The novel is a satirical epic of the colonization of Maryland based on the life of an actual poet, Ebenezer Cooke, who wrote a poem of the same title. The Sot-Weed Factor is what Northrop Frye called an anatomy — a large, loosely structured work, with digressions, distractions, stories within stories, and lists (such as a lengthy exchange of insulting terms by two prostitutes). The fictional Ebenezer Cooke (repeatedly described as "poet and virgin") is a Candide-like innocent who sets out to write a heroic epic, becomes disillusioned and ends up writing a biting satire.
The novel is set in the 1680s and 90s in London and on the eastern shore of the colony of Maryland. It tells the story of an English poet named Ebenezer Cooke who is given the title "Poet Laureate of Maryland" by Charles Calvert. He undergoes many adventures on his journey to Maryland and while in Maryland, all the while striving to preserve his innocence (i.e. his virginity). The book takes its title from the grand poem that Cooke composes throughout the story, which was originally intended to sing the praises of Maryland, but ends up being a biting satire based on his disillusioning experiences.
Ebenezer Cooke is the son of Andrew Cooke, an English merchant who owns a tobacco (or‘sot-weed’) plantation at the settlement of Malden in the colony of Maryland. Along with his twin sister Anna, Ebenezer is tutored privately by a young man named Henry Burlingame III. Later, while Ebenezer is studying at Cambridge University, he is reunited with Henry who reveals his past life as an orphan, travelling musician and seaman. Henry recounts a tale of saving a mother and daughter from pirates, and then persuades Ebenezer to travel to London, where Ebenezer decides that his true vocation is to be a poet.
While ill, Andrew Cooke grants power of attorney to Ebenezer and reveals that, after the death of their mother, Ebenezer and Anna were nursed by a woman named Roxanne Edouarde.
In London, Ebenezer declares his love for the prostitute Joan Toast, but refuses to pay her fee, and confesses to being a virgin. Joan’s pimp and lover, John McEvoy, subsequently informs Andrew that Ebenezer has been leading a dissolute life, so Andrew sends Ebenezer and a servant, Bertrand Burton, to Maryland. From devotion to Joan, Ebenezer swears to remain a virgin. Before his departure, Ebenezer visits Charles Calvert, LordBaltimore, who is the Governor of Maryland, and offers his services as a Poet Laureate of the colony. Calvert is bemused, but grants the commission. Ebenezer decides to write an epic poem entitled “The Sot-Weed Factor”.
On the coach to Plymouth, Ebenzer encounters one Peter Sayer, who is really Henry in disguise. Henry reveals that, while trying to ascertain his true identity, he has become embroiled in the politics of Maryland, but has discovered that he was adopted as an infant by one Captain Salmon, after being found floating on a raft in Chesapeake Bay. He has also obtained part of a journal which reveals that his grandfather, Henry Burlingame I, took part in an expedition led by Captain John Smith that was attacked by Indians. In order to save his own life, and that of Burlingame, Smith undergoes a sexual trial with Pocahontas, the daughter of the Indian chief Powhatans. At this point, the journal breaks off, and Henry explains that he is searching for the remaining sections of the document.
In Plymouth, Henry leaves Ebenezer, who is terrified by a sinister pair of seamen called Skye and Scurry who declare that they are pursuing a man by the name of Ebenezer Cooke. Ebenezer boards his ship, the Poseidon, only to find that his identity has been assumed by Bertrand, who is fleeing London because of an affair with a married woman. In order to escape detection, Ebenezer agrees to exchange places with Bertrand on the voyage. Bertrand then loses Ebenezer’s savings by gambling with the Reverend Tubman and a young woman named Lucy Rowbotham. The Poseidon is captured by pirates led by a Captain Pound, and Ebenezer and Bertrand are taken on board their ship, which then attacks another ship, the Cyprian, which is loaded with prostitutes. The pirates rape the female passengers, and Ebenezer is tempted to rape a woman who reminds him of Joan. Captain Pound has Ebenezer and Bertrand thrown overboard, telling them that he has heard that someone by the name of Ebenezer Cooke has already arrived in Maryland.
Expecting to drown, Bertrand tells Ebenezer that he has wagered away to Tubman the whole of the Malden estate. The pair make it to shore where they free a bound black man named Drepacca, and treat the wounds of an elderly Indian chief named Quassapelagh. They meet Susan Warren, a female swineherd who also reminds Ebenezer of Joan. Susan claims that she has been debased by Captain William Mitchell, and that she is acquainted with Joan. Ebenezer meets both Captain Mitchell and his son Tim, who turns out to be Henry Burlingame III in another disguise. Ebenezer and Henry visit Father Smith, a Jesuit priest who owns part of the journal sought by Henry. Smith relates how he was told by an Indian named Charley Mattasin the tale of Father Fitzmaurice, a missionary who fathered three children on Indian women of the same tribe. The journal gives further details of the capture of Captain Smith and Henry’s grandfather, but in order to discover more, Henry turns next to locating a cooper by the name of William Smith.
At the next settlement, Ebenezer witnesses a chaotic outdoor court in session. He hears how William Smith was once indentured to a man named Ben Spurdance and how Spurdance tried to swindle Smith out of his share of land upon expiry of his indenture. The court is about to find in favour of Spurdance, but an outraged Ebenezer insists that the court punish Spurdance by signing the rights to Spurdance’s land over to Smith. The judge agrees and gets Ebenezer to sign a document, whereupon Ebenezer discovers that Spurdance is the overseer of Malden, and that his father’s estate has now passed to Smith. Ebenezer meets Mary Mungummory, a prostitute who was once the lover of the Indian Charley Mattasin. He hears that John McEvoy has travelled to Maryland in search of Joan Toast, and meets Thomas Tayhoe, a man who has been indentured to William Smith because of trickery on the part of McEvoy. Ebenezer offers to exchange places with Tayhoe, and this plan is accepted by Smith on the condition that Ebenezer marries Susan Warren. After the marriage, Susan reveals that she is really Joan Toast.
Upon hearing that his father is due to arrive at Malden, Ebenezer flees in the company of one Nicholas Lowe, who turns out to be Henry in yet another disguise. Henry reveals that Anna is in Maryland and Ebenezer resolves to find her. Upon arrival in the town of St Mary’s, Ebenezer encounters Bertrand, who has again been posing as Ebenezer. Bertrand has become the lover of Lucy Rowbotham, who had married the Reverend Tubman only to discover that Tubman was already married. Because of the wagers made on board of the Poseidon, Tubman and Lucy both believe they have a claim on Malden.
After deciding to return to Malden, Ebenezer and Bertrand commission a boat skippered by Captain Cairn. During a storm, they shelter upon Bloodsworth Island, where they are captured by a community of rogue slaves and rebellious Indians that is dedicated to waging war against white men. Another prisoner is John McEvoy. They meet Drepacca and Quassapelagh, but are threatened with execution by Chicamec, king of the Ahatchwoop people. Ebenezer mentions the name of Henry Burlingame, whereupon Chicamec suspends their execution. Ebenezer is allowed to read a journal that gives a further account of the adventures of John Smith and Henry Burlingame I.The journal relates how Burlingame became chief of the Ahatchwoops by winning an eating contest. Furthermore, Burlingame– who has a remarkably small penis - uses Smith’s egg-plant recipe in order to impregnate the wife he marries as chief. The child is Chicamec himself, who then takes as his bride a young woman who is the descendant of Father Fitzmaurice. He has three sons; one of whom is white-skinned; another golden skinned; and a third dark-skinned. The first he names Henry Burlingame III and places on a raft. The second and third, Chicamec states, fell in love with white women, and betrayed the Ahatchwoops. Ebenezer calculates that the dark-skinned son became Charley Mattasin, who loved Mary Mungummoryand was executed for murder.
Ebenezer strikes a deal with Chicamec whereby, after leaving Bertrand and Captain Cairn as hostages, he will attempt to trace Chicamec’s surviving sons and bring them to Bloodsworth Island. After leaving the island, they encounter Mary who, along with the trapper Harvey Russecks, explains that a golden-skinned Indian by the name of Billy Rumbly is living with a white English woman. They then encounter Harvey’s brother, Harry,a crooked and violent miller who is jealous of his wife, Roxanne, and daughter, Henrietta. McEvoy plays a trick on Harry that results in Harry becoming gravely injured. It transpires that Roxanne and Henrietta are the mother and daughter who were saved from the clutches of pirates by Henry years earlier. Billy Rumbly arrives and is astonished to hear that his father and lost brother are still alive, but is reluctant to take steps to prevent the imminent conflict with the Indians and slaves. Rumbly leads Ebenezer to his cabin where it transpires that Rumbly’s partner is Anna. After hearing ofAnna’s affection for Henry, Rumbly decides to return to Bloodsworth Island, accompanied by McEvoy. Ebenezer and Anna discover that Roxanne is their former nurse and that Henrietta is their half-sister.
McEvoy returns with Bertrand and Captain Cairn but claims that Rumbly has now sided with the Indians and slaves. Ebenezer and Anna decide to return to Malden along with McEvoy, Henrietta, Bertrand and Roxanne. Their boat is seized by the pirate Ben Avery and the men forced to swim to shore. The women are freed after Ben Avery recognizes Roxanne as a former lover.At Malden, the ownership of the Cooke estate is decided by a court presided over by Governor Nicholson. The claim by Lucy Rowbotham and her father are rejected. By way of a legal nicety, Malden passes back to the Cooke family because of Joan Toast’s marriage to Ebenzer. William Smith and his lawyer Sowter are threatened with imprisonment, but are released after presenting Henry with more of the journal that tells of his ancestor’s fate. Together with a fragment held by Joan, this reveals the egg-plant recipe by which Smith and Burlingameincreased their penis size and enabled them to fulfil their sexual challenges.
Ebenezer and Joan consummate their marriage, and Joan falls pregnant. Burlingame leaves for Bloodsworth Island in order to quell the rebellion. He returns in Indian guise with the intention of marrying Anna but leaves once more and does not return. Anna falls pregnant, but is saved from disgrace when Joan and her child die in childbirth and Anna’s child is reared as Ebenezer’s.Ebenezer’s poem, ‘The Sot-Weed Factor’ is published to some acclaim, but the poet refuses to write any more verse until many years later.