Guides

50 Years of ‘Best of Boston’: Bars

In honor of this year's 50th anniversary of Best of Boston, we're taking a look back. This month, we toast to 50 years of sipping and socializing at Boston’s top watering holes, from dives to super-slick hotel bars.


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1974

Best Bar, Most Pretentious

Jack’s. “The bartenders are Harvard lettermen.”

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1976

Best Piano Bar

Chez Freddy’s. “From seven until two each evening, Beverly Siscoe soothes the world’s wounds with a song.”

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1977

Best Irish Pub

Village Coach House. Boston’s Emerald Isle bona fides are well documented—particularly at the 1977 winner for Best Irish Pub. “The brogues are so thick here you could spread them on toast,” we quipped at the time. “The Irish folk music is loud, the food very good, and the spirits are high (and not in the least dry—you can get tipsy just reading the cocktail menu).”

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1982

Best Bartender, Disco

Richard Boudreau, Metro. His nickname, we explained, was “Bootie,” and he remembered “faces, names, and who likes to talk and who doesn’t.”

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1988

Best Sports Bar

Eliot Lounge. “Where the jocks go to watch jocks.”

1993

Best Real-Life “Cheers” Bar

Rosie’s Bar & Grille. In 1993, the place where everybody knew your name was apparently in…Harvard Square? “Open, welcoming, and serving until the wee hours, it has twice the ambiance and none of the stage lights or lines,” the editors wrote.

Photo courtesy of The Westin Copley Place

2002

Best Hotel Bar

Bar 10. “At lunch and after work, a well-heeled crowd sinks back into high-backed leather chairs and sips extra-strength cosmopolitans,” we noted in 2002 (the height of the Sex and the City craze, naturally). The cosmos may not be as popular an order these days, but this lounge inside the Westin Copley Place is still slinging drinks on the daily—which means it must be doing something right.

2012

Best Bar, South

Union Brewhouse. City folks aren’t the only ones who like to knock one back on the weekends. Down in Weymouth, our tipsy testers loved the “wood paneling, arcade games, [and] collection of retro beer cans” at the Union Brewhouse. “Hopping onto a barstool at the Union Brewhouse is like sneaking down to your uncle’s basement man cave, circa 1976,” the editors wrote in 2012. “Thankfully, the beer selection goes well beyond Bud longnecks.”

Photo by Joe St. Pierre

2022

Best Cocktail Bar

Hecate. In 2022, this sipping spot named for the Greek goddess of sorcery seemingly cast a spell on us: “The rare spirits and ambitious beverages conjured at this chic cocktail den…are like nowhere else in Boston,” we opined. “Then again, neither is the candlelit, cave-like space (max capacity: 24) secreted a stair’s-flight below a dark Back Bay alley. This is high (witch)craft.”

A version of this guide was first published in print edition of the December 2024/ January 2025 issue, with the headline “BoB50: Bars.”