The Dark Side Of Boston Walking Tour

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Get off the Freedom Trail and explore the darker side of Boston! This original guided walk through misery, misfortune, malevolence and murder is based on true historical events that have occurred in Boston. Fact is often stranger than fiction! As you begin to uncover Boston's dark side, you will hear many dark and disturbing stories not often shared with tourists. Topics include but are certainly not limited to: the scourges of smallpox and the Great Influenza, the dangers of Richmond Street, the vandalization of the Royal Governor's House, the Molasses Flood, body snatchers, and the infamous Brink's Robbery, all against the backdrop of Boston's oldest neighborhood. Winding among the labyrinth of the North End’s small streets and alleys is a great way to get off the beaten path and explore a delightful neighborhood. It's even better when treated to stories of death and misery from Boston's checkered past. Crime, disease, death, and disaster... what better way to enjoy a pleasant evening in Boston!

Meeting Location

Meet your guide at the corner of Hanover and Cross Streets, Boston (the statue of boxer Tony DeMarco across from the Greenway).


Saturdays - 6:00 PM
Sundays - 6:00 PM

Please visit our calendar at for specific dates, times and registration links.

Private Tours: This tour can be scheduled as a private tour at any time with advance notice. Private tour rates apply. Call 617.367.2345 or visit to learn more.