Samuel was born in Hatfield, Masschusetts. In 1698, at the age of 11, he was captured by Indigenous warriors during a raid on the town. He was captured again in 1723, in Northfield, Massachusetts. In 1730, he moved to Deerfield, Massachusetts with his wife and infant daughter. His wife and an eight-year-old daughter drowned in 1740, leaving Samuel with three children aged 4-10. He did not remarry.
Samuel enslaved Peter, Fortune, Caesar, and most likely a woman named Phillis. He rented the services of Jonathan Ashley's enslaved men- Titus and Cato, and rented out Caesar to Ashley on at least one occasion. He might also have had Colonel William Williams' enslaved man, Caleb Sharp, do some carpentry work for him, as in his day book entries in 1751, he charged Dickinson for nails and sundries for "Sharp."
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