He was the son of Edward Wigglesworth (born 1603 in Scotton, Lincolnshire) and Ester Middlebrook of Wrawby (born Batley), who married in October 27th 1629 in Wrawby. The family moved to New England in 1638. They originally lived in Charlestown, Massachusetts, then soon moved to New Haven, Connecticut. When Wigglesworth was ten years old his father became bed-ridden, forcing the boy to leave his schooling in order to help maintain the family farm.
He graduated from Harvard in 1651 and taught there as a tutor until 1654, sometimes preaching in Charlestown and Malden, Massachusetts. He became a minister in Malden in 1654 but not actually ordained until 1656.
Wigglesworth believed that he was essentially not worthy of believing in God as a result of merely being human. When he underwent a series of nocturnal emissions in his early life, he was thereafter convinced of his damnation. Through his diaries, he recounts his struggle to remain pure and good, despite continually relapsing into what he viewed as man's natural depravity.
When Wigglesworth became a minister of a church, he was soon overcome with a psychosomatic disorder in which he felt he could, ironically, do everything except preach. His confused and disappointed congregation elected to find a replacement for Wigglesworth, an unnamed preacher who went on to embezzle funds from the church. Thereafter, Wigglesworth was reinstated and encouraged to take up preaching again.
In his diaries, Wigglesworth expresses an overwhelming sense of inferiority. Amongst many, two of the most notable instances that occur are: first with his refusal to accept the presidency of Harvard due to his lack of self-confidence, and again when he married his cousin because, he claims, he is not good enough to find another woman.
Yet he was eventually to marry three wives: Mary Reyner, Martha Mudge and Sybil (Avery) Spearhawk.
In the 1650s, Wigglesworth confided in encoded messages of his diary that he was plagued by homosexual attractions to his male students, which continued even after his marriage. This is documented in the PBS film Out of the Past.
In 1662 he published "The Day of Doom or a Poetical Description of the Great and Last Judgment", a "doggerel epitome of Calvinistic theology", according to the anthology, Colonial Prose and Poetry (1903), that "attained immediately a phenomenal popularity. Eighteen hundred copies were sold within a year, and for the next century it held a secure place in [New England] Puritan households. As late as 1828 it was stated that many aged persons were still alive who could repeat it, as it had been taught them with their catechism; and the more widely one reads in the voluminous sermons of that generation, the more fair will its representation of prevailing theology in New England appear."
Despite the fierce denunciations of sinners and the terrible images of damnation in The Day of Doom, its author was known as a "genial philanthropist, so cheerful that some of his friends thought he could not be so sick as he averred. Dr. Peabody used to call him 'a man of the beatitudes', ministering not alone to the spiritual but to the physical needs of his flock, having studied medicine for that purpose," according to Colonial Prose and Poetry.
Other works by Wigglesworth include God's Controversy with New England and Meat out of the Eater.
This epitaph on Wigglesworth has been attributed to Cotton Mather: