I first set out to eat a lobster roll. I am in chilly Boston, perfect weather for the city’s other favourite food icon: clam chowder. On my obligatory visit to Harvard University, I rub the John Harvard statue boot for good luck and then set out on my mission.
I am rewarded almost immediately at Harvest, a cosy restaurant at Harvard square which celebrates New England farmers and purveyors. The space is cosy and deliberately old school, serving up bowls of comforting New England Clam chowder rich with potatoes, bacon and cream, all woven together with the freshness of leeks and celery.
Boston is hosting seven matches for the FIFA World Cup 2026, including one of the quarter-finals. The games are being played at Boston Stadium, historically known as Gillette Stadium. According to the stadium website, fans will be able to buy fried chicken sandwiches, hot dogs, soft pretzels and even salads, fruit cups and veggies plates at their concession stands. However, for a proper taste of Boston, here is our guide.
Starting with my lobster roll.
Legal Sea Foods
Legal Sea Food’s flagship Harborside restaurant overlooks Boston’s waterfront
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We watch seagulls wrestling the wind from the large French windows at Legal Sea Food’s flagship Harborside restaurant, which overlooks the city’s scenic waterfront. As we enter the huge, sunlit space I am distracted by the expansive oyster bar, and we order a plate. They are briny, cool and satisfying, served on ice with a fat lemon wedge.
Beside clam chowder, the menu boasts lobster bisque, mussels served with garlic-butter broth, and New England clams (described as “sweet and petite”). I am on a mission though, and I focus on the rolls. Boston traditionally offers them in two ways. You can order them Maine style, where the meat is chilled and served with mayonnaise.
Buttery lobster rolls at Legal Sea Foods
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Huge Galdones
I am not strong enough to resist a warm buttered roll, however, so I order the Connecticut version, where generous chunks of lobster glossy with butter are served on a just-toasted roll. The locally sourced lobster is excellent, and the hearty dish is intelligently built to let each flavour shine.
The Union Oyster House
A vintage photo of the Union Oyster House, the oldest continually-operating restaurant and oyster bar in the United States
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We regally settle at the Kennedy Booth with oversized prawn cocktails. Designated a National Historic Landmark, The Union Oyster House is the oldest continually-operating restaurant and oyster bar in the United States. Housed in a Pre-Revolutionary building, it started serving food in 1826, then launched its iconic semi-circular Oyster Bar in 1897 serving ‘bench opened’ oysters, freshly shucked for diners.
American presidents, including Franklin Roosevelt, John F Kennedy and Bill Clinton, have dined here. Kennedy, who visited the Oyster House every Sunday at noon when he was in Boston, sat at number 18, the booth I am seated at.
Oyster’s house crowning gem, freshly shucked oysters for diners
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We order cups of steaming clam chowder (of course) served with fluffy, crumbly cornbread, still fragrant from the oven. Then, following in JFK’s footsteps, get a round of classic Daiquiris. John Paul, the manager who tells us how he worked his way up from a bus boy at the restaurant over 11 years, also introduces us to Sam Adams Colonial ale, specially curated for Oyster House. Our prawn cocktail is simple but dramatic, starring huge, juicy prawns posed beside crisp lettuce. We soak in the atmosphere as we eat: polished floors, wood-panelled walls and a large stuffed lobster, weighing 44 pounds.
“The restaurant is a living museum,” says John, saying they have a capacity of 500 diners at a time, and are always packed. Their cornbread, made fresh every day, is everyone’s favourite order and he says, “We go through hundreds and hundreds of pounds of it every day,” adding with a laugh, “I gained about 20 pounds when I started working here.”
On the menu at the Michelin-honoured Mooncusser, helmed by Chef Carl Dooley
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An insider’s guide to Boston: Chef Carl Dooley, Mooncusser
What’s your go-to Boston comfort food — and where’s the best place to get it?
Singh’s Roti Shop in Dorchester – it’s an amazing spot for Trinidad carry-out. They have the best goat curry and the Doubles are awesome. It all is super delicious and a great representative for the Caribbean population here in Boston.
What’s one thing first-time visitors usually get wrong about the city?
Maybe vistors come here for history, but then hopefully they realise the innovation, the arts, and definitely the food scene while here.
Is there a local ingredient you wish more people paid attention to?
Pupusas! We have a large Salvadorian population here in the city – and La Reina in East Boston is amazing. I always recommend to my friends and guests that they should go visit East Boston, try some of the delicious Pupusas at La Reina, and then walk the harbourfront. These are just super authentic and delicious. It’s amazing what is going on in East Boston with the community and the food scene – and those views are unbelievable.
What is one under rated Boston experience visitors should not miss?
I recommend to friends and visitors alike – go rent a Blue Bike and ride along the Charles River. Go from Esplanade and Back Bay over to the Mass. Ave Bridge and head into Cambridge for lunch at Central Square. It’s really the best way to experience the city.
Which neighborhood do tourists tend to overlook but really should spend more time at?
Allston. Allston has great dive bars, awesome Korean BBQ, and some super small independent music places. Catch a show at the Brighton Music Hall – it always has great shows. The neighborhood has a bit of a Brooklyn vibe which is cool.
Chef Carl Dooley is recognised nationally for his creative take on fresh seasonal New England ingredients viewed through a global lens. Michelin has listed Mooncusser as one of its recommended restaurants, and Dooley is a multiple James Beard Foundation nominee, a Top Chef Top Five Finalist, and Eater Boston Chef of the Year.
Contessa
The banquettes are pink, the roses are fresh and even the elegantly-dressed diners seem like they were especially cast for the scene. Contessa has the charm of a Wes Anderson film: every angle promises romance. As I weave past busy tables, cheery with sunshine and conversation, I admire sweeping views of Back Bay and the Boston Public Garden from the rooftop trattoria.
Diners can enjoy a view of the sweeping Boston skyline at Contessa
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This is reportedly one of Boston’s toughest reservations to snag, and for good reason. Perched atop the Newbury hotel, Contessa offers Art Deco references, mid-century modern detailing and an addictive spicy lobster Capellini.
Noticing practically every table ordering bowls of the Maine lobster tangled in delicate angel hair pasta, and a decadent sauce of tomato, cream and Calabrian chilli, we follow suit. Secondi also involves a hearty Macaroni with Wild Boar Ragu topped with pleasingly salty pecorino. Since it is Sunday brunch, we also order Florentine Benedicts topped with curls of prosciutto, hollandaise, spinach and perfectly poached eggs.
Although Contessa boasts signature Italian and French wines, from Piedmont, Tuscany, Bordeaux, and Burgundy, I cannot resist the call of their chilled Martinis. They do three, and do them well: A Vesper, with gin, vodka and cocchi americano. The Classic, with gin, vermouth and bitters, and a deliciously dirty version with olive brine.
Dessert is fluffy Panettone French Toast, and I sink back into a couch as comfortable as a hug. Football fans will find plenty of excitement inside the stadium. I hope they also discover the pleasure of a generously buttered lobster roll, oysters on ice, and the stories that shaped America’s Cradle of Liberty.
The writer was in Boston, on invitation from Brand USA
