Ask people what the best neighborhood in Boston is, and the South End might end up being the answer you hear the most. It’s gorgeous, it’s home to a lot of great restaurants, and it’s the city’s best place to go when you want to look into windows and steal design ideas from people who have subscriptions to Dwell. What it isn’t though, is a party neighborhood - not compared to Allston or Central Square at least. But that doesn’t mean it doesn’t have great places to drink. From old school pubs to wine bars, here are the best places to get a drink in the South End.
Ideally, a great tiki bar would serve at least 51% of its drinks in glassware that looks like it might be cursed. Shore Leave actually fails on that account, but it succeeds everywhere else. This underground den off Harrison is the dark, tropical escape you need to get you through a Boston winter. Don’t come here just for drinks, though, because you’ll miss a small but good Asian fusion menu (start with the Filipino ribs).
Anchovies looks like a standard little pub that you can find in just about any Boston neighborhood. But standard little pubs usually aren’t filled with people housing baked ziti and linguini with clams at one in the morning. Is this place a dive? An Italian restaurant? A little of both? It doesn’t matter, because it’s the type of easy-going and fun place where you might make new friends by the end of the night. It’s hard to have a bad time here, and that applies whether you’re there for the chicken parm or to sit at the bar by yourself with a beer.
If Anchovies is packed but you still want a tiny, old school bar that seems out of step with its current neighborhood (in the best way possible), head to The Delux. It’s a retro-looking place with strings lights, Christmas trees made out of PBR cans, and a bunch of Elvis memorabilia on the walls. A lot of people will be eating here (surprisingly for a place that looks like it only sells bags of chips, it operates a full kitchen and keeps the menu fresh every few months), but you won’t feel out of place if you grab a booth and just drink for a few hours.
You don’t have to dress up to go to Wink & Nod on Appleton Street, but you might want to in order to fully enjoy this hidden cocktail club that feels like the perfect place to plan your next casino heist. This spot has one of the most extensive selections of fine scotch in the city, but don’t just settle for a glass of something you can buy off a shelf. Instead, go for one of their creative cocktails, like the Death or Glory, which is served on a charred cedar plank.
For the most part, the Southern-ish food at Beehive is just OK. And yet, we love coming here and frequently recommend it to people looking for a cool spot to take out-of-towners. That’s because going to an underground music venue, splitting several bottles of wine, and ordering just enough food so that the server doesn’t get pissed at you while a Latin jazz-funk band plays is always a good way to spend an evening. There aren’t a lot of big places where you can party in the South End, but this is one.
The Gallows on Washington Street is the neighborhood pub every neighborhood should have. If you don’t have one, you can either apply for a small business loan, buy an abandoned Blockbuster, and get cooking, or you can come here and enjoy a comfortable place to drink and one of Boston’s better burgers. One of these is easier than the other, especially since you won’t be able to pull-off the playfully spooky Tim Burton aesthetic they have going on here.
Five Horses Tavern
This wood-paneled spot on Tremont has an expanded pub menu (tacos and pizzas in addition to the requisite burgers and wings), and close to 30 beers on tap, including one rotating cask option. If you haven’t had cask ale before, it’s a little warmer and less carbonated than what you might be used to. It also tends to feel less filling than keg beer, so you’ll at least think you’ll be able to try the other 29 beers for a moment before realizing what a terrible idea that would be.
In a city this old, it’s natural that a lot of places have earned the distinction of being called “institutions.” One of those is Wally’s on Mass Ave, a tiny, brick-walled club that’s the type of place the word “joint” was invented for. You can’t get any food here, but you can get a tumbler full of liquor and hear live jazz every single night without paying a cover. So come to Wally’s and experience a little of what Boston was like when City Hall wasn’t known as the ugliest building in America and JFK was just that nice young congressman with a good haircut.