Intro: Boston Bars Aren’t Just Places to Drink—They’re Time Machines
Here’s the deal: Boston bars are like a history book written in bourbon, IPAs, and the lingering scent of regret. Whether you’re a tourist clutching a map like a lifeline or a local who’s seen three mayors and a dozen renovations, finding the right bar is 50% vibe, 30% “do they take my insurance?” and 20% “can I order a burger with this?”
But let’s cut through the fluff. This list isn’t about overpriced craft cocktails in a hipster neighborhood where the bartender judges your life choices. These are real Boston bars—places where the bartenders know your name, the jukebox plays Aerosmith, and the beer is always cold. Let’s dive in, shall we?
1. Cheers (The Original ‘Cheers’ Bar)
Cheers, Boston—not the TV show (that’s a different story for a different city). This spot, located at 754 Boylston St., is the OG bar where the series was set. It’s a time capsule: wood paneling, dim lighting, and the kind of barstool competition you only see in Boston. Pro tip: Order a “Sammy” (their beer) and pretend you’re Ted Danson for half a second.
Why it’s a gem? It’s less about the drink menu and more about the experience. The staff here is like a Boston Red Sox fan in the off-season—salty, loud, and slightly overqualified. Plus, it’s got that “I’ve been here since the Reagan era” charm. Home for more Boston bar lore?
2. The Churchill
If you want to sip like a Bostonian with zero pretension, head to The Churchill in the South End. This bar, at 390 Harrison Ave., is the definition of “cool without trying.” They’ve got a killer whiskey list (we’re talking rare stuff you’ll never find in a chain bar), a rooftop that’s Instagram’s favorite new BFF, and a menu that includes truffle fries because, uh, yes.
Pro tip: Ask for a “Churchill Special” (whiskey with a twist of orange and a sprinkle of salt). If the bartender raises an eyebrow, you’re doing it right.
3. The Hawthorne
Okay, now we’re talking about a bar that’s literally a speakeasy. The Hawthorne, at 235 Congress St., is where Boston’s elite go to sip Old Fashioneds and pretend they’re in prohibition-era Chicago. The entrance? A nondescript door in a historic building. The vibe? “I’m in a James Bond movie, and you’re not invited.”
Need a reservation? Absolutely. But since when did Bostonians do things the easy way? Show up at 9 p.m. and hope the bouncer thinks you’re a VIP. If not, hit up Make Your Own Beer and skip the line.
4. The Sinclair
The Sinclair in Cambridge isn’t a bar, but it’s got the vibe of one. Located at 52 Church St., this venue is where bands go to test their music before selling out. The bar here is a side act, but the drinks are solid. Bonus: If you’re lucky, you’ll catch a band playing “Born to Run” at 2 a.m. while sipping a $12 craft beer. Boston, here, is about the experience.
Why These Bars Rule (And What to Order)
- Atmosphere: These bars are not chain stores. They’re local, loud, and have opinions about your political views without being asked.
- Drinks: From craft beers to whiskeys you’ve never heard of, these spots know their stuff. The Churchill’s got a 200-bottle collection. Yes, 200.
- Location: All of these bars are in walkable Boston neighborhoods. Uber is your friend, but so are sidewalks if you’re up for a 2 a.m. adventure.
Pro Tips for Bar Hoppers
- Always ask for a local’s opinion. Bostonians love to talk about their bars. Ask a cab driver, a barista, or a tourist’s ex. Someone will give you the real deal.
- Try the seasonal specials. Bars like The Hawthorne rotate their cocktail menus more than a TikToker rotates their personality. Spring = floral cocktails. Winter = heavy, dark, and brooding.
- Dress appropriately. If you wear yoga pants to The Churchill, you’re not just out of place—you’re a tragedy waiting to happen.
FAQs: Boston Bars 101
What’s the best time to visit Boston bars?
Weeknights. Weekends are for tourists and people who’ve never heard of “quiet hours.” Go on a Tuesday, and you’ll feel like you own the place.
Do these bars have happy hours?
Yes. And no. The Churchill has a 4–6 p.m. happy hour, but it’s more like “we’re pretending it’s happy hour until the manager notices.”
Can I bring my dog?
Only if you’re at Cheers. And even then, it’s a 50/50 shot. Boston bars love dogs, but they hate unleashed dogs. And your emotional support golden retriever.
Outro: Sip Responsibly (Or Don’t, We Don’t Judge)
Boston bars are a vibe. They’re history, culture, and the kind of place where you’ll meet someone who’s seen U2 in 1987 and still regrets it. So grab a drink, toast to the fact that you’re not in a college dorm anymore, and remember: If you can’t find a bar you like, maybe it’s time to Custom Beer with your own brand. Because nothing says “Boston” like a bar named after your ex.
Still thirsty for more? Home for more Boston bar guides. Or, if you’re a bar owner trying to Grow Your Business With Strategies Beer, we’ve got tips that’ll make your drinks taste better.
Sell your beer online through Dropt.beer if you’re feeling ambitious.
