Richard Dale was born in Portsmouth parish, Norfolk County, Virginia, the eldest son of Winfield Dale, shipwright and merchant, and Ann Sutherland. His father died when Dale was ten years old. Two years later, Dale signed on with a merchant vessel owned by an uncle that took him to Liverpool, England. Upon his return to Virginia, Dale became apprenticed to a ship-owner, through whom he made several journeys to the West Indies. Within five years, he achieved the rank of chief mate on a valuable brig. He remained in the merchant service until the spring of 1776.