Our Walking Tours

Boston is a walking city, and a city steeped in almost four hundred years of history. Accordingly, there are some fantastic walking tours to choose from. While you could choose a traditional Freedom Trail tour, the secret is that the Freedom Trail is easy to self-guide! Boston Strolls travels off the beaten path, literally, to give you a glimpse into Boston’s past that goes beneath the surface and beyond the ordinary. What you will find below are tours that explore fascinating tales that are too often overlooked. We look forward to sharing them with you.  

Beacon Hill Uncensored

We will stroll through Boston Common and the scenic streets of Beacon Hill as we discuss the seedy past of this now upscale neighborhood and the more colorful characters whose mark on history is often overlooked – a sleepwalking murderer and Boston’s earliest known nudist, just to name a few!

North End Underground

Now known for its world-famous cannoli and beautiful brick facades, the North End has long been a hotbed for questionable activity. Nearly 400 years of history give us fascinating tales of pirates, anarchists, and the rebel leaders that launched a revolution.

Back Bay Deconstructed

Stroll from Boston’s colonial coastline at the foot of Boston Common to the heart of the “new” neighborhood in Copley Square. Along the way, we’ll discuss the technologies that enabled the city to tackle this ambitious project, the personalities and institutions behind it, and the innovative building techniques that transformed the Back Bay from salt-marsh to skyscrapers.

Boston Unexplained

Get into the holiday “spirit” with our newest stroll in honor of Halloween. If you long for the days of Mulder and Scully, enjoy a little mystery with your history, or simply want an excuse to get the gang together for a night of tingly tales followed by pumpkin beers, this is the tour for you.

Bad Medicine

Boston has been a leader in scientific discovery and innovation ever since the first Resurrection Men began digging up cadavers for ambitious medical students. The fields of medicine, anatomy, and forensics all experienced significant advancements right here in Boston. On Bad Medicine, you will learn about the strange occurrences and interesting discoveries, the innovators and the charlatans, that have left their mark on history.