The Best Cocktail Bars in Boston

At this point, Boston should be downright proud of its first-class cocktail scene. We might have gotten a late start compared to some other cities (even though we’re home to the country’s first distillery) but these days we can hold our own against any Grade-A cocktail city. Beyond the many superlative drink menus at restaurants around town, there are legions of spots devoted primarily or entirely to mixing up the perfect elixir. Make 2020 the year of drinking well -- and drink deep from the well of these superlative spots. 

Downtown
It was only a matter of time before Naomi Levy made her next move. The multi-award-winning former Eastern Standard star -- who cemented her mixology legacy with seasonal, travel-inspired cocktails -- has taken over the onetime Highland Lounge space and considerably upped the ante. Where Highball Lounge was fun and serviceable, Better Sorts is sophisticated and bold. Levy’s cocktails celebrate food: pear, seaweed, arugula, and hot pepper jelly (!) are some of the outre ingredients you’ll spot on the drink menu. And while the actual food menu skews towards the snack side of things, the short rib Wellington and the burger topped with duck fat roasted onions both make for splendid entrees. 

South End
If Trader Vic’s met a speakeasy, you’d end up with Shore Leave -- a cheeky, underground tiki bar from the team behind nearby Bar Mezzana. Enter through the inconspicuous side door, wind your way down a few flights of stairs, and emerge into the tropics. The decor is that of a moody beach bar -- bamboo wall trim, wooden shingles, palm fronds wallpaper. As for the drinks, traditional tiki cocktails are merely a jumping off point for elixirs like Air Conditioned Eden (a pineapple-infused martini with Bianco and dry vermouths, Agricole rum, and a molasses-based gin from Germany). Yes, the drinking vessels are epic -- think ceramic skulls and coconuts -- and the food is great, too. We are still dreaming of the dan dan wontons.

Roxbury
Brothers Dave and Will Willis had already changed the city’s cocktail scene with its craft spirits, but now they’ve gotten into the bar act themselves. It’s a New Orleans-like lair -- a gothic, 26-seat affair decorated with Prohibition-era spirit bottles. You can grab a velvet booth or sit at the bar and gaze through the huge window at the distillery’s 750-gallon copper pot still. The best news? Most cocktails -- all made with BB spirits, natch -- are just $11.

Harvard Square
If it’s a continuation of Michael Scelfo’s genius you seek, you can do no better than heading upstairs from Alden & Harlow. Scelfo took the former, beloved Cafe Algiers space and created a hangout that feels both new and well-worn, with huge, original windows behind the bar, marble tables, and exposed brick walls. The cocktail names take inspiration from the staff’s favorite albums and songs (hence the menu being called a “track list”), and the drinks themselves play with unexpected ingredients like carrot butter and tomatillo.

Union Square
Bow Market is making it increasingly difficult to drink anywhere else in town. The latest addition to the Inman Square institution is an intimate crowd-funded space that’s part art gallery, part draft cocktail enclave. Peruse the mounted wares of a local creative work while you browse a menu of almost a dozen seasonal cocktails on tap -- or heck, order a simple off-menu cocktail, because they can do that for you, too. Bring in some snacks from another local Bow Market vendor and you have yourself a mellow, erudite evening.

Fenway
Hojoko could have rested on its kitschy, scorpion bowl laurels and called it a day. But this year it made its loyalists even happier with the addition of The Groove, a Tokyo-style record bar within the restaurant. The energy is distinctly analog: warm 1970s decor, curated vinyl from local authorities, live music, and highballs on top of highballs (sake and champagne, too). Psst: the space is also available for private rentals.

Union Square
Those who go out to see comedy usually stick to beer or suffer through watered-down drinks, but Variety Bar, inside the Comedy Studio at Bow Market, seriously raises the bar (we had to). Naomi Levy, the award-winning genius most recently behind Better Sorts Social Club, has helped create one of the most unexpected watering holes in the city, an in-club, Lilliputian cocktail lounge that’s also open to non-ticket holders. Play a little mini-pool and enjoy one of its seasonal concoctions, including the rotating draft cocktail.

Fenway-Kenmore
Jackson Cannon should get a gold medal for transforming the city’s cocktail scene (and share the podium with Brother Cleve, a freelancing bartending legend). When ES opened in 2005, Cannon introduced local folks to the full canon of cocktail making: quality spirits, freshly made mixers, proper glassware. Reams of Sox fans have been ordering Jack Roses and Sazeracs ever since, and subsequent bar managers have played with more inventive ingredients to deepen the massive bar’s drinking experience.

Fenway-Kenmore
Jackson Cannon’s second act. With Eastern Standard’s program well-established, Cannon moved down the street to a homey, living room space devoted almost entirely to masters-level imbibing. The massive leather-bound menu breaks cocktails down by spirit, so that vermouth or gin aficionados can narrow down their selection rather than sitting there frozen by choice. For those who need their evening assured, The Hawthorne accepts reservations earlier in the evening.

Central Square
Old-timers remember this place as the Enormous Room, a perfectly acceptable nighttime hangout that is far more alluring as its current incarnation. The upstairs speakeasy (no signage; just follow the bearded, plaid-wearing crowds) celebrates locally made spirits, seasonal ingredients, and a relaxed approach to imbibing -- you’re here to savor, not quaff. Don’t be surprised if you miss your dinner reservation because you have to order just one more. 

Fort Point Channel
If you’re someone who struggles with too many choices, Drink is your dream. The subterranean, bar -- named 2013’s "World's Best Cocktail Bar" at the Tales of the Cocktail Spirited Awards, among other accolades -- has no actual cocktail menu. Instead, your bartender asks about your preferred spirits and flavors and concocts a delightfully bespoke drink just for you. Given the labor involved -- even the ice-chipping process is protracted -- you’ll savor every last sip while you mull over your next order.

Union Square
Want to prove our cocktail bona fides to visitors? Lead them down a back alley and an unmarked hallway to libation nirvana, then watch them grudgingly embrace Boston as a legit drinking city. Backbar solidified Union Square’s hipster rep, but don’t let that dissuade you: the drinks menu is all about quality, not hype, and the plaid-clad bartenders legit know their business. Takeovers, industry nights, and small-group bartending classes help further solidify the place as ground zero for sophisticated imbibing.

Woburn
One of the city’s best cocktail bars scenes exists in a nondescript suburb 30 minutes outside the city. Thank Ran Duan for your astronomical Uber bill but, we promise you, a visit here is so worth it. Duan took over the bar program at his parents’ suburban Chinese restaurant in 2009 and made Baldwin a must-visit for anyone in search of old-school cocktail revivals, such as pisco punches with pineapple vinegar and the award-winning Father’s Advice (rum, amaro, vermouth, sherry, creme de banana). Things get even more creative in the Baldwin & Sons Trading Company, a second lounge where it’s all kitschy glassware and dry ice effects. Duan also performs his mixology magic at Sichuan Garden, his parent’s second restaurant in Brookline Village, and has another project percolating for 2020, a cocktail bar focused on seafood that will be called Ivory Pearl.

Central Square
Did you know that Green Street owns the area’s oldest liquor license, dating back to the Great Depression? This might explain why the space has earned true "institution" status. Don’t let the Budweiser sign fool you: The tucked-away Central Square spot is where aficionados go when they tire of cocktail newbies crowding the bar of the moment. Drinks are well-considered and well-priced (under $10, by and large). Stay for dinner to justify a few more.

South Boston
Looking for locavore drinking? Drinks are slung mere feet away from the place where many of their ingredients are created, including vodka and flavored liqueurs (almond, cranberry). Bar manager Steve Schnelwar, late of Tavern Road, oversees the intimate venture, open Thursday to Sunday. Shuffleboard and foosball make it easy to make a night of it.

Downtown
The much-adored Downtown barroom is home to a thoughtful variety of creative cocktails and a small-but-stellar selection of brews, if that's your thing. But you really should put a serious dent in the cocktail list. There’s even one of the best burgers in town on the menu to soak up all your liquid debauchery. Plus, a free bubble hockey machine in the back! Bourbon lovers, be on the lookout for one of the best whisky smashes in town.

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