Boston Beacon Hill: True Crime Walking Tour & Expert Guide

4.85

(177 reviews)

What’s the experience like?

We met right outside the gold-domed State House, and I was honestly still finishing my coffee when our guide, Sam, started with this wild story about a missing doctor. He didn’t sound rehearsed — more like someone who’d actually pored over old newspapers for fun. There were maybe ten of us, and I caught this older couple exchanging glances when he mentioned the Parkman-Webster trial. Apparently, that one’s famous here. Didn’t expect to laugh so much about murder cases (that sounds wrong), but Sam just had this way of making even the darkest stuff feel kind of… human? He pointed out a brick wall where some trial witnesses supposedly argued in the street — you could almost picture it.

The air smelled like wet leaves — classic Boston spring — and we wandered through these Beacon Hill alleys I’d only ever seen in movies. The stones underfoot were uneven, made me wish I’d worn different shoes. Every so often, someone would ask if the Boston Strangler really lived nearby (he did), and Sam would lower his voice for effect. My favorite bit was this tiny side street where he stopped us to talk about an unsolved theft from the 1800s; you could hear someone playing piano through an open window above us. For a second it felt like we’d slipped into another time. There was something eerie but also kind of comforting about being in a group, listening to these old stories while people walked their dogs or hurried home from work around us.

I’m not sure I’ll remember every single detail (there were a lot), but I still think about that moment on Acorn Street — the light was fading and Sam just let us stand there in silence before moving on. It wasn’t what I expected from a true crime tour; it felt more like wandering with a friend who knows all the city’s secrets, and isn’t afraid to share them.