The simple, straightforward style of cooking that the pilgrims brought with them has long been replaced by an eclectic dining scene filled with global influences and flavors that represent the city's diverse population.
That doesn't mean you shouldn't sample tried-and-true Yankee classics. Illustrious locals with surnames like Kennedy still flock to Union Oyster House on the Freedom Trail near Faneuil Hall. The menu, largely unchanged for two centuries, features fresh Atlantic seafood such as briny oysters, New England clam chowder, and broiled scrod served with vintage sides like baked beans and cornbread. Colonial-style desserts include home-baked gingerbread and warm Indian pudding topped with soft peaks of whipped cream.
Italians have been immigrating to Boston for generations, and the North End is the city's Little Italy. At Bricco, the smell of olive oil, barrel-aged vinegar, and prosciutto transports you to the old country without a passport. Order light-as-a-feather pasta, creamy risotto, or the tomato-based fish soup brodetto, which is teeming with lobster. The menu also features Wellfleet clams, mussels, calamari, shrimp, and monkfish.
For dessert, the cannoli rivalry between Mike's Pastry and Modern Pastry, both on Hanover Street, is as real as New Haven's pizza rivalry. Try them both and decide for yourself.
Lucy Ethiopian is an unassuming place on Massachusetts Avenue. If you're not familiar with this flavorful cuisine, this is the place to explore the seasoned meat, legume, and vegetable stews that you scoop up with injera, a spongy flatbread made with fermented teff flour. There are numerous vegetarian and vegan dishes.
At Anoush'ella in the South End, the owners serve mouthwatering Eastern Mediterranean food that harkens back to the Armenian and Lebanese street foods of their childhoods. Flaky hand-rolled flatbreads are wrapped around fresh ingredients such as hummus, baba ghanoush, spiced minced lamb, and lentils. Soups, salads, and grains are healthy, inexpensive, and delicious. They have an additional outpost at the Time Out Market near Fenway.
Roxbury is a residential neighborhood with a strong sense of community pride. Dudley Cafe embodies this identity. It's a casual eatery that partners with nearby high schools, training students and creating job opportunities for them. Mingle with regulars, dine on wholesome food, and listen to live music performed by local talent.
When it's time for an alcoholic beverage, Boston has plenty of tricks up its sleeve. Shore Leave in the South End serves retro-style tropical cocktails, like a Blue Hawaii, in a whimsical setting. Burgers, wings, tater tots, and hot dogs are the perfect accompaniments.
Craft-beer lovers have a lot of choices, but hopheads shouldn't miss the taps at Trillium Brewing, where the double-dry hopped varieties have a loyal fan base. They have several locations, including Fort Point in the Seaport District and a beer garden at the Rose Kennedy Greenway.