Get off the Freedom Trail and walk into 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.

Photograph of Copp's Hill Burying Ground.

“The dates of five tombstones were altered, about seventy years ago, by the late George Darracott, at that time quite young, so as to make 1690 read 1620, and 1695 read 1625.

“The tombstones removed from where paths were made, were placed in other parts of the ground near by, thus utterly failing to accomplish their true end. Before this great wrong was perpetrated, petty deeds of the same character were frequent. Stones were taken away to be used in the construction of chimneys, to build drains, to cover the openings of tombs, and to place in the bottoms of vaults of coffins to rest upon.

“But the work of destruction has been extended to the tombs, several of which have at some time been controlled by enterprising undertakers, who have removed the remains once deposited to await a resurrection of a totally different character, and used the space thus obtained for the prosecution of a traffic, that of letting out temporary burial space which, at one time, was far more lucrative that it is now.”

Edward MacDonald
Superintendent, Copp's Hill
1891
Copp's Hill Burying Ground. Photo by Tom Coppeto 2010.

On this tour through Boston's Dark Side you will hear many dark and disturbing stories they like to keep from the tourists. Topics include but certainly not limited to the dangers of Richmond Street, the scourges of smallpox and the Great Influenza, the vandalization of the Royal Governor's House, the Molasses Flood, and the infamous Brink's Job all against the backdrop of Boston's oldest neighborhood where the corpses on Copp's Hill moved around more dead than alive.

Photograph of Copp's Hill Terrace in Boston's North End.

Copp's Hill Terrace
Charles Eliot 1897

Charles Eliot, a landscape architect of the firm Olmsted, Olmsted & Eliot, worked tirelessly to provide Boston with open recreational space and laid the foundation for the Boston Metropolitan Park System. He also wanted to create a small reservation in one of the most densely populated quarters of old Boston. His plan included a beach, park, and terrace in Boston's North End.

Charles Eliot died of spinal menangitis several months before the project was complete. Following a severe headache, Charles likely suffered a high fever while speaking incoherently and losing the ability to move his neck. The infection may have also created a reddish rash on his arms and legs while gangrene set in as some of his body tissue decayed from lack of proper blood circulation. Eliot would have spent some time in a coma before expiring.

A lurking Dark Side docent. Proceed with caution. Photo by Tom Coppeto 2010.

Winding among the labyrinth of small streets and alleys in the North End 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.

Photograph of Henchman Street in Boston's North End.

Daniel Henchman was a schoolteacher at Boston Latin teaching children how to read and write. In 1675, at the start of King Philip's War, he was appointed captain of the 5th Boston Company of the Colonial Militia.

“This last night in the close of it I marched to Hassanamesit with 22 men mounted [...] I ordered some to fire, hollowed and ran on as fast as we could, my Lt. first got to the wigwam and received a mortal shot at the dore [...] I called upon my men to fall on and shute into the wigwam, which no more doing, them up with me fell off: I cryed of them for the Lord's sake to stay, for in retreating as we did I gave up myself and them with me for lost [...]

“I cannot inlarg but begging a sanctified use of this and former frowns, for we might and had an opportunity to cill all in the wigwam off.”

D. Henchman
November 10, 1675

Beware, you may run into a henchman along the way. Photo by Tom Coppeto 2010.

We hope you join us for a walk on the Dark Side. Crime, disease, death, and disaster... what better way to enjoy a pleasant evening in Boston! Just don't come alone.

Boston By Foot Brochure listing Boston tours in 2013 season Boston By Foot Guided Walking Tours For Boston By Foot Docents. Those Dark Side guides might be going a bit too far.