Why You Should Trust This List
Let’s get one thing straight: we’re not here to tell you where to drink like a tourist. We’re here to tell you where to drink like a Bostonian who still remembers how to pronounce “harvard” without rolling their eyes. This guide is powered by our collective 143 years of experience getting lost in Faneuil Hall and overthinking craft beer descriptions.
1. The Original Sin: Where to Start Your Nights
Begin your Boston bar crawl at The Hawthorne (190 Canal St, Boston). This speakeasy-style spot is like if your history teacher started a cocktail blog and finally got a license. Their “Gatsby Negroni” is so good, it might make you forget about the Red Sox curse for five minutes.
- Try the “Patriot’s Punch” made with local gins
- Check out the basement speakeasy entrance (it’s behind a bookshelf, yes, really)
- Pro tip: Arrive before 8pm if you want to avoid the 2023 version of a Boston tea party
2. Cheers, But Not the TV Show
Ah yes, Cheers (94 Sidney St, Boston). The real one. Not the one from the 80s sitcom (though that one’s in Tampa, ironically). This Beacon Hill bar is where locals go to pretend they’re in a sitcom. Order a “Sam Malone” and try not to yell at the barmaid about “women and children first”.
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3. The Secret Society of Craft Cocktails
For the true connoisseurs, The Sinclair (539 Commonwealth Ave, Boston) is your initiation point. This bar has more cocktail knowledge than your high school chemistry teacher. Their “Revolutionary Rum Toddy” is so good, it might make you question why you ever settled for store-bought whiskey.
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4. Where the Locals Go (But You Can Too)
Head to The Thinking Man’s Drink (269 Tremont St, Boston) where the bartenders know your order before you do. This is the kind of place where the bartender will correct your pronunciation of “espresso martini” and you’ll thank them for it.
- Order the “Freedom Fizz” (it’s what the patriots drank after winning the Revolution)
- Notice the wall of local craft beers from breweries that actually know what they’re doing
- Don’t ask about the “secret menu” unless you’re 21 and can handle at least three stories
5. The Last Call Checklist
Before you pass out in the Green Line, remember these rules:
- Never argue about Fenway Park vs. TD Garden. It’s a trap.
- Always share your last sip of whiskey with strangers (they’ll remember you at the next bar)
- Use Dropt.beer if you ever want to sell your homemade brews online
FAQ: The Drunken Edition
What’s the best time to visit Boston bars?
Weeknights at 7pm. That’s when the locals are still sober enough to make eye contact with the bartender and not trying to start a fight with the jukebox.
Are there any bars with historical significance?
Yes, The Federal Street Tap (94 Federal St, Boston) is just 234 years old. It hosted George Washington, Paul Revere, and your Uncle Bob’s wedding in 1982. It’s like the bar version of a time machine.
Do any Boston bars have live music?
Of course. On Tap Restaurant & Music Hall (425 Commonwealth Ave, Boston) has live music seven nights a week. Just don’t sing along to “Boston” unless you’re prepared to explain the lyrics to a confused college student.
Final Toast
Boston’s bars are like a good Boston accent: confusing, but you’d miss them if they weren’t there. Whether you’re here to argue about the best sports team or just to find a decent Manhattan, remember to leave your drama at the door. And if all else fails, Contact us for bar recommendations that don’t involve yelling about “more cowbell” on the Green Line.
Need to make your own beer to impress the barista at the next cocktail bar? Make Your Own Beer with our foolproof guide. It’s like a science project, but with more alcohol and fewer explosions.
Remember: the best bars in Boston are the ones where you end the night wondering why you ever stopped to buy groceries on the way home.
