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, and Caesar. In September of 1749, Dr. Thomas Willliams treated a "negro boy" enslaved by Dickinson. This might have been one of these three men at a younger age. Dickinson also 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 daybook entries in 1751, he charged Dickinson for nails and sundries for "Sharp." On September 20, 1759 storekeeper Elijah Williams charged Dickinson for two quarts of rum for a woman named Phillis. Samuel Barnard enslaved a woman by that name and it is possible that Dickinson bought the rum for her.
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