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Colonial Sudbury, Massachusetts, was designated the Puritan Village by author Sumner Chilton Powell in his 1964 Pulitzer Prize–winning history of the founding of this quintessential New England town in 1638. Yet this quiet rural village also had a darker history that is often overlooked. Sudbury’s Puritan inhabitants, including some of the most prominent citizens in town, held and sold enslaved Black people throughout the seventeenth and eighteenth centuries. Stories gleaned from preserved records highlight the lives of men, women and children held in bondage, including a court case involving an enslaved boy repeatedly beaten and left scarred by his master less than thirty years after the town’s founding, as well as the bill of sale of Phebey, age two, to a woman in another town. Local author Jane Sciacca uncovers the hidden side of suffering in this New England town.