Five Incredible Mixology Spots in Boston

Why we love it: How cool is it to find a sophisticated restaurant just outside the Kenmore train station (and right across the turnpike from Fenway)? Despite all the trendy regulars looking to sip innovative cocktails and ruin their diets with ridiculously tasty butterscotch bread pudding, the vibe at ES remains informal and cozy – even if it does get loud in the evenings and after the ballpark clears out. A great spot to pregame with friends or share a few Bourbon Derby Flips and top shelf Singapore Slings with that special someone, this place is busy for all the right reasons; where the food and drink go down so well you forget about the extra Benjamin you had to drop on the bill. At least until the next morning. 

Why we love it: Anyplace named for one our favorite activities gets high marks off the bat – but this little venue’s dedication to cocktails would make us regulars regardless of its moniker. The talented mixologists behind the vintage bar handcraft everything, and base many of their nightly created cocktails on the specific tastes of each individual patron. As such, this is definitely not a place to visit if you’re in a rush, but it’s easily one of the best spots to find painstakingly personalized cocktails that just might become your regular drink of choice. And for those who would rather play it safe, a Top Ten cocktail list on the wall steers aficionados toward popular nostalgic libations (just in case that mescal, bourbon, blueberry gin, and coffee liqueur combination doesn’t work out).  

Why we love it: Billie Holiday is rad. Decades ago she recorded an album inside this swanky lounge, and even though it was a totally different venue at the time, the giant photo of that crooning jazz goddess by the entrance and the sultry feel of the speakeasy styled main room make us think she’d come back and do it again if she hadn’t gone off to that big rhythmic riff in the sky. A vintage wooden bar and walls covered in red damask give the space a classic old school vibe, so you can tuck in to one of the overstuffed leather booths with a house-blended rum drink or classic Sazerac and pretend the cops are about to knock down the door. And if that’s too staid, the adjacent club space opens up around 9pm, so you can take your intricate craft cocktail to the dance floor and craft a few intricate moves all your own.

Why we love it: Flash’s is purposely kitschy, but in a fun faux 50s diner kind of way. And anyplace that tacks random cutouts of Bettie Page on the wall is on the right track in our book. This carefree hangout attracts a diverse crowd with a vibe that’s worlds removed from the trendy norm at Back Bay watering holes, and the potent “Flash Backs” classic cocktail menu entices everyone from rugged construction workers to Berklee music students to try some of grandpa’s old favorites. The “Flash Forwards” menu, meanwhile, offers tongue-and-cheek creations like the gin and Cointreau-based Bull’s Nuts, and the venue’s assortment of infused bourbons will get a nod from even the most diehard spirit snob.

Why we love it: Green Street is simple in design, ever laid-back in vibe, and a phenomenal place to introduce yourself to artisan drinks that won’t break the bank. The joint attracts a creative crowd of young cocktail aficionados and no shortage of foodies willing to drop $17 on mac & cheese (it’s so worth it!), but if the limited menu of booze somehow manages to bore you, ask for the “secret” extended drinks list packed with more than 100 choices. Once you’ve finally decided on a libation, you can grab a seat next to one of the scattered retro art pieces that account for most of the décor and enjoy a lost art all too rare at popular bars these days: conversation.