Speakeasy

Question

I'm looking for a speakeasy or old "classic" bar in Boston. Preferably in the North End area.

Quiet, dark, with great martinis and old fashions.

Thanks

Answer

Boston has a rich cocktail culture with several bars that evoke the speakeasy style, perfect for a quiet evening with expertly crafted martinis and old fashions. While the North End is famous for Italian eateries and bustling streets, it also has a few hidden gems and nearby classic-style bars worth exploring.

Here are some top options to consider:

The Baldwin Bar – Located in Woburn (a short drive from Boston proper), The Baldwin is widely regarded as one of the city’s best cocktail bars. It has a dim, intimate setting and is known for its precise craft cocktails, including excellent martinis and inventive old fashions.
Backbar – Situated in Somerville, near Union Square, this bar has a cozy, speakeasy vibe. The bartenders are highly skilled, offering a menu that features both classic cocktails and creative seasonal concoctions. The lighting and decor create a dark, intimate ambiance.
Drink – Located in the Fort Point area, Drink is a small, minimalist cocktail bar that focuses entirely on customized cocktails. You won’t find a traditional menu; instead, bartenders craft drinks based on your flavor preferences. It’s quiet, dark, and perfect for cocktail enthusiasts.
Lookout Rooftop and Lounge – While slightly more modern, this hidden rooftop bar has a speakeasy feel during evening hours, especially in the lounge section. Their old fashions are well regarded, and the atmosphere is more subdued than typical tourist-heavy spots.

In the North End specifically, true speakeasies are rare, as the area is more known for Italian restaurants and cafes. However, you can find classic cocktail bars within a short walk or a few minutes by cab:

Stoddard’s Fine Food & Bar – Just on the edge of the North End, Stoddard’s offers a classic bar atmosphere with a focus on timeless cocktails. It’s not a hidden speakeasy, but it maintains a historic, quiet charm reminiscent of old Boston taverns.
Boston Harbor Hotel’s Rowes Wharf Bar – While slightly upscale, this bar has a dark, cozy ambiance with excellent martinis and old fashions. Perfect if you prefer a refined, classic setting close to the waterfront.

For the authentic speakeasy experience, be prepared to explore nearby neighborhoods outside the North End, such as the South End, Fort Point, and Cambridge. These areas host most of Boston’s hidden cocktail gems where ambiance and drink craftsmanship are prioritized over high foot traffic.