Where to Drink Like a Local in South Boston

Back when Irish gangster Whitey Bulger ruled the area, very few of Boston’s tourists would have ventured on a bar crawl in Southie. Over the past several years, though, the ghost of Whitey has slowly dissipated and the neighbourhood is home to young professionals and hipsters who have helped transform the area into a thriving nightlife hotspot.

Woody’s L Street Tavern
Famous for getting featured on Anthony Bourdain’s No Reservations, and as a location in the 1997 film Good Will Hunting, the L Street Tavern is a painfully obvious choice for the start of a Southie bar tour. What the choice lacks in creativity, however, it makes up for with its top-notch juke box, good crew of regulars, and unabashedly cheesy back bar. Prior to Matt Damon and Ben Affleck’s appearances, Woody’s was locally famous for its Irish mob connections and tough Southie patrons. Nobody could say the bar has sold out and “gone Hollywood,” though, since other than a surface makeover, it’s still a perfect specimen of a timeless working-class Irish neighbourhood bar.

658 East 8th Street, 617-268-4335

Although the food and drink might be ever-so-slightly dated, the bar room at Amrhein’s is a can’t-miss classic. Boasting America’s first draught tap and the gorgeous, giant hand-carved wooden bar (longest in the country, some say), dating back to 1890, Amrhein’s is a throwback to the classic saloons of the Victorian era. These days, the crowd at this Southie institution is incredibly eclectic, with new residents of this rapidly gentrifying neighbourhood mingling with old regulars, especially around St. Patrick’s Day when savouring at least one pint at the long bar is a long-established local ritual.  


80 West Broadway, 617-268-6189

Whitey’s/Croke Park
To get a feel for what Southie used to be like – pre-gentrification – pop into Whitey’s/Croke Park, a bar that Australian filmmaker Mark Shea named America’s best dive bar. It’s hard not to agree with him, since Whitey’s is one of those hidden local gems that Charles Bukowski would have probably taken up residence in, on account of the friendly regulars, graffiti-covered walls, free pool, and rocking tunes on the juke box. Add to this, a microwave, should you need to warm up some snacks, super-cheap beer specials, heavy-handed free pours, over-sized shots, and a drive-thru Burger King next door. 


268 West Broadway, 617-464-4869

Moonshine 152
Nothing screams gentrification more than a moonshine-themed craft cocktail bar, one of the most recent openings that will have Southie’s original residents thinking, “There goes the neighbourhood.” But with late-night eats such as pork fat popcorn and crispy pig ear, Ron Swanson-themed dinner specials, and Moonshine Mary specials at Monday brunch, we’re sure most everybody will soon be a convert. The focus will be on the chef’s Korean take on New England classics, but with its impressive, stark, and functional bar area, there is considerable buzz over the moonshine cocktails, including a novel kimchi whisky chaser that threatens to end the pickle back’s 15 minutes of fame.

152 Dorchester Ave, 617-752-4191

Local 149
Located in a former union office, this thriving bar is a completely unpretentious, laid-back new classic American bar. Regulars flock to Local 149’s large, rectangular bar area to enjoy good wine and excellent cocktails, or to choose from a very nicely-selected list of great imports and craft beers. This is probably one of the city’s best choices for weekend day-drinking, too, with excellent Bloody Mary, Greyhound, and Mimosa specials that fly out along with fried chicken and waffles and its signature hangover helper, the Lobster MacMuffin. Solid bar food has helped this friendly bar quickly establish itself as a new neighbourhood institution. 


149 P Street, 617-269-0900 

Published Saturday, August 1st 2015

Header image credit: Courtesy Whitey's/Croke Park



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