After losing his teaching position in England, Taylor moved to Boston in 1668 as a minister. Taylor took a second degree at Harvard. He achieved his first degree at an English University. After graduating, Taylor became a minister to the tiny frontier town of Westfield Massachusetts.
There were many difficulties in Taylor's life during his time in Westfield. The town was under constant threat of attack during King Philip's War. The Great Indian War also did a large amount of damage
near the Massachusetts Bay. About two-thirds of all the villages on the Bay were damaged or completely destroyed. Taylor's first wife bore eight children five of whom died as infants.
Taylor has written a great deal of poems throughout his life. It is not on record of how many, for poems by him are still being discovered today. Some were recently discovered in his library in the binding of books. Most of which were concerned with religion. In his poems, Taylor tried to defend the original faith of the Puritans against newer, more liberal religious ideas. Taylor's poems differ from other puritan poets in being more difficult and intricate. His main poetic work is a group of more than two hundred poems entitled Preparatory Meditations, which he wrote on and off for forty-four years.
Taylor wrote little concerning his life in the New World. He concentrated mostly on religious beliefs of the puritans in the late seventeenth and early eighteenth centuries.