Nathaniel and his brother Samuel, Jr. jointly owned a farm in Deerfield, Massachusetts. An active and outspoken Tory, Nathaniel saw his estate confiscated in 1776, and sold in 1781. He fled to New Brunswick, Canada, where he was living by 1786, and never returned. As a result, his enslaved man, Caesar Bailey, became the property of his brother, Samuel, Jr. The Dickinson brothers shared Cato (also known as Dick Cato,) Caesar's wife Hagar, and possibly a girl.