Samuel Dickinson first married Judith Troth (1689–1729) on April 11, 1710. They had nine children; William, Walter, Samuel, Elizabeth, Henry, Elizabeth "Betsy," Rebecca, and Rachel. The three eldest sons died of smallpox while in London seeking their education. Widowed, with two young children, Henry and Betsy, Samuel married Mary Cadwalader in 1731. She was the daughter of Martha Jones (granddaughter of Dr. Thomas Wynne) and the prominent Quaker John Cadwalader who was also grandfather of General John Cadwalader of Philadelphia. Their sons, John, Thomas, and Philemon were born in the next few years.