9 Hipster Hangouts in Boston

By Scott Kearnan | November 11, 2013 By Scott Kearnan  |  November 11, 2013

The Boston area is not exactly wanting for hipster magnets. Maybe it's the strong cocktail-geek culture or the young, arts-loving vibe imbued by so many colleges and universities. But some have more to offer than others, so we've narrowed down to some neighborhoods (most in Cambridge and Somerville, natch) and flagship bars and restaurants that are bursting with beards and tattoos - but are worth a visit, whatever your stripe. 

  • Union Square: Backbar

    This cocktail lounge is a sibling to neighboring restaurant Journeyman, a tasting-menu-only restaurant guided by the chef's whim du jour. Backbar is equally ambitious and just as keen on the details - drink geeks rightly swear by its custom pours and hip, clandestine vibe (617-718-0249).

  • Central Square: Brick & Mortar

    Take one part Central Square. Add loyal devotees who have been haunting this spot since it was indie music lounge The Enormous Room. Splash with twenty- and thirtysomething tipplers, their jeans as skinny as the stemware, who have been flocking here ever since it transformed into one of the city's foremost cocktail bars. Result: hipster cred, cubed (617-491-0016).

  • Jamaica Plain: Tres Gatos

    This crunchy 'hood has a gem in Tres Gatos, a cozy tapas hideaway tucked into what looks like a modest Centre Street home. The dining room feels more like a living room, with a comfortable din of plates and glasses (filled with robust wines, of course) clinking. It all leads to a back room that doubles as a record shop and bookstore. That's enough to make any food or music fan purr (617-477-4851).

  • Davis Square: Highland Kitchen

    The Southern-inspired menu - think a "pig-and-pickle" plate and famous fried chicken - lends a bit of a rockabilly edge to this Somerville favorite. A Sunday brunch with live bluegrass music doesn't hurt, and the big canned beer selection only helps (617-625-1131).

  • Inman Square: Trina's Starlite Lounge

    Any place known for crafty comfort food that includes "gourmet" hot dogs is bound to attract a certain irony-loving contingent. Trina's doesn't disappoint, always offering a lively scene of arty young professionals who also appreciate its top-notch cocktails, by legendary local bartender Josh Childs (617-576-0006).

  • Allston: Deep Ellum

    Dive deep into the acclaimed selection of microbrews at this always-hopping hangout in Allston, arguably the epicenter of hipster activity in the Hub. While you're there, gobble gastropub plates that are wonderful by any standard but rank well above what one would expect from the modest price points (617-787-2337).

  • Fenway: Audubon Circle

    Sleek, modern and minimalist, this is the rare alternative to the pub-style watering holes that dominate the Fenway area. Creative cocktails, cold brews and a menu of elevated but not-too-out-there noshes (think potstickers, steak tacos and pressed sandwiches) make it a cool, utterly unpretentious option (617-421-1910).

  • Kendall Square: Friendly Toast

    This place explodes with kitsch. There's the midcentury decor, overflowing with bric-a-brac that looks culled from a yard sale thrown by the B-52's. There's the menu of weird and wacky takes on diner-style fare - breakfast plates and lunch sandwiches that sound slapdash but taste delicious. Wade through the hungover crowds at weekend brunch - it's well worth it (617-621-1200).

  • Harvard Square: Charlie's Kitchen

    Smarter-than-thou Ivy League prepsters rub shoulders with cooler-than-thou hipsters at this late-night, cheap-eats institution that has the vintage feel of a workaday diner out of Grease, as directed by Wes Anderson. The food? Unfussy and utterly satisfying (617-492-9646).

Places Mentioned

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Charlie's Kitchen

Gastropub Cambridge
Food16 Decor14 Service17 Cost$20
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Bar Somerville
Atmo.26 Decor25 Service25 CostI
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The Friendly Toast

American Cambridge
Food22 Decor22 Service19 Cost$20
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Audubon Boston

American Fenway/Kenmore
Food22 Decor20 Service22 Cost$25
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Deep Ellum

American Allston
Food22 Decor20 Service22 Cost$30
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Trina's Starlite Lounge

American Somerville
Food18 Decor16 Service21 Cost$26
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Highland Kitchen

New American Somerville
Food24 Decor18 Service22 Cost$28
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Tres Gatos

Tapas Bar Jamaica Plain
Food24 Decor23 Service23 Cost$37

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