Where Would the Mad Men Drink In Boston?

By Michelle Pizzo | May 19, 2019 | Food & Drink

We found The Hub’s swankiest cocktail lounges fit for Don Draper and the Sterling Cooper gang to set down their fedoras and sip an after-work drink.

Wink & Nod

This chic South End speakeasy serves craft cocktails alongside a rotating menu in collaboration with local chefs. Rich hues of red and gold, with lavish accents of wood and marble, add to the seductive, vintage atmosphere; perfect for one of Don Draper’s signature trysts. 3 Appleton St., 617-482-0117; winkandnod.com

Bogie’s Place

Old Hollywood bravado makes a comeback at Bogie’s, nestled behind curtains in the back of JM Curley’s. The intimate lounge serves up prime dry aged steaks, like the popular New York Strip, a 12 oz. steak, dry aged for thirty days. Enjoy alongside a perfect classic martini with a twist of lemon rind. 21 Temple Pl., 617-338-6333; bogiesplace.com


Relive the Prohibition era with artisanal, craft cocktails, and select white, red, and sparkling wines. The historic wool warehouse-turned-cocktail bar is the perfect local for a Mad Men-worthy happy hour. Simply tell the bartenders a few of your favorite cocktail ingredients (rum? bubbles?) and they will make you a custom cocktail. 348 Congress St., 617-695-1806; drinkfortpoint.com

No. 9 Park

Sip on an Old World wine from France, Italy, Australia, or Germany at this elegant former Boston townhouse, with breathtaking views overlooking Boston Common at sunset. The perfect spot for a sophisticated evening, the bar offers a simultaneously traditional and innovative program of refined cocktails (they make the best French 75 in the city), skillfully fashioned using the freshest ingredients. 9 Park St., 617-742-9991; no9park.com

Strega Waterfront

Hidden behind the bar you’ll find the speakeasy, a secret room which seats only ten. This completely private space is ideal for a drink or a rendezvous. Try the White Cranberry Gimlet in the spirit of Peggy. 1 Marina Park Dr., 617-345-3992; stregawaterfront.com

Photography by: Photography courtesy of Justin Ides (Drink)