Boston’s historic Seaport is reborn as the city’s newest attraction

Waterfronts have long witnessed the birth of American cities. For Old World hope-seekers, they were the first vision of a new life over the horizon – later docked gargantuan carriers transferring the steel and concrete that would construct the American Dream. They have sheltered the misplaced, or even hid queer communities in search of intimacy. From Philadelphia’s Penn’s Landing to New York City’s High Line, waterfronts have been both the windows and basements of industrialisation, disguised in silhouettes between towering skyscrapers they helped erect. 

In just over a decade, changes in city waterfronts have skyrocketed, adding vacant parking lots, crumbling railways, and abandoned warehouses into the cities’ established urban textures. I took my boyfriend and dog, Bagel, for a weekend getaway from New York to Boston – from one of the first American cities to rise through its waterfront to the other – to discover how this New England metropolis transformed its seaport into a sleek destination.   

Autumn’s orange and red foliage may not have appeared yet, but September is always generous with remnants of an August sun. After leaving behind a summer strictly dependent on rosé-centric, socially distanced picnics, an impromptu weekend away to Boston on the season’s tail end is our sweet escape, one crowned with vistas of postcard-charming Connecticut and Massachusetts towns along the way.

Through the Central Artery of Interstate-93, we enter the Seaport, nestled between the city’s historic North End and South Boston, characterised by green-lit shamrock pub signs and tightly lined colourful townhouses. The atmosphere suddenly lends itself to a contemporary social and residential hub, bordering the old city’s signature landmarks, Boston Common or Newbury Street. The district is a starchitects’ hall of fame, with buildings designed by Rem Koolhaas’ OMA, Morris Adjmi, James Corner Field Operations or NADAAA, which ‘embody elegance, soul, and character that will stand the test of time,’ says Yanni Tsipis, the head of Seaport’s development firm, WS Development.    

Since opening in 2015, The Envoy Hotel has been an emblem of the area’s transformation with its fore-fronting location by Seaport Boulevard and panoramic rooftop bar, Lookout. The glass-clad hotel sits by the Fort Point Channel, which separates the old town and the high rises with a five-minute bridge walk. Sipping a cocktail on its rooftop or waking up in one of its rooms, one witnesses the rustic blend with the glossy here. For an early bird like myself, this was seeing a truck driver transport cases of rolls to the lobster shack under our window, while seagulls lingered over the channel. 

My morning walk to Tatte Bakery & Café for its widely recommended shakshuka is gently interrupted by early runners near the harbour. After dipping our pillowy challah slices into spicy tomato sauce, I notice the San Francisco-based retailer Everlane, which has recently built a cult following with its clean-cut aesthetic and sustainable design. After once convincing me to wait in line to enter its Soho store, my boyfriend doesn’t have to make much effort to have us walk in for a pair of denims. The next temptation lures us for a dip at the nearby Carson Beach, in Boston’s hilly south side. In less than a 10-minute drive from our hotel, we are on a beach tucked in the city centre. ‘Are we in Miami?’ we ask ourselves, but a six-pack of Vermont’s seasonal sour Hermit Thrush reminds us we are in New England, and there are gorgeous beaches here, too.

The approaching Sunday dusk is perfect for ‘seeing’ Nancy Baker Cahill’s augmented reality public art piece, ‘Liberty Bell’. I pass through Maryanna McDonald’s portrait of a woman – à la Kate Hudson in Almost Famous – onto repurposed VHS tapes hung in The Envoy’s lobby. I then head to the Congress Street Bridge to catch Cahill’s energetic drawing of an abstract bell on my phone. Hovering over the bridge, the cloud-like animation chimes on my AirPods. The bell’s digital toll joins the honks coming from the boats swaying underneath the Northern Avenue Bridge. Art, in fact, adorns the whole district, which roughly spreads across 20 blocks. 

We walk down the Seaport Boulevard in search of Okuda San Miguel’s seven larger-than-life geometric sculptures, including that of a gigantic squirrel and water eruption. The Spanish artist named the series Air Sea Land after three main elements he thinks permeates the Seaport. On Fan Pier Boulevard, look up above Italian restaurant Tuscan Kitchen to catch Frank Stella’s bright mural, Damascus Gate (Stretch Variation I), the abstract art pioneer’s colour-bursting interpretation of architectural precision and public intervention. Contemporary art museum ICA Boston was among the first to position itself in the district in 2006 with a Diller Scofidio + Renfro-designed building on the Harborwalk. Inside, Nina Chanel Abney’s wall-spanning mural about police brutality greets us, followed by compact but piercing solo exhibitions by Sterling Ruby, Tschabalala Self, and Carolina Caycedo. 

Back in Tuscan Kitchen, we perch by the window for an Italian feast, interpreted in New England-style seafood. We are in the nation’s lobster capital. A mountainous, three-tier seafood platter lands on our table, with oysters and raw scallops crowning a bed of ice on its lower level. The second tier hosts clams over its sea of ice, as well as meaty lobster tails and jumbo shrimps. This is the Kilimanjaro of seafood platters and my boyfriend and I are two hungry climbers braving the ice-coated rocks – or, in our case, shells. 

After dinner, we take a stroll to North End for an Espresso Martini at Bricco after a recommendation from our bartender at Lookout. The Seaport’s silhouette from this side of the channel resembles a wave of lights, plunged into a nocturnal briskness, different from its daytime bustle with pedestrians across it harbour walk and boats cruising the water. That is exactly the panorama that sends us away the next morning as we drive home, first with stop-offs at the witches’ town Salem and the wavy fishing peninsula, Marblehead.