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Pirates on the Chesapeake: Being a True History of Pirates, Picaroons, and Raiders on Chesapeake Bay, 1610-1807
Here is a dazzling array of swashbuckling pirates, picaroons, and sea rovers pitted oftentimes against the feckless representatives of an outpost governmental authority in the Chesapeake Bay region. It is an exciting, dramatic 200-year-old history which begins grimly with the “starving time” in the Virginia colony in 1609 and ends, mercifully enough, with the peaceful resolution of the Othello affair with the French in 1807. But, in between these two very different events lies a full panoply of grisly and bizarre buccaneering incidents one is hard pressed to imagine from the vantage point of the late twentieth century. For example, twice in the 1600’s large Dutch fleets sailed boldly into the Chesapeake attacking and burning. Then there was the French pirate chief Lewis Guittar who crossed swords with a Virginia colonial governor, a duel which ended in a climactic sea battle in Lynnhaven Bay. Having completed impressive research in the archives of the Netherlands, England, and United States, Shomette skillfully reconstructs these episodes and many others, including the intensive anti-pirate cruises to capture – dead or alive – the notorious Blackbeard. The anti-pirate cruises led to the roundup of dozens of pirates and some showy executions but did little to curb the continued terrorist activities of bandits like Roger Makeele, Stede Bonnet, and Joseph Wheland. Mr. Shomette is a staff member of the Library of Congress, a lecturer, and an acclaimed underwater archeologist. Author of ‘Shipwrecks on the Chesapeake’, ‘ Battle for the Patuxent’, ‘London A Brief History’, and ‘Shipwrecks of the Civil War’, he has also writtten numerous articles on the Chesapeake and its history.
- GenresHistoryPiratesNonfiction
352 pages, Hardcover
First published January 1, 1985
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About the author
Donald G. Shomette
17 books10 followersDonald G. Shomette is a marine archaeologist and cultural resource manager.
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Displaying 1 - 11 of 11 reviews
August 18, 2025
Piracy was an important part of the story of the Chesapeake Bay region, as Donald Shomette makes clear in his 1983 book Pirates on the Chesapeake. This engaging book – Being a True History of Pirates, Picaroons, and Raiders on Chesapeake Bay, 1610-1807, as its colonial-style subtitle puts it – fairly brims over with exciting stories of seaborne robbers, of their victims, and of the authorities who sought to end the pirates’ careers of high-seas crime.
Shomette, a Library of Congress staff member and underwater archaeologist, is also a prolific author of works relating to the maritime history of the Chesapeake region, and the thoroughness of his research makes for a book that is well-grounded as scholarship whilst also being entertaining as popular history.
As Shomette makes clear, the history of piracy on Chesapeake Bay, which began within just a couple of years of the establishment of the Jamestown Colony in 1607, involves some of the most notorious sea robbers in history. In April of 1699, Virginia Governor Andrew Nicholson and his council “were directed to be on the lookout for a buccaneer named William Kidd”. Yes, that is the Captain Kidd, “a former pirate-hunter commissioned to track down buccaneers off Madagascar and in the Red Sea, [who] had himself gone on the account, taking and plundering numerous French, Moorish, and Portuguese ships as he went” (p. 100).
Governor Nicholson’s piracy-related concerns no doubt increased “when word arrived from Captain Thomas Wellburn, Sheriff of Accomac[k] County, that Kidd had arrived on the coast. Wellburn, it seemed, had learned from Matthew Scarburgh, Collector of Customs for the Eastern Shore, that he had been informed of Kidd’s arrival on the Delaware by two ex-pirates…from…a secluded pirate retreat near Lewes [Delaware]” (p. 101). The pirates were said to have two ships with about 130 men, with so much stolen booty on board that “each of their company had a share valued at £4,000” (p. 101).
Governor Nicholson certainly had much to worry about. A pirate fleet with half a million pounds’ worth of stolen swag, just three counties away from his colony? It would have been a short sail for Captain Kidd, down the Delmarva coast and up through the Virginia Capes, to raid and plunder as he saw fit. Fortunately, however, the warnings about Captain Kidd constituted a bit of a false alarm, as the pirate captain instead sailed north toward Boston, was caught, and was hanged in England in 1701. Shomette closes this early part of his history by noting somberly that “On the Chesapeake Bay, unfortunately, there would be no breathing spell, for the worst pirate invasion in its history was already underway” (p. 102).
The two decades that followed are known among historians as the “Golden Age of Piracy.” Governments like that of Great Britain, faced with costly and protracted conflicts like Queen Anne’s War (1702-13), frequently outfitted privateers – ships that attacked and confiscated vessels of the enemy’s merchant marine under the cover of law. A successful capture of an enemy ship secured a share of the profits for privateer captains who engaged, in wartime, in what basically constituted a sort of legalized piracy. Once such wars were over, ex-privateers often found that they liked the work they had been doing, and switched over into careers as full-fledged pirates.
Such may have been the case for Edward Teach, or Blackbeard, whose reign of terror from 1716 to 1718 is also a part of the history of piracy in the Chesapeake region. The Virginia Capes – Cape Charles at the bottom of the Delmarva Peninsula, and Cape Henry at the northeastern edge of what is now the city of Virginia Beach – were at the northernmost end of the zone where Blackbeard carried out his piratical depredations, and Blackbeard took a number of ships in Virginia waters.
Blackbeard’s life and career have sometimes been romanticized. Robert Earl Lee’s biography Blackbeard the Pirate: A Reappraisal of His Life and Times (1974) fairly bursts with admiration for Teach’s bold and uncompromising nature; and actor Ian McShane’s energetic portrayal of Blackbeard in Pirates of the Caribbean: On Stranger Tides (2011) presented Teach as a compelling, almost tragic figure with formidable supernatural powers. Shomette, who has no patience for the romanticizing of Blackbeard’s image, informs us that “Teach toyed with brutality almost as an avocation” (p. 203), and adds that “Blackbeard’s appetites were bestial” (p. 199). The examples that he provides in support of both of these claims are horrifying.
Because Blackbeard enjoyed a degree of unofficial protection, courtesy of the colonial governor of North Carolina, it was Virginia’s colonial governor, Alexander Spotswood, who ultimately took action against Blackbeard. Shomette praises Governor Spotswood as “a true pirate fighter” (p. 203) for sending Lieutenant Robert Maynard and the sloop Jane to engage Blackbeard at the pirate’s Ocracoke Island hideout in November of 1718. The Battle of Ocracoke Island was exceedingly bloody (29 of Maynard’s crew of 64 were killed or wounded, along with dozens of Blackbeard’s pirates), but Blackbeard was killed and his piratical career was ended.
Piracy in the Chesapeake continued right up through the American Revolution, when Tory picaroons (from the Spanish picaro, meaning “rogue”) raided patriot settlements. The American victory at Yorktown in October of 1781 did not put a stop to these depredations. In February of 1782, a picaroon force led by Joseph Wheland Jr. attacked the town of Benedict, Maryland, plundered it, burned homes, and took 12,000 pounds of salted pork, along with clothing, furniture, and other miscellaneous goods, as well as taking away a number of enslaved people (although it is not clear whether those people were set free or carried into slavery elsewhere). One John Senior, who had been captured by Tory pirates the year before, was chagrined at being a prisoner again:
As the marauders rummaged about, indiscriminately plundering Benedict, John Senior confronted the gaunt picaroon chieftain. Wasn’t he the notorious Wheland, the same man who had made Senior a prisoner the summer before? Wheland laughed and asked the man “if he had used him ill.” Walking over to [John] Ferguson’s house, the picaroon wrote in bold red letters across the wall: “Joseph Wayland Commander of the Sloop Rover.” (pp. 300-01)
Yorktown victory or no Yorktown victory, “The Chesapeake situation was reaching a critical point. Governor [Samuel] Paca wrote in exasperation to General Washington describing the dismal state of affairs” (p. 301). Not until the news of the signing of the Treaty of Paris in 1783 reached the bay watershed did “the hated picaroons of the Chesapeake” cease their activities.
Published by Tidewater Publishers – a now-defunct publishing company that, from its headquarters in the Eastern Shore town of Centreville, Maryland, long published a wide array of regional works about the Chesapeake – Pirates of the Chesapeake provides a rich bounty of stories for armchair pirates and pirate-hunters everywhere.
Shomette, a Library of Congress staff member and underwater archaeologist, is also a prolific author of works relating to the maritime history of the Chesapeake region, and the thoroughness of his research makes for a book that is well-grounded as scholarship whilst also being entertaining as popular history.
As Shomette makes clear, the history of piracy on Chesapeake Bay, which began within just a couple of years of the establishment of the Jamestown Colony in 1607, involves some of the most notorious sea robbers in history. In April of 1699, Virginia Governor Andrew Nicholson and his council “were directed to be on the lookout for a buccaneer named William Kidd”. Yes, that is the Captain Kidd, “a former pirate-hunter commissioned to track down buccaneers off Madagascar and in the Red Sea, [who] had himself gone on the account, taking and plundering numerous French, Moorish, and Portuguese ships as he went” (p. 100).
Governor Nicholson’s piracy-related concerns no doubt increased “when word arrived from Captain Thomas Wellburn, Sheriff of Accomac[k] County, that Kidd had arrived on the coast. Wellburn, it seemed, had learned from Matthew Scarburgh, Collector of Customs for the Eastern Shore, that he had been informed of Kidd’s arrival on the Delaware by two ex-pirates…from…a secluded pirate retreat near Lewes [Delaware]” (p. 101). The pirates were said to have two ships with about 130 men, with so much stolen booty on board that “each of their company had a share valued at £4,000” (p. 101).
Governor Nicholson certainly had much to worry about. A pirate fleet with half a million pounds’ worth of stolen swag, just three counties away from his colony? It would have been a short sail for Captain Kidd, down the Delmarva coast and up through the Virginia Capes, to raid and plunder as he saw fit. Fortunately, however, the warnings about Captain Kidd constituted a bit of a false alarm, as the pirate captain instead sailed north toward Boston, was caught, and was hanged in England in 1701. Shomette closes this early part of his history by noting somberly that “On the Chesapeake Bay, unfortunately, there would be no breathing spell, for the worst pirate invasion in its history was already underway” (p. 102).
The two decades that followed are known among historians as the “Golden Age of Piracy.” Governments like that of Great Britain, faced with costly and protracted conflicts like Queen Anne’s War (1702-13), frequently outfitted privateers – ships that attacked and confiscated vessels of the enemy’s merchant marine under the cover of law. A successful capture of an enemy ship secured a share of the profits for privateer captains who engaged, in wartime, in what basically constituted a sort of legalized piracy. Once such wars were over, ex-privateers often found that they liked the work they had been doing, and switched over into careers as full-fledged pirates.
Such may have been the case for Edward Teach, or Blackbeard, whose reign of terror from 1716 to 1718 is also a part of the history of piracy in the Chesapeake region. The Virginia Capes – Cape Charles at the bottom of the Delmarva Peninsula, and Cape Henry at the northeastern edge of what is now the city of Virginia Beach – were at the northernmost end of the zone where Blackbeard carried out his piratical depredations, and Blackbeard took a number of ships in Virginia waters.
Blackbeard’s life and career have sometimes been romanticized. Robert Earl Lee’s biography Blackbeard the Pirate: A Reappraisal of His Life and Times (1974) fairly bursts with admiration for Teach’s bold and uncompromising nature; and actor Ian McShane’s energetic portrayal of Blackbeard in Pirates of the Caribbean: On Stranger Tides (2011) presented Teach as a compelling, almost tragic figure with formidable supernatural powers. Shomette, who has no patience for the romanticizing of Blackbeard’s image, informs us that “Teach toyed with brutality almost as an avocation” (p. 203), and adds that “Blackbeard’s appetites were bestial” (p. 199). The examples that he provides in support of both of these claims are horrifying.
Because Blackbeard enjoyed a degree of unofficial protection, courtesy of the colonial governor of North Carolina, it was Virginia’s colonial governor, Alexander Spotswood, who ultimately took action against Blackbeard. Shomette praises Governor Spotswood as “a true pirate fighter” (p. 203) for sending Lieutenant Robert Maynard and the sloop Jane to engage Blackbeard at the pirate’s Ocracoke Island hideout in November of 1718. The Battle of Ocracoke Island was exceedingly bloody (29 of Maynard’s crew of 64 were killed or wounded, along with dozens of Blackbeard’s pirates), but Blackbeard was killed and his piratical career was ended.
Piracy in the Chesapeake continued right up through the American Revolution, when Tory picaroons (from the Spanish picaro, meaning “rogue”) raided patriot settlements. The American victory at Yorktown in October of 1781 did not put a stop to these depredations. In February of 1782, a picaroon force led by Joseph Wheland Jr. attacked the town of Benedict, Maryland, plundered it, burned homes, and took 12,000 pounds of salted pork, along with clothing, furniture, and other miscellaneous goods, as well as taking away a number of enslaved people (although it is not clear whether those people were set free or carried into slavery elsewhere). One John Senior, who had been captured by Tory pirates the year before, was chagrined at being a prisoner again:
As the marauders rummaged about, indiscriminately plundering Benedict, John Senior confronted the gaunt picaroon chieftain. Wasn’t he the notorious Wheland, the same man who had made Senior a prisoner the summer before? Wheland laughed and asked the man “if he had used him ill.” Walking over to [John] Ferguson’s house, the picaroon wrote in bold red letters across the wall: “Joseph Wayland Commander of the Sloop Rover.” (pp. 300-01)
Yorktown victory or no Yorktown victory, “The Chesapeake situation was reaching a critical point. Governor [Samuel] Paca wrote in exasperation to General Washington describing the dismal state of affairs” (p. 301). Not until the news of the signing of the Treaty of Paris in 1783 reached the bay watershed did “the hated picaroons of the Chesapeake” cease their activities.
Published by Tidewater Publishers – a now-defunct publishing company that, from its headquarters in the Eastern Shore town of Centreville, Maryland, long published a wide array of regional works about the Chesapeake – Pirates of the Chesapeake provides a rich bounty of stories for armchair pirates and pirate-hunters everywhere.
May 27, 2017
This book, though basically interesting local history of Pre-Revolutionary Colonial America and through the age of the English Civil War to the time of the American Revolution, loses the story along the way. The opening is rather slow and there are many quotes of the era in [SIC] format. Though this can have an impact on the events as they are written, it simply became too much for me to continuously read of the events in this format as quotes were recorded within. The fun part of this book (and there are several) is when we cross the time of the infamous “Blackbeard.” I am of the impression that this book is terrific for people who may have been raised within the North Carolina to Chesapeake and Maryland/Virginia areas; but, this book wouldn’t keep much appeal for people outside of this geography due to the way the content was presented throughout. The maps aren’t particularly interesting and I could have done without the editorial drawings (there is no clear reference in the bibliography as to where these were attained from) that were made of the era would have been better served had the author received copyright authorizations to reprint (by photo insert) of the various Pirates and Colonial Governors. Still, there were some very interesting points of discovery, the map the author created (and inserted on pages 190-191) was outstanding; however, one map doesn’t cover the method of the overall story – the story is missing due to the author’s attempt to the overbearing historical account and recorded words and legal actions taken. Simply put, it missed the mark and I cannot put my thumb on this exactly. I am still glad I read this book however, it did bring parts of Virginia and Maryland to life of the past.
This book was a loaner from a good colleague who has in some manner a direct link to parts of the near end of the book. Understandably, when any person has or can link a book to their own existence in any form it becomes personal, and any person will feel the attachment in a strong sense to them in some degree. To my colleague – he’s a great man and fellow. My colleague “dog-eared” a couple of pages and I scolded him for doing this when he lent me the book (jokingly of course with tongue in cheek style.)
In the end, very interesting local history that requires an author to “tell the story” and refrain from so many [SIC] quotations. This book did shed better light on the works of Daniel Defoe; I took notes on some of the reference material and brief discussion points along the way. It is here of the time frame specifically that Daniel Defoe adds value as to the witnessed accounts of the era of long ago.
This book was a loaner from a good colleague who has in some manner a direct link to parts of the near end of the book. Understandably, when any person has or can link a book to their own existence in any form it becomes personal, and any person will feel the attachment in a strong sense to them in some degree. To my colleague – he’s a great man and fellow. My colleague “dog-eared” a couple of pages and I scolded him for doing this when he lent me the book (jokingly of course with tongue in cheek style.)
In the end, very interesting local history that requires an author to “tell the story” and refrain from so many [SIC] quotations. This book did shed better light on the works of Daniel Defoe; I took notes on some of the reference material and brief discussion points along the way. It is here of the time frame specifically that Daniel Defoe adds value as to the witnessed accounts of the era of long ago.
July 26, 2021
Dry in parts but absolutely magnificent in others (like the American Revolution chapters), this book only has two main shortfalls. First, there's not enough political economy here. Explaining where stolen cargoes are sold is half of any good explanation of piracy in some or other place or time, and this book is so eager to get out to sea that it just leaves that stuff under-discussed or straight up ignored. Second, it uses months as it's narrative unit ("by January... that March.... In December") but it frequently leaves out the years. With voyages or wars that span multiple years, it's gratingly vague to say something happened "in March." Which March - March of that year, or the next year, or what? This is a small thing but it happened enough really get irritating by the end of the book, which left things on a regrettably sour now.
December 21, 2017
Four stars for the information, two stars for the academic writing. We've all heard about pirates in the Caribbean, but they were right here in the Chesapeake for a couple of hundred years. I knew some of the pirates from elsewhere, and some of the stories have been used in books such as Chesapeake and Roots, so it was interesting to read about them in a true historical context. Locals to the area will also recognize many places and many people known for other things. I found it mostly enjoyable, but people not familiar with the Bay or with ships from the colonial era would probably find it too much of a struggle.
February 6, 2018
Dense, good for someone who is into military history (troop movement types). A good resource for researchers. Not something that reads smoothly cover to cover.
January 5, 2021
A wonderful read. Full of adventure and knowledge.
November 30, 2025
Interesting and informative. Lots of fun facts buried in here.
January 10, 2022
A bit dry but a good reference for research
March 4, 2009
One doesn’t normally think of pirates being in Maryland and Virginia but water borne criminals were, according to this book, active in the Chesapeake area during colonial and early republic times. The Tidewater area grew a lot of tobacco and shipped it to England to get trade goods in return. All of this trade was carried by ship. European conflicts caused the area to be afflicted by privateers of England’s enemies and to have its vessels become privateers as well. Privateering was essentially a legalized form of piracy. Like current definitions of guerrillas, your view of whether it was legal or not depended on where you sat. As plantations and towns got larger, richer, sea raiders would descend upon them to wreck havoc. During the Revolutionary War these sea raiders generally fought for the British and were composed of Tories, but as the war started coming to a close these sea raiders also attacked Tory owned plantations. This work provides an interesting look at a little known segment of American history.
January 12, 2015
This book appealed to me because I have an ancestor from the Eastern Shore who fought in the Revolutionary War. So lately I've been reading all sorts of books about Maryland in the Revolution.
Pirates on the Chesapeake gave some really good insight into what happened in that area from the early days until 1807. This book assumes that the reader has some knowledge of nautical terms and ships in general. Sadly, that wasn't the case for me.
Overall, I did enjoy this book. It is well-researched and well-written. It is valuable from a historical standpoint alone.
Pirates on the Chesapeake gave some really good insight into what happened in that area from the early days until 1807. This book assumes that the reader has some knowledge of nautical terms and ships in general. Sadly, that wasn't the case for me.
Overall, I did enjoy this book. It is well-researched and well-written. It is valuable from a historical standpoint alone.
February 3, 2009
Fascinating.
Displaying 1 - 11 of 11 reviews