Being a food writer and a local walks/hikes leader for the Appalachian Mountain Club, I have been to nearly every nook and cranny in the Greater Boston area, but both of my alter egos have mostly kept me away from the Seaport District of Boston.
Well, the changing of this waterfront area (which is technically part of South Boston) from a dusty, sketchy “wild west” section of town to a swanky and chic playground for the rich is so jarring that it feels almost more intimidating now then it did before.
Behind the glitter and trendiness, however, are pockets of the old waterfront along with fairly extensive green areas (or blue if you’re a boater), and with this knowledge I led an AMC walk a couple of years ago to try to get a taste of the more tranquil side of the Seaport, sadly with some not-so-great results due to half-finished walkways, heavily-trafficked roads, shuttered independent restaurants, and more than a few drunk people encountered along the way.
We decided to walk back into the belly of the beast once again on a recent AMC walk, this time with a specific plan that included visits to newly-added open spaces and walkways, both of which kept us mostly away from the neighborhood hubbub.
The results? An enjoyable and dare I say it, memorable evening in a part of the city that many tend to ignore.
Our walk began at South Station, which is a good starting point for several sections of Boston, including the Fort Point neighborhood, which we strolled through at the start—and the end—of the journey. Taking the Harborwalk along the east side of Fort Point Channel from Summer Street, we headed north, gawking at the spectacular views of the Boston skyline across the water while also viewing the wonderful old warehouse and loft buildings to the right. It is difficult to pinpoint exactly where Fort Point ends and the Seaport District begins (these days, the marketers claim that everything north of Stoughton is the Seaport District), but as we walked under Seaport Boulevard, the peace and quiet started to be replaced by loud voices and clinking glasses while the historic buildings quickly gave way to huge glass towers, cranes, and scaffolding everywhere. We knew we had arrived.
When you get to the Seaport Boulevard bridge over Fort Point Channel (also known as the Moakley Bridge), the obvious route to many would appear to be Seaport Boulevard and east into the heart of the district, but for our purposes—basically, to stay away from the heart of the Seaport—we continued north on the Harborwalk past the long-closed Northern Avenue Bridge, lamenting for a few minutes how the structure is now off-limits to pedestrians, before winding our way past the Moakley Courthouse with the mouth of Fort Point Channel to our left.
It was around this point that the noise and traffic quickly started to vanish again, with unforgettable views of Boston Harbor emerging. We quickly found ourselves at Fan Pier Park, a gorgeous oasis right on the water with views of downtown as well as East Boston and Charlestown. Then the Harborwalk continued to turn a bit and hug the water, going past a still-in-the-works pavilion that will feature a cafe from the Frank Anthony’s Gourmet Market folks under its stairs.
This part of the walk by Fan Pier appeared much different from two years ago, and we felt thrown off in a number of ways. (Waterside Avenue? What the hell is Waterside Avenue? What’s the purpose of this pavilion that is basically a staircase to nowhere? Why do the roads have patterns that look like dress socks?) The peace and quiet was particularly nice though, and just where the Harborwalk veers right at the pavilion, a long dock appears out of nowhere that can be accessed by the public (well, we didn’t see any signs saying otherwise, at least).
Walking down to the dock brought us to extraordinary views of the harbor and the islands, and since it was around 7:30 pm, a sunset over the water that made our knees weak. As we stood mesmerized by it all, a water taxi pulled up and let out some people who appeared to be in desperate need of booze (I nodded in sympathy), and we noted that this would be a fun way to bounce around Eastie, Charlestown, the North End, and downtown. Or even better, a way to find places to drink booze.
Standing at this beautiful little piece of the waterfront, we had a feeling that it couldn’t get much better, and it turns out we were right, at least not counting a hidden section of Fort Point (more on this in a bit). Turning south away from the harbor and toward Northern Avenue, the Harborwalk seemed to peter out with construction taking place in a number of areas, though this part of the walk is in much better shape than it had been two years earlier.
We took a left toward the Institute of Contemporary Art, with water views still at our left, and we walked the perimeter of the outside of the ICA, noting the sheltered outdoor space that would seem to be a nice spot for concerts and other events, then we wandered along the water to what turned out to be a real head-scratcher. Right there, within sight of all the uber-high end residential towers and upscale restaurants is a … a fish cleaning station? And a vending machine that sells bait?
We tried to picture multi-millionaires walking over in loafers to grab a pint of frozen squid while bringing over a five-pound flounder to prepare for dinner, and, well, we just couldn’t. Could it be that the Seaport District isn’t all about money and glitz after all?
Our next stop, after a miserable walk past the long-closed Eastern Pier II restaurant and down Seaport Boulevard for a block or two because there was really nowhere else to walk, brought us to the historic Boston Fish Pier, which confirmed to us that there is more to this area than gorgeous views and multi-million dollar condos.
As pretty as the green spaces of Fan Pier are, the Boston Fish Pier is, to put it mildly, butt-ugly, with a desolate strip of road leading to a gate. Beyond that are grim-looking utilitarian buildings on both sides where fish wholesalers can be found, along with a little-known breakfast and lunch place called Trio Cafe and the legendary No Name Restaurant.
This latter spot represents everything that the new Boston waterfront is not, as it is a century-old haunt that caters to families and tourists alike, along with those who aren’t really into the hotspots nearby. It’s not the best seafood restaurant in town, but it is one of the last vestiges of “old” Boston around here, especially with places like Jimmy’s Harborside and Anthony’s Pier 4 no longer up and running.
As tempting as it was to dine at the No Name for the sake of old times, we had another throwback spot in mind, and after returning to Seaport Boulevard and walking the scenic dock behind such places as Tony C’s, Del Frisco’s, Temazcal, and Legal Harborside, we left the water for the time being and crossed the street to J. Pace & Son, where we ordered sandwiches at the counter, grabbed some chips, cookies, and drinks, and sat in their plain little dining area off to the side, a world away from the traffic and hordes of people just outside the door, and also a world away from the prices at some of the eateries in the area (most of us paid about $10 for our dinners).
At this point of the walk two years ago, things started to go downhill in a hurry because we made the mistake of taking Seaport Boulevard back toward Fort Point, where we encountered loud, staggering groups, people literally talking about stocks on their phones (pro tip—we don’t care about your investments), and tourists who seemed hopelessly lost with one even asking where Faneuil Hall was. Having learned from our mistakes, this time we followed a mix of Park Lane and little green spaces behind Seaport Boulevard, passing by another cheap eats spot called Larry J’s BBQ Cafe as we made our way to the Seaport Boston Hotel, where we warmed up next to the fireplace (much to the chagrin of the woman sitting there, as there were 10 of us), then took a peek at the attractive Tamo Bistro + Bar before continuing through the building and exiting it near B street.
From there we crossed over to Northern Avenue then turned toward Fort Point at Gather (a restaurant and bar that feels like one of the few true community-minded spots in the neighborhood), going past the beautiful Massachusetts Fallen Heroes Memorial in Seaport Square Park. From there, we crossed Seaport Boulevard one more time and returned to Fort Point.
I’d be remiss to leave out our walk through the Fort Point neighborhood, because it really is one of Boston’s true gems. Within a minute or two of leaving the Seaport District, we were in an area of narrow lanes, big old industrial buildings, and absolute serenity with the sounds of traffic cut off and not a person to be found other than a guy carrying beer who wasn’t kind enough to offer us any.
Our route took us down a small piece of the quaint and charming Farnsworth Street, then over to A Street and Necco Street, where we raised an imaginary glass to the Channel, a legendary music club that remains sorely missed more than 16 years after its closing. From there, we wandered through the rather funky and artsy Channel Center area before taking a right on W 2nd Street to Dorchester Avenue, veering right again on another piece of the Harborwalk by a security gate and coming to what’s basically the start of Fort Point Channel. This part of the channel is, to put it simply, absolutely amazing, and if you’re a photographer, it is one of the best places to find views of the skyline. The Harborwalk continues north here for quite a distance (with endless views of the water and the city along the way) before ducking under a building, going up a staircase, and returning to the starting point on Summer Street.
So, is the Seaport District a pedestrian-friendly area with lots of independent restaurants and a real sense of community? Not really, but it isn’t the monster that some people think it is either, and if you do it right, you can actually spend quite an enjoyable afternoon or evening wandering the entire area. (And don’t forget to bring your bucket of fish to clean if you’re so inclined.)
Marc is the founder of @hiddenboston, a textbook editor, a hike leader for @AppMtnClub, and a food and travel writer and commenter for DigBoston, NBC/NECN, WBZ, WMFO and indie617.