The complicated Tom Jones–like plot is interwoven with numerous digressions and stories-within-stories, and is written in a style patterned on the writing of 18th-century novelists such as Henry Fielding, Laurence Sterne, and Tobias Smollett.
The novel is a satirical epic of the colonization of Maryland based on the life of Ebenezer Cooke, who wrote a poem of the same title.
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.
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.
In London, Ebenezer declares his love for the prostitute Joan Toast, but refuses to pay her fee, and confesses to being a virgin.
Before his departure, Ebenezer visits Charles Calvert, Lord Baltimore, who is the Governor of Maryland, and offers his services as a Poet Laureate of the colony.
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 Captain Salmon, after being found floating on a raft in Chesapeake Bay.
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.
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.
Bertrand then loses Ebenezer's savings by gambling with the Reverend Tubman and a young woman named Lucy Rowbotham.
Hearing that his father is due to arrive at Malden, Ebenezer flees in the company of Nicholas Lowe, who turns out to be Henry in yet another disguise.
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.
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.
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.
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 Burlingame increased their penis size and enabled them to fulfill their sexual challenges.
"[6] Barth spent four years writing the original version of the book; it was published by Doubleday in 1960, consisting of about 800 pages.
With The Sot-Weed Factor, Barth returned to earlier novel forms, both in their structure and mannerisms as well as in the irony and imitation found in Miguel de Cervantes' Don Quixote and Fielding's Shamela.
[7] Critics generally consider The Sot-Weed Factor to mark the beginning of a period in which Barth established himself at the forefront of American literary postmodernism.
[8] Time included it in its list of the 100 best English-language novels from 1923 to 2005, where Richard Lacayo called it "Dense, funny, endlessly inventive".
[13] Postmodern author Thomas Pynchon includes in his novel Mason & Dixon several excerpts from a fictional poem, the Pennsylvaniad, a clear reference to The Sot-Weed Factor's Marylandiad.