Beantown. The Hub. Birthplace of Democracy. City on a Hill.
The list of monikers for one of the oldest cities in America is long and varied—nearly as much so as its drinking culture and watering holes.
Boston’s bar scene is about much more than alcohol. These are spaces and places for people to come together, to form community, to share ideas…and a drink. Here’s a tour of some of my favorite spots.
Boston’s Downtown Crossing district runs adjacent to the east side of the Boston Common and is crawling with historical landmarks. The bars here, too, carry their own history. Head first to Silvertone Bar & Grill, a basement bar with divey looks that conceal some of the area’s best bar food and damn good drinks.
A few blocks away is JM Curley, named for Boston’s most notorious mayor, James Michael Curley. In thick with the mob and shameless about his Irish and working class roots, Curley’s flouting of Brahmin (upper-class Protestant) standards is what put a cap on the number of liquor licenses allowed within the city at the repeal of Prohibition in 1933. Continuing Curley’s legacy, JM is a no frills, no bulls**t bar with a carefully crafted cocktail menu.Just down the street you’ll find The Tam, a cash-only dive bar that opened some time in the 1940s and has, blissfully, changed very little. I wouldn’t try to get a cocktail, but if you want to see shot- and beer-slinging at its finest, be sure to stop in.
The South End
From Downtown Crossing you can walk to the South End. Bar Mezzana on Harrison Avenue is the perfect bar for just about anything. With a well-crafted spirits list and cocktail menu and a staff of highly knowledgeable bartenders, you won’t go unimpressed—or thirsty. My favorite feature, though, is the wine list. Instead of sauvignon blanc or cabernet sauvignon, you’ll find wines “to the tune of sauvignon blanc” and “reminiscent of cabernet.” It’s a great place to find a new wine to love.
Right across the street is its sister, Shore Leave, a tiki bar and restaurant you truly shouldn’t miss. Its cocktails and rum list pay homage to the craft and history of the spirit and the centuries-old relationship rum has with New England.Around the corner from Bar Mezzana is Lion’s Tail, a darkly wooded, sexy haunt named after the classic cocktail. The cocktail menu is four pages long and so much fun to read that, even if you know you’re going to get a High Life, you should look through it.
A few blocks away you’ll cross into the old South End, where bars are much older, smaller, and well-worn (all of which are compliments). The Franklin Café, for example, has six or seven tables and a 12-seat bar. You’ll get the feeling everyone there knows each other—and a lot of the time, they do. Open until 2 a.m. and serving food until 1:30, this is a late night go-to for area restaurant staff.Across the street from the Franklin is Coppa Enoteca, Boston’s premier spot for Italian small plates. Always busy but always worth the wait, try of one the house-blended spritzes on draft and drool over the charcuterie (prepared behind the bar) while you wait for a seat to free up.
The North End
Don’t drive to or in the North End (aka Boston’s “Little Italy”); the neighborhood’s tiny streets are constantly crowded with canoli-seeking-pedestrians and the occasional double parked Escalade. Hanover, the main street of the North End’s commercial area, is lined by seemingly nothing but bars and restaurants, but two you shouldn’t miss are Parla and Cafe Vittoria.Like so many good things, Parla is direct and authentic about what it does and has a stellar sense of humor. Fashioned as a speakeasy with a major nod to Boston’s bootlegging history, its menu reads like a graphic novel and begs to be photographed. It’d be tough to go wrong with any of the drinks, but if you can’t decide, The Dungeon Master is a 10-drink list, one for each face of a 10-sided die. Roll away and see what comes up. No givebacks or second rolls.
Caffe Vittoria opened in 1929 and, something tells me, not even Prohibition shut it down. Largely a coffee shop (but with a liquor license) this is the perfect place for an espresso and a shot of amaro, amaretto, or Bailey’s.
You should get to Southie, Boston’s traditional Irish immigrant and Irish-American neighborhood, before it’s entirely transformed into South Boston by the influx of luxury condos and ever-increasing rents.
Croke Park or, as locals affectionately call it, Whitey’s (yes, for Whitey Bulger), is home to some of the best free pool tables in the city. Cash only, no sign aside from the black roof, and full of a tightly knit group of regulars; outsiders are welcome as long as they play by the rules: Don’t be a jerk. Or, if you’re gonna be a jerk, know someone’s gonna get on you about it. If you start to understand the thick Irish brogue on most of the bartenders, it’s probably time to call it a night.
Down the street from Croke Park and directly across from the Broadway T stop, Moonshine 152 comfortably straddles the line between old and new South Boston with affordable drinks, a cocktail-oriented bar staff, and some of the best food around.
If you like tequila and tacos, and don’t mind a bit of a hike, go to Yellow Door Taqueria in Dorchester. Seriously, just get there.
Fenway/Kenmore SquareAcross town from Southie lies Fenway Park and the Kenmore Square area. The streets directly surrounding Fenway are packed with bars, and every single one of them is a sports bar on game day. A bit further afield lie Eastern Standard and The Hawthorne, both bars of the Commonwealth Hotel and nationally renowned for their cocktail programs. The menus change frequently and often focus on classic drinks as well as featured house cocktails.
With more than 150 whiskeys and one of the best oyster shuckers in the city, Citizen Public House is a go-to before or after a Sox game. Try one of the signature flights to taste three whiskeys you may not find anywhere else. Across the street and to the left is Tiger Mama, the tiki-inspired outpost from Chef Tiffani Faison. With a stunning collection of rums and a house cocktail menu that will make your mouth water, Tiger Mama goes one step further with a collection of tiki mugs so inspiring you’ll need to put down a glassware deposit before you’re left alone with one.
Cambridge and Somerville
A trip to Boston without visiting Cambridge and Somerville, the somewhat smaller towns across the Charles River, would be a tragedy. While perhaps best known as home to MIT, Harvard, and Tufts University, Cambridge and Somerville also house an eclectic and spirited collection of bars.Kendall Square (Cambridge)
Hit State Park for pool, board games, shuffleboard, and pitchers of your favorite highballs, like Pimm’s Cup and Tom Collins. Right upstairs is Mamaleh’s, a traditional Jewish deli with a full-blown, old timey soda fountain bar—and a full liquor license. Try the house-infused aquavit and literally anything on the food menu. But go early: Mamaleh’s is open 7 a.m.-4 p.m. weekdays and 8 a.m.-4 p.m. on weekends.
Central Square (Cambridge)
Central Square bar life is centered on Massachusetts Avenue, which means you can stroll up and down for hours. Places not to miss are A4Cade, a giant arcade with a full bar. Grab a bottled spritz and a handful of tokens and see how far you get on one of the dozens of pinball machines, or partner up with friends for race car driving, hunting games, and free toss races. If you’re looking for something quieter but still exciting, Green Street is a cozy cocktail bar and home to the city’s longest standing liquor license.
You’ll be hard pressed to get through Harvard Square without stopping into one of the Grafton Group’s various hubs: Grafton Street Pub, Russell House Tavern, PARK, The Hourly, and Temple Bar are all well-to-do spots with well-crafted drinks and a broad selection of local (or local-ish) beers. If there’s one place I always want to hit in the Square, however, it’s The Sinclair, a bar/restaurant/music venue bringing in a diverse crowd for both drinks and live bands.
Davis Square (Somerville)
There are two places you should never miss when in Somerville, and they’re about a five-minute walk from each other. Start at Saloon, a whiskey-heavy basement speakeasy, for a beautifully crafted cocktail, and check the calendar for its next Supper Club (a night of food, drink, and burlesque). After Saloon, go up the street to 80Pub, every Camberville resident’s favorite dive bar. Cash only. Heavy pours. Many red Solo cups.
Inman Square (Somerville)
Trina’s Starlite Lounge is a home away from home for everyone who comes in. A powerful stronghold in the local restaurant industry, Trina’s is best known for Industry Brunch, a mimosa and Fernet heavy brunch/dance party held every Monday.