Boston Freedom Trail Pub Crawl: 4 Historic Bars & Local Beer

4.91

(988 reviews)

What’s the experience like?

We ducked under the gaze of Sam Adams’ statue outside Faneuil Hall—honestly, it felt like he was watching to see if we’d pick the right beer. Our guide, Mike, had that Bostonian dry wit and immediately started tossing out bits of history I swear I never learned in school. The first pub was all polished wood and low ceilings; you could smell something malty in the air before you even sat down. I went for a local IPA (maybe too hoppy for me, but when in Boston…). Someone from Dublin at our table tried to order “something revolutionary” and Mike just grinned and poured him a Sam Adams.

The whole crawl was just two blocks—so close that by the second bar, we were joking about whether it even counted as exercise. Each place had its own vibe: one was crowded with Sox fans (they kept glancing at the TV), another quieter, almost candle-lit. At one point, Mike told this story about colonial spies using taverns to pass messages—I’m still not sure if he made it up or not, but it stuck with me. There was this old map on the wall that looked like it had seen more spilled beer than actual history lessons. We laughed a lot more than I expected for a “history tour.”

I didn’t try to pronounce any of the street names—Boston accents are their own thing—but I did ask about how much of the original trail is left. Turns out most of these pubs have been standing since before America was America. The last stop had sticky tables and someone playing blues guitar near the window. Walking back out into the night air (a little chilly, honestly), I realized how much I’d actually learned between sips—and how easy it is to feel like part of Boston for an evening.