The Best of Boston Cocktail Dens & Supper Clubs

Wood paneling, taxidermy, and a Colt 45-branded digital clock make the Automatic a serious cocktail bar disguised as a dive. Order up a Oaxacan Sunrise made with tequila, mezcal, agave, and Peychaud’s, or a spot-on take of the classic Aviation. The Automatic crew knows their stuff, but that doesn’t mean they’re above making a Frozen Mudslide.

This swanky spot, hidden in the Nine Zero Hotel, serves up cocktails that range from the curious (a Cacio E Pepe Martini made with gouda-infused vodka) to the classic (an expertly crafted Sherry Cobbler and Pink Lady) to the just plain fun (A Sex on The Beach featuring fresh cranberry and peach puree). And if you’ve got a drinking buddy in tow, you can make a Resy to receive a customized, large-format decanter cocktail based on your own preferences. 

It’s easy to see why this Eastern Standard sibling, founded by Jackson Cannon, has become a local institution. From the moment you take your seat, you’ll be treated to some of the best service around and to an ever-changing cocktail menu of classic revivals and envelope-pushing house creations. A menu of classic bar snacks—like shrimp cocktail and steak tartare with black truffle gribiche—also awaits, should those tipples inspire your appetite.

You like gin? Welcome to paradise. Our Fathers stocks over 100 bottles, and has a gin-focused cocktail menu. The many options include classics, like the French 75 and a killer Ramos Gin Fizz, new creations, and a dedicated Martini section with “bone dry,” “extra dry,” “dry,” and “wet” options. And when you start having inevitable, gin-induced hunger pangs, you can quash them with hearty Jewish deli fare, including potato latkes and hand-cut pastrami sandwiches.

At this subterranean spot, which looks like it could have been a Boardwalk Empire set, in Davis Square—120 kinds of whiskey are on offer. The expansive menu of brown spirits offers the option of ordering any pour as a standard, an old fashioned, or a Manhattan. An additional menu of house creations serves up cocktails like the Spaghetti Western (High West Double Rye, Luxardo Aperitivo, Meletti Amaro, and Cocchi Americano) and a flask of house punch that serves two.

A soundtrack of old-school hip-hop and a TV that loops classic Kung-Fu flicks lends this bustling Chinatown cocktail den an atmosphere like no other. Once you get settled, order a Japanese whisky-based cocktail like the Yakuza Old-Fashioned, prepared with Nikka Coffey Grain; or something Tiki like the Kamehameha, with Thai chile-infused vodka and coconut milk.

Descend the flight of stairs to Shore Leave to experience Tiki like never before. Within the jungle-print-wallpaper-clad environs, you’ll encounter a sherry-inspired variation of a strawberry daiquiri; a Negroni-inspired riff on a pina colada; and the eponymous Shore Leave Cocktail, which mixes rum, molasses, and madeira. The food menu is a veritable smorgasbord of pan-Asian delights, featuring karage chicken wings, dan dan wontons, and fried clam bao.