Boston Pirate Trail

The hidded piratical history of Boston, Massachusetts

Boston Pirate Trail

Boston, Massachusetts 02115, United States

Created By: Simmons University

Tour Information

This pirate walking trail is the final project for On the High Seas, a Simmons University course taught by Stephen R. Berry and Lydia G. Fash that wedded literature and history about piracy. Our understanding of piracy in the course was purposefully broad: we did study buccaneers from the Golden Age of Piracy (1650-1720), and we watched Pirates of the Caribbean, but we also looked closely at the Atlantic slave trade (which was legally denominated piracy in 1808), oceanic exploitation (particularly through whaling), and contemporary piracy and shipping. Throughout all these topics, we queried the definition of “pirate” and considered the rhetorical strength and popular appeal of the term and the associations it conjures.

While it is Revolutionary history that has been publicly memorialized through means of the Freedom Trail, Boston has had a long and close relationship to piracy. As the location of first English-language colonial newspaper and a vital colonial port, eighteenth-century Boston closely followed and disseminated news of piratical happenings. It also hosted—and hanged—a number of pirates. Although the heyday of Caribbean piracy was past, nineteenth-century Bostonians continued being fascinated with pirates. A number of publishers capitalized on this interest with copious cheap novels and books about pirates; in the age before international copyright, others pirated literature from Europe. Piratical magazines and books were read far and wide, including by apprehended pirates (a pirate book was used as evidence in a New Orleanian court room) and whalers (who translates piratical cover images onto whale teeth while cruising for whales). Massachusetts abolitionists like Frederick Douglass (who worked as an agent of the Massachusetts Anti-Slavery Society) were likewise doing all they could to distribute their writings and argue against the piratical institution of slavery. In Douglass’s Narrative of the Life of Frederick Douglass (Boston, 1845), the most famous American slave narrative, Douglass recalls that, imprisoned after a failed escape attempt, he had to endure an inspection by “a band of pirates” (slave traders) who “never looked more like their father, the devil.” The comparison of slavery and piracy was made earlier and further south too: in a passage stricken from the final Declaration of Independence, Thomas Jefferson blamed King George for the “piratical warfare” of the slave trade.

This 3-mile trail takes you back in time to when Bostonians were intimately connected to the ocean, reliant on it for trade and for news. You’ll learn about pirates held, tried, and executed in Boston; enslaved peoples brought to the City; abolitionists fighting against slavery; and the explosion of popular novels through the means of a female pirate captain. Thanks for walking (the plank) with us.

—Lydia G. Fash

Tour Map

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What You'll See on the Tour

You are now on the Long Wharf Pier on the Boston Harbor Walk. If you had a compass, you could look toward the Harbor in the direction at approximately 110°ESE.  Depending on the weather on the day of your visit, you might be able to make ... Read more
You are now standing on Long Wharf, the location that holds special meaning to a one Rachel Wall. The account of Rachel Wall, an American female pirate and the last woman to be hanged in Massachusetts, is just one of many stories of small-s... Read more
Although Charles Ellms’s print house no longer stands today, in the first half of the nineteenth century, 91 Cornhill Street would have found his presses hard at work. Born on June 21, in 1805, on the south shores of Massachusetts Bay, Ch... Read more
The Boston Newsletter, established in 1704, was the first newspaper in America to continuously put out a weekly issue.[1] The first issue printed by the postmaster John Campbell was nothing special, just a single sheet with text on both sid... Read more
As he took control of a small vessel in the Bay of Honduras in 1722, Captain Edward Lowe “hoisted a black flag, and declared war on the world.”[1] This proclamation at the very beginning of his piratical career effectively made him nati... Read more
Boston’s Old State House was built in 1713 to be where the Massachusetts General Court met, and as Boston’s oldest surviving public building, it has a lot of history behind it. It is most famous for being the site of the Boston Massacre... Read more
Benjamin Franklin wrote “The Taking of Teach the Pirate,” a ballad, while he was working at his brother James’s print shop in Boston, the spot where you are currently standing. The ballad that Franklin wrote describes the final fight ... Read more
Here at 17 Court St. you can see a placard detailing the site's significance to Boston, particularly Ben Franklin's apprenticeship in his brother's print shop, yet the site also possesses ties to piracy in publishing. Nathaniel Parker Willi... Read more
The Boston Gaol was built in 1635 and for nearly 200 years remained the town and county jail. Those who found themselves imprisoned here included pirates, Quakers, murderers, rebels and the Salem witches. The conditions were horrid behind t... Read more
Welcome to the site of the Boston Gaol, the first jail in Boston. The gaol housed pirates, slaves, witches, and more during its time. Here, at 26 Court Street where the infamous building stood, the pirate Captain Joseph Bradish (1672-1700) ... Read more
Boston's rich history includes the story of Captain John Phillips, a pirate whose trail location is where the late Boston lawyer William Minot’s office was. The connection between Captain John Phillips and William Minot is not a pleasant ... Read more
From 1846 to 1870, The Flag of Our Union (first called Gleason’s) printed, a weekly newspaper and pamphlet novels at 6 Tremont Street.[1] The Flag of Our Union, located near Boston Harbor and run by Frederick Gleason, provided books for s... Read more
In Granary Burying Grounds sits the grave of a well-known founding father, John Hancock, however, many are oblivious to the disreputable aspects of his career. John Hancock accumulated his wealth by pirating goods with merchant vessels befo... Read more
Located within the Boston Common and a short distance away from the Freedom Trail that runs through the Common is a plaque commemorating the historic Great Elm,. The Great Elm was an American Elm tree that embodied Boston’s particular rep... Read more
The city of Boston is well known for its maritime life and its long history of piracy. Classical pirates invoked fear in the public and were heavily targeted by the law as evidenced by the number of execution sites on this trail. However, w... Read more
You are now at the sight of the Old Charlestown Ferry Landing, most famously known for where six members of Black Sam Bellamy’s crew were hanged for piracy in 1717. On a cold April night in 1717 Sam Bellamy and his crew were sailing north... Read more
On June 30, 1704, Captain John Quelch and six crew members dangled lifeless in the Charles River as a jolly roger in stagnant tropical air.[1] Their bodies served as a warning to sailors: “Do not turn pirate.”[2] Like many classic pira... Read more
Forty-nine years after John Quelch was hanged and his body was displayed in Boston harbor, a slave ship called The Phyllis sailed through this same harbor. Aboard this ship was seven-year-old Phillis Wheatley who was sold to a wealthy Bosto... Read more
Among the many stops on Boston’s Freedom Trail is Copp’s Hill Burying Ground, the second oldest cemetery in the city, in the North End of Boston. The location is also key in author Maturin Murray Ballou’s story of Fanny Campbell, a fi... Read more
We are the literary critics and historians of On the High Seas, a learning community taught by Stephen R. Berry and Lydia G. Fash, at Simmons University. Through that course, which combined pirate literature and pirate history, we authored ... Read more


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