“Being a lobster fisherman runs in your blood,” says captain Fred Penney, hauling a hefty wire cage out of the choppy waters and slamming it on the wooden deck. The trap is wriggling with shiny armoured lobsters and weighs roughly the same as a bag of cement, but 76-year-old Fred, who’s been fishing the ocean around Boston Harbor since childhood, makes the endeavour look effortless.

On a brisk day, he and his crew can lift 400 cages from the sea, but his enthusiasm for the strenuous work hasn’t waned. “My favourite place in the world is to be on this boat, heading out of the harbour into the water at sunrise,” the fifth-generation lobsterman tells me, running a hand over his clipped white beard as seagulls circle in the cobalt-blue sky overhead..

I’ve joined Fred, his son and teenage grandson on their Two Buoys Lobster Tour, a two-hour-long expedition taking visitors from Boston’s Seaport area out into the Atlantic Ocean to haul lobster traps with local Massachusetts fisherfolk. We set off from Boston’s industrial harbour, which jostles with cargo containers and cruise ships, and down anchor four miles adrift of Spectacle Island. As Fred hoists his bounty over the side of the boat with a rope, it becomes clear that modern technology hasn’t quite reached lobster fishing. A string bag stuffed with smoked fish is the bait, the cages are vintage and the fishing method has remained largely unchanged for generations, with the lobsters crawling inside a cage on the sea bed, which is then checked every few days.

Boston’s coastline is prime territory for fishing, Fred tells me. “We have islands that we can hide the boat behind if the weather really starts blowing,” he says as his 45-year-old vessel bobs gently against the tide. The New England lobster that we’re collecting today, scientifically known as Homarus americanus, is renowned for its sweet, succulent meat and sizeable claws. “You only get this kind of lobster along the US east coast,” the waterman says, as he measures the length of a freshly caught animal.

Humble beginnings

Although the lobster roll has clawed its way up the food chain and is today viewed as a luxury item, up there with a decent bottle of Barolo, its origins are far more humble. When Edward Winslow, founder of the Plymouth Colony, set foot in Massachusetts in 1620, he described the abundance of lobsters as infinite. And so it was, that for generations, the lobster was the everyday food of ordinary folk, its meat sandwiched between slices of bread to provide a hearty lunch.

This all changed in the mid-19th century when tourists started to flock to New England, promenading its boardwalks clutching a sandwich purchased from one of the wooden seafood shacks at the shoreline. I’ve come to Boston to continue the tradition they started, and am on a mission to track down the city’s best lobster roll.

Stepping off Fred’s boat onto solid ground, I head over to the North End district, a historic neighbourhood jutting into Boston Harbor. It’s commonly known as Little Italy due to its thriving Italian immigrant community. Amid the narrow side streets fringed with skinny houses, honking mopeds, pizzeria joints and cannoli counters, a queue snakes around the block for a table at Neptune Oyster — a walk-in-only restaurant where diners happily wait for upwards of an hour for a table.

They come to shuck different varieties of ocean-fresh oysters, to slurp bowls of steaming clam chowder and to feast on Neptune Oyster’s legendary lobster rolls. For over 20 years, this seafood institution has served its crustacean sandwich in a handsome dining room with a pressed-tin ceiling and the catch of the day handwritten onto white metro tiles lining the walls.

When I finally make it inside, ceiling fans slicing through the thick summer air, I perch at the marble bar to place my order. A lobster roll is slid invitingly towards me, the bread sporting tiger-stripe griddle marks and the meat daubed with clusters of caviar. Each mouthful delivers warm lobster and salty pearls of exploding caviar on buttery bread. I’m immediately reassured that the long wait for a seat was indeed worthwhile.

We’re on a roll now and, handily, the next stop, Pauli’s sandwich shop, is just a couple of doors away. There to greet me is Nicole Fabiano, office manager and sister of owner Paul Barker, whose family’s culinary ties with Boston’s North End can be traced back four generations. Pauli’s can shift 300 of its standard lobster handhelds on a busy day, but it’s their notorious ‘Lobstitution’ that’s pinned the take-out joint to the culinary map. The monstrously big 28oz lobster roll — its name a riff on the USS Constitution navy warship built in a nearby North End shipyard in 1794 — has found online fame, particularly with food influencers.

As my Lobstitution sandwich is being prepped in the kitchen, Nicole talks me through the process. Supersized rolls are made bespoke by a local bakery due to their extreme length, then piled with the chilled claw and knuckle meat of around six lobsters — “with a very light mayo dressing, which is the traditional New England style of serving,” Nicole says.

The intimidating result is laid before me: a baguette-style roll measuring roughly the length of my arm from wrist to shoulder, heaped with enough lobster to feed an entire crew of sailors. “A few years back, Pauli’s ran a fun promotion where we gave away a free T-shirt if you could finish a Lobstitution in a short amount of time,” Nicole recalls with a laugh. “All these guys turned up to try their luck, but not one of them achieved it.”

I manage to devour around a third of my meal, enjoying the succulent, lightly salted meat cutting through the creamy mayonnaise. But I eventually join the legions of those defeated by the beastly sandwich, leaving satisfied and with a full belly — but sadly no prize-winning T-shirt.

Take the spoils

The following morning, I head to Fenway Park, home to the Boston Red Sox baseball team. It’s game day and coachloads of fans are being dropped off as I arrive at nearby Eventide Fenway, a James Beard Award-winning restaurant. The dining room is drenched in sunlight flooding in through the floor-to-ceiling windows, and illustrations of pincered lobsters hang on the sea-blue walls.

Chef Ezra Gold is busy prepping around 350 lobster rolls to serve that day; in the calm before the storm, he sits down to explain the secrets of the restaurant’s sandwich. “We stick to the core tenants of the perfect lobster roll. It starts with great lobster,” he says. “Next, we add milk solids to our brown butter for a creamy, nutty richness. Then there’s the bun — we use a bao bun, which soaks up all that gooey brown butter.” I hoover up the pocket-sized feast in a few bites, the bun as light as a cloud and the brown butter adding an intense nutty element.

The final port of call is a taxi ride away: Lê Madeline. Situated in Quincy, a diverse suburban city in Greater Boston where 29% of the residents are Asian-American, this Vietnamese restaurant has been causing a splash since chef Peter Nguyen took over in 2024. Raised by a mother who left Vietnam to work as a pastry chef in Boston’s Chinatown, Peter has put his own cross-cultural spin on the traditional lobster roll.

“For my tôm hùm rang me dish, I’ve taken a Vietnamese recipe that normally uses shell-on crab and swapped it with fried lobster,” he says, standing in the marigold-yellow dining room, a mural of fantail fish and lotus flowers stretching along the wall behind him. The meat is dressed with tamarind, topped with roe and put inside an aioli-smeared roll. “What sets it apart from the OG lobster roll is that I’ve added new ingredients to the mix,” Peter explains. I take a bite, relishing the sandwich’s marriage of sweet and savoury. It’s a triumph.

In my quest to find Boston’s perfect lobster roll, I’ve gone big and I’ve gone bougie. But in the new-wave fusion roll at Lê Madeline, I’m satisfied that I’ve found my favourite: a dish that showcases the vibrant multiculturalism of Boston while reeling you in from the first bite.

Three Boston foods to try:

1. Clam Chowder
Try this creamy clam soup at Boston’s Union Oyster House — a favourite chowder spot of Barack Obama.

2. Boston Cream Pie
Don’t be fooled by its pie title: this dessert is actually a sponge cake filled with vanilla pastry cream and finished with chocolate ganache. Try it at Bova’s Bakery on Salem Street.

3. Fried Clams
Deep-fried soft-shell clams are a Boston seafood speciality. Head to Row 34 on the Seaport waterfront to sample them.

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