Similar to Boston’s architecture, today’s best cocktail bars in the city mix old-school flair with modern taste, creating innovative concoctions influenced by the ingredients of yesteryear.
Much of Boston’s booze scene is inspired by a bygone era when speakeasies reigned supreme due to Prohibition laws of the 1920s. Even the libation destinations that skew more towards modern mixtures and contemporary atmospheres still utilize traditional secrets of the trade. Check out these cocktail bars in Beantown for a bit of Gilded-Age history, countless creative concoctions and unusual ingredients that are sure to make your taste buds dance.
Wink and Nod
Bar, Restaurant, American, Vegetarian, $$$
“Good spirits” is the slogan of Wink and Nod, a speakeasy-style cocktail bar located in Boston’s South End. At this bar, ingredients such as cordials, fresh juices and infusions are all created in-house daily. Fancy something stronger? Wink and Nod’s Scotch Club meets once a month at different distilleries where they learn about and sample each place’s top-shelf scotch. Taste and savor some of Scotland’s best whiskies, sought after by collectors and in many cases only found at Wink and Nod. Pair your drink of choice with a culinary experience thanks to the bar’s Incubator Program. Every six months, a new restaurant featuring an up-and-coming chef in the area comes in to run the kitchen and serve up innovative dishes to complement the bar’s creative cocktails.
Co-owned by Boston legends Jarek Mountain (Back Bar Harry’s and Abby Lane) and Ken Casey (frontman of the Dropkick Murphys – famously known for the song ‘Shipping Up to Boston’), Lion’s Tail is another of the South End’s best speakeasy-style watering holes. Named for Mountain’s favorite Prohibition-era beverage, the Lion’s Tail drink menu is straight from the pages of your treasured (adult) storybook, with adventurous and whimsical drink options featuring curious flavors and enticing ingredients. On certain Wednesdays, Lion’s Tail hosts a version of #WCW, featuring female bartenders from all around Boston who will shake things up for the night and donate a portion of the evening’s proceeds to the charity of their choice.
Don’t be spooked by the chillingly macabre aesthetic of this Boston-bred gastropub and the first of the Gallow Group’s three distinct local eateries. Once the site of public hangings in Boston’s South End, The Gallows dresses the part to remember its dark history, with taxidermy ravens and one wall decorated like a Ouija board. Simple, natural ingredients such as grapefruit, molasses, pomegranate and lavender add delicious nature-inspired flavors to each drink. The clever naming of The Gallows’s booze selection plays into the eerie atmosphere, with concoctions such as Skin & Bones and Hunting Season enticing the most courageous of cocktail connoisseurs.
Cocktail Bar, Restaurant, Cocktails, American, $$$
A swanky speakeasy in the heart of Downtown Crossing, Yvonne’s exudes an elegant aesthetic from a bygone era. The gold-gilded decor and antique chandeliers transport you back to a time of feather dresses and pinstripe suits, while the exposed-brick walls of the underground venue give the feel of the best-kept secret in town. Once the site of the iconic Locke-Ober restaurant, the space became a landmark known for its elite clientele and discreet Gatsby-esque parties over 150 years ago. Make reservations to enjoy cocktails with dinner in the library room. Alternatively, grab a seat at the dramatic high-top bar to sip on worldly wine and clever cocktails by the glass or from a large crystal bowl to share.
There’s a strong chance you may find standing room only at this popular Downtown Crossing cocktail and burger bar. Named for the early 1900s charismatic yet controversially jailed Boston mayor, James Michael Curley, the bar has a set of playful “law & order” bar rules, including “don’t be a douchebag.” Its robust drink list features intriguing ingredients, blending everything from blueberry and Coors Banquet to Cynar and Aztec chocolate for an explosion of flavors that cocktail connoisseurs love. And like all good, classic speakeasies, jm Curley has a little secret – a hidden 1920s-style steakhouse behind the “Adults Only” sign just past the bar.
A rotating menu of craft cocktails called “The Bookmark” will keep you guessing each time you visit The Hawthorne. Located in Kenmore Square, the bar combines comfort and elegance in its aesthetic, complete with communal tables as well as more intimate settings with plush couches and cozy chairs. During the summer months, take your beverage to the patio for Swizzle Sundays, where guest bartenders and all-stars in the industry create a tiki-inspired cocktail party until sundown. If you want to try being a bartender for a day, The Hawthorne offers mixology classes and seminars to master the perfect concoction.
Cocktail Bar, Restaurant, American, Vegetarian, Vegan, $$$
Don’t be surprised to spot a celebrity or two while sipping on craft cocktails at the iconic Eastern Standard. Both stars and residents flock to this modern-day French brasserie for its delectable cuisine and creative drinks. Its lengthy beverage list features Eastern Standard originals, classics and seasonal selections to surprise you with new flavors each time you visit. Jackson Cannon, the owner of The Hawthorne, is behind this delicious list of adult drinks. Make sure to stop by both locations to sample the innovative inspirations of one of Boston’s best bar directors.
There’s one thing that sets Drink apart from the rest of Boston’s best cocktail joints – there are no menus. General manager Ezra Star doesn’t want to limit her drink list to a few pages. Instead, the possibilities are endless. Your mixologist for the night invites you to take a chance with your taste buds. Feel free to chat with the bartender and give an idea of your cocktail flavor profile. Do you like something sweet? Maybe a bit stronger? Perhaps with a hint of spice? Whatever you’re craving, the booze specialists at Drink have something up their sleeves to make sure you leave satisfied.
Down a back alley in Somerville’s up-and-coming Union Square, you’ll find a discreet red door opening into a brick building on the backside of Bronwyn restaurant. Walk down the desolate hallway to the door at the end, where a small illuminated sign with the words Backbar hangs brightly against the dark black wood. Open the door, walk inside and prepare to be amazed by artistic murals coloring the sky-high walls, kitschy decorations from another era and a set of booths running the length of each wall of the small space. Ready for an adventure? Its cocktail list depicts the origins of Backbar’s global-inspired drinks, with worldly ingredients and creative names such as The Heart-Shaped Herb from Wakanda and Dumbledore’s Office from Hogwarts.
While technically a global tapas restaurant in Cambridge’s Central Square, it would be remiss not to mention the exotic cocktails of Little Donkey. Its drinks feature ingredients from Ireland to Asia and everywhere in between. Transport yourself to an island with the Castaway or enjoy a taste of Japan with the Kyoto Kreamsicle. Curious to sample a classic Bostonian concoction? If a little seafood with your spirits sounds intriguing, sample the area’s local oysters prepared in a shooter with your choice of alcohol, bloody mary mix and lime. After a few of these wanderlust-inspired libations, you’ll feel as though you’ve traveled around the world and back again without ever leaving your barstool.
Bar, Restaurant, American, Vegetarian, Wine, Beer, Cocktails, $$$
Dim lighting and industrial accents give this Boston speakeasy its classic character. The only challenge? Finding the entrance. Brick and Mortar in Central Square doesn’t exactly stand out on the street – there’s no signage to indicate its existence. In true speakeasy form, this cocktail joint can only be found by word of mouth (or a tell-all travel article). Once you arrive at 567 Massachusetts Ave in Cambridge, you’ll find two doors: one marked “Central Kitchen” and the other unmarked. Head through the latter and up the stairs. Here, you’ll find yourself in front of a cozy horseshoe-shaped bar. Take a seat and let the mixologists work their magic on your Love Buzz or Naked Lunch libation as you peruse the delicious treats on its food menu.