The good news about drinking in Downtown Boston is that you have plenty of options. The bad news is that most of them are either places with the words “Ye Olde” in the sign, or hotel bars patronized by people whose Twitter feeds consist solely of golf commentary, complaints about in-flight wifi, and retweets of Jeanine Pirro with a “makes you think...” tacked on.
That’s why we spent months drinking our way through Downtown to narrow down the list of 10 spots below. Some serve cocktails that involve so many obscure ingredients you suspect the bartender made a few of them up, while others are places that serve you beer in a plastic cup. But all of them are great places to go, and not just between 5-7pm for your co-worker’s goodbye celebration.
Democracy Brewing has, hands down, the coolest looking space of any Boston brewery. Instead of an aluminum warehouse that smells like yeast, it looks and feels like an old world beer hall. The beer is very good (though they don’t brew any New England IPAs and they get a little snippy if you ask about them), and they serve flights, so you can try them all in one visit. It’s also the unique place that’s good for both groups or just a couple people, thanks to big communal tables to accommodate the former, and small semi-hidden booths for the latter.
We’re not sure what the theme of Better Sorts Social Club is (hunting lodge from the future, maybe?). But we know we love grabbing a couch seat, briefly considering whether we’re tripping when we see a picture of a deer wearing a smoking jacket on the wall, and then diving into what is definitely the most creative selection of cocktails in the neighborhood. Any place that can make a martini made with pasta water taste good is worth spending time in.
Some people call Biddy Early’s a dive, but that’s not really true. It feels more like a homey small town pub than a place where the paramedics regularly swing through. After work, it’s packed with people who stop for beers before catching a train at South Station, but in the afternoons you’ll find that it’s a perfect place to blow off work for a few hours, drinking a Guinness and playing Golden Tee.
The ratio of people in Downtown Boston drinking light beer to people drinking crisp Chablis is high enough to break math. But thankfully, the wine-drinkers have a hell of a place to go in Haley.Henry. This Downtown Crossing spot is tiny, as if your parents turned your childhood bedroom into a shrine for natural wines after you went to college (heartbreaking, but understandable). It has a nice small menu of tinned fish and charcuterie type stuff, but we prefer to spend our money on the wine, especially since they’ll open any bottle for you if you commit to ordering at least two glasses.
The back room at Carrie Nation isn’t a speakeasy in the sense that you have to walk through a working toilet stall to get to it, it’s just down a long hallway and a little hard to find. Once you manage to find it, though, you’ll sip cocktails in what is essentially a 1920s gambling den, complete with vintage lamps, pool tables, and semi-hidden leather booths. There’s no one named Snakes with a set of brass knuckles in his vest pocket, but the cocktails are great, and the fact that many of them cost $11 is even greater.
Barracuda feels less like a bar and more like the attic of a friend who installed taps in his house (which, fun fact, is something Joshua Jackson did in real life, demonstrating the type of vision that made him the obvious choice to captain Minneapolis’s District 5 pee wee hockey team). It’s hidden down an alley, one level above street level, and filled with the type of junk you buy at a yard sale and then can’t figure out what to do with, like, for example, an actual rowboat that’s hanging from the ceiling for some reason. They have a seafood-heavy menu, which almost no one in the place is brave enough to order from, but you should be coming here to drink beers and relax - as long as it’s not right after work on a Friday, when it will probably be uncomfortably packed.
People having been drinking at The Marliave in Downtown Crossing for over 100 years. That in and of itself is not a reason to make this list (you can say the same thing about the underside of the railroad bridge heading to South Station, and it didn’t make the cut) but it’s a pretty good sign that this place is doing something right. With big leather booths, cocktails named after 19th-century socialites, and a space that never gets uncomfortably crowded, the downstairs bar here is low-key but still feels classy. It’s our favorite spot in the neighborhood for a drink and a dozen oysters.
It’s hard to say what the best part of Roxanne’s is, and that’s a really good sign. All of the cocktails here are $10. It feels like a members-only club in the South Pacific. And the food here is a complete afterthought, so you can sit and drink for hours without getting side-eyed by a server for not ordering a burger. Put it all together and it’s one of the best places in Downtown Boston to grab a drink and catch up with a friend.
Despite its name, you shouldn’t be coming to Bushwood Cocktail Club for cocktails - they’re nothing special. For that matter, the beer selection isn’t particularly noteworthy, either. You’re coming here because it’s fun to blow off steam playing pop-a-shot with friends (just a few of them, though, this place is tiny). It’s technically an arcade bar because it’s filled with everything from Skeeball and Buck Hunter to Scrabble and Battleship, but it’s not annoying in the way that a lot of those are, because the games feel like a natural part of the atmosphere rather than the bar’s whole reason for existing.
To be clear: you have to be in the right mood for Yvonne’s. If you’re feeling a little cynical about the world because, you know, it’s the world, then a speakeasy filled with a lot of people taking bathroom selfies with the caption “hating me doesn’t make you look better” isn’t going to be what you want. But if you’re in a mood to embrace pink chandeliers, drinks named after Carly Rae Jepsen songs, and an entrance that, for no apparent reason, takes you through a fake hair salon, then the flashiest restaurant in Boston is here for you. There are three bars to choose from (including one that’s hidden behind a fake bookshelf), and you’ll find one to have fun in - even if you don’t take a single bathroom selfie.