Discover a World of Flavor on the Ultimate Boston Food Trail

Chart a course through Boston's foodie landscape with a seasoned insider.

Boston's Freedom Trail is a globally recognized tourist attraction, but it’s just one among many ways to forge a merry and enlightening path through the city. Black Heritage Trail, Irish Heritage Trail and Women’s Heritage Trail are also well worth the exploration. Not to mention the various docent-guided tours that celebrate Boston’s literary, architectural and cultural heritages.

Woven into this serpentine matrix of pathways is a growing number of guided walking tours for foodies including Bites of Boston—specializing in the South End and Allston; Off the Eaten Path in North End and Boston Foodie Tours which adds Beacon Hill and Back Bay to the mix.

Since the permutations of flavors and routes are practically infinite, here’s our own wide-ranging Where Boston Culinary Trail to get you started. In addition to several well-known eateries—the sorts of places your stomach will complain about if you neglect them—we’ve decided to duck down the occasional lesser-known alleyway so that you’ll not only lick your Boston food chops, you’ll also earn them.

Union Oyster House in Boston

Oysters and Cream Pie 

First, the pillars of excellence: those establishments that skewer familiarity on the rapier of uncontestable awesomeness. At Union Oyster House, the oldest continuously operating restaurant in America, you sit at the very same oyster bar where Daniel Webster once sat and tuck into clam chowder, steamed lobster and gingery Indian pudding—ask for vanilla ice cream on top. A solid stone’s throw away toward the Common, you’ll delight in discovering white-linen wonderland Parker’s Restaurant at the Omni Parker House hotel, where Parker House rolls and Boston cream pie were invented—and are still served.

On the other side of the river, true foodies can visit the Irving Street house where America’s cuisine queen Julia Child lived. Less than five minutes’ walk from there is R.F. O’Sullivan & Son, the beloved Somerville burger bar where the half-pound burgers are “never squished.” You need two hands to hold them.

Frenchie restaurant in Boston

Delights North and South

Over in the South End, the corner of Tremont and Clarendon Streets has been one of the epicenters of Boston dining for decades. Fondly remembered Icarus, Hamersley’s Bistro and Saint Botolph restaurants no longer exist.

Instead, grab a pizza at PICCO—pastry chef Rick Katz’s “pizza and ice cream company”—and onion soup and steak frites at Frenchie, a new, casual wine bar from Loic Le Garrec—of Petit Robert Bistro fame—and sommelier Sandrine Rossi. Addis Red Sea has been serving affordably delectable Ethiopian fare to a diverse, well-traveled clientele since the 1980s. It remains as delicious and friendly as ever.

In the North End, Boston’s Little Italy, Daily Catch dishes up the best, fried calamari, squid ink pasta and calamari meatballs in a room so small you’re essentially eating in the kitchen. Go down the alley next to Bricco and then down the stairs into Bricco Paneterria, maybe the best bread bakery in Boston. At Ristorante Lucia, feast on the Italian-American classics the ‘hood is known for, like chicken Marsala, veal Parmigiano and shrimp Francese. Check out the reproduction of Michelangelo’s Sistine Chapel mural on the second-floor ceiling.

Chinatown in Boston

Macau in Chinatown

Beach Street in Chinatown is so-called because back when it was first settled it really was a beach. Today it’s a warren of shops and Asian eateries, its sidewalks crowded with hawkers selling everything from fresh fruit to knockoff athletic wear. At Pho Hoa, they specialize in Vietnamese noodle soups and rice paper spring rolls. And, down by the Chinatown gate, Great Taste bakery and café makes the city’s best don tot egg custard tarts similar to the Portuguese pastel de nata you’d find in Macau.

Mural at The Middle East Restaurant & Nightclub in Boston

India in Cambridge

A freshening stroll across the Harvard Bridge takes you towards Central Square where India Pavilion, Cambridge’s first Indian restaurant, opened in 1979. Goat vindaloo, shrimp jalfrazee and lamb rogan josh are all worth an omnivore’s attention. Next stop, The Middle East. A legendary restaurant/nightclubs complex where you can enjoy hummus, kebabs and couscous, in addition to cutting edge indie music—recently, Birthing Hips, Truth, Mint Green and Twin Forks.

In nearby Harvard Square, all bon vivants should pay homage at Grendel’s Den, the subterranean restaurant and bar that won a landmark 1982 Supreme Court case that allowed them to sell alcohol within 500 feet of a church, a legal challenge to blue laws in nine states. Grendel’s’ vegetarian and vegan friendly menu of soups, salads and comfort fare is half price between 5 pm and 7:30 pm nightly.

StreetFood Revolution in Boston

Street and Store

No Where Boston Culinary Trail excursion would be complete without a walkabout of Allston with its student residents and many inexpensive, international restaurants. At StreetFood Revolution, the young owners are committed to uncompromisingly authentic Chinese street food including mega-hot mala soups you can individualize with chicken gizzards, tripe, tofu skin and enoki mushrooms. You should also visit Berezka International Food Store—a Slavic eats emporium—to stock up on pickles, smoked meats and the cheapest caviar in town for the ride home.

Other locals may tell you we missed a spot or two, but no Boston foodie trail can ever be truly definitive—there’s always something new to discover just around the next corner. With apologies to Ralph Waldo Emerson: “Do not go where the path may lead, go instead where there is no path and leave a trail ... of crumbs.”