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 recently hosted seven matches for the FIFA World Cup 2026, including one of the quarter-finals. The games were played at Boston Stadium, historically known as Gillette Stadium. But beyond the stadium lies another reason to visit. Guided by locals, I set out to discover the city’s food scene.

Starting with my lobster roll.

Legal Sea Foods

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.

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 

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.

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.”

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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.

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. The crowds that came for the FIFA World Cup may have gone home, but Boston Stadium will continue to draw visitors. 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

Published - July 09, 2026 02:32 pm IST