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