Boston is a city of contradictions. Home to more higher learning than any other American city, Boston is a college town, but it’s perhaps equally known for its blue-collar culture. You can’t get a medium-regular at Dunkin’ Donuts without bumping into at least one hard-working craftsman whose grandparents arrived by boat for a better life, and whose thick, lazing accent comes to life when it’s time to yell at the Red Sox or Patriots or Celtics or Bruins on TV.
But what’s the one thing that students and townies have in common? They drink. Hence, what was once a city of dive bars and colonial pubs is now a city of dive bars and colonial pubs. Because that’s the other thing about Boston: It don’t eva change. Sure, plenty of beloved bars have closed over the years—we’re talking to you, B-Side—and no one is denying that the craft cocktail culture has made a serious mark upon these cobblestones over the last decade, making it possible to get a delicious and even exciting drink in most neighborhoods. The same can be said of Boston’s wine scene, which is home to one of the country’s most beloved and influential sommeliers—Cat Silirie of the Barbara Lynch Gruppo—but also a crop of younger sommeliers, like Colleen Hein of Eastern Standard and Theresa Paopao of Ribelle, that have helped usher in a new era of wine drinking in the city. In that spirit have come places like Central Bottle and the Wine Bottega, whose tightly curated selections of natural/organic/biodynamic wines would be considered avant-garde in any context. But there’s something about this fair city that’s still a bit averse to change.
Maybe it stems from the pride we take in our early history—we were here first, Virginia, so just deal with it—or the tourists that pile in every summer to visit Paul Revere’s House and The Freedom Trail. It’s not their fault that they tend to drink downtown; someone needs to keep the Cheers bar in business. But while tourists frequent the cheesy Irish pubs of the financial district, and sports fans throw back in the bars around Fenway, and suburban folks—plus clueless students with fake IDs—populate the clubs on Landsdowne Street, the rest of us are drinking in our own neighborhoods. Because that’s perhaps the most important thing about the Boston bar scene—it’s built on regulars.
You’ll find some of the best, unfussy bars that Boston has to offer off the beaten path in Union, Inman and Kendall Squares, in little pockets of Brookline and Jamaica Plain. You’ll find flawless cocktails and local beers, bartenders who’ve amassed a serious following and patrons who share in private jokes. Like any major city, there’s always an element of excitement in trying out the new place, but Boston tends to be more interested in the place that’s been there forever, or at least feels like it has—the old man bars, the dives, the beer bars, the Irish pubs, the places you like to think of as your own little secrets, even when they’re packed. –Jennifer Cacicio