my mind, the sudden realization that Boston has an epic “long trail” with constant ocean views hidden in plain sight. You rarely hear of people completing the entire Harborwalk. I found it baffling that this XL urban trail is so overlooked. And so, for the last few weeks, I’ve undertaken a special project to cap off 2022—thru-hiking the Boston Harborwalk, in segments.