The family history starts with John Pickering, Edward’s first American ancestor, who emigrated from Yorkshire, England, with his wife, Elizabeth, in 1636, and settled in Salem, Massachusetts, after spending several years in Ipswich. Within a few years John Pickering had acquired several dozen acres of land outside of Salem, on which he established the family home. Only two children—John and Jonathan—are known to have survived childhood. John Pickering’s oldest son, John, was born in Salem. As the oldest son, he inherited most of his father’s property, where he resided with his wife Alice and five children—John, Benjamin, William, Elizabeth, and Hannah. Not only was he a capable farmer, continually adding acreage to the family estate, but he was also a devoted civic servant, filling a variety of offices, including constable and town councilman. He also served as a lieutenant in the local militia, distinguishing himself in the Indian War of 1675, also known as King Phillip’s War. Like his father, John Pickering bequeathed the family farm to his oldest son, also named John, who became a well-respected citizen of Salem, filling the office of city councilman as well as representing the area in the Massachusetts General Court. He, too, expanded the family estate, willing portions of it upon his death to his wife, Sarah, and their six children—John, Theophilus, Timothy, Lois, Sarah, and Eunice.4
At this point, Edward’s family line descends not from John and Sarah’s oldest son, John, or their second eldest, Theophilus, but from their third child, Timothy, who was born in Salem in 1702. Known locally as “Deacon Pickering” for his involvement in Salem’s Trinitarian Church, Deacon Pickering was a man of firm conviction, moral character, and great piety. He was also industrious, enlarging the Pickering family estate, which he had inherited from his father, and through his frugality providing education to his nine children, including sending his two sons—John and Timothy—to Harvard College, the first in his family to do so.
Perhaps the most illustrious member of Edward Pickering’s ancestral line is his great grandfather, Col. Timothy Pickering, Deacon Pickering’s youngest son. As the youngest son, Col. Pickering inherited a much smaller share of the family estate, most of it going to his oldest sibling and brother John Pickering. As such, rather than spend his life on the family farm, or in business affairs of his own, Timothy joined the Fourth military company of Salem, rising to the level of captain in 1769. For the next few years, Captain Pickering served Salem and the surrounding county in several capacities: as city councilman, town clerk, justice of the peace, and register of deeds.
Never straying too far from his interest in military affairs, Timothy was appointed Colonel of the First Regiment of Essex County Militia in 1775, and, due to his law background, Adjutant-General of the United States Army two years later. A frequent visitor to General Washington’s headquarters, Col. Pickering soon became a favorite of the Continental Army’s high command. The association led to his appointment as one of three members of the Continental Board of War, and then to Quartermaster-General of the Army. Although he retained the rank of colonel, he was paid at the higher rate of brigadier-general. After the war, Col. Pickering found himself once again in the employment of the federal government: this time as Postmaster-General, a position he accepted in 1791. Four years later he was appointed Secretary of War, which included oversight over the Army, the Navy, and Indian Affairs, the latter of which he had had practical experience. During the same year, Col. Pickering became acting Secretary of State under President Washington.
After serving nine years in two different administrations—under President Washington and President Adams—Col. Pickering returned to private life. But that did not last long. In 1803, a year after he lost a bitter fight to represent the Federalist Party in the U.S. House of Representatives, the Massachusetts Legislature elected Col. Pickering to succeed retiring senator Dwight Foster. He was re-elected by popular vote two years later, whereupon he began a six-year term in the U.S. Senate. After his tenure in the Senate, Col. Pickering was elected by an overwhelming majority to represent Essex County North District in the Thirteenth U.S. Congress. Col. Pickering retired from public service in 1818 and for the next decade, before his death in 1829, lived in Salem, visiting the family farm in Wenham quite often. Like his ancestors before him, farming was in his blood, and living close to the land at the end of his life pleased him more than anything else. Col. Pickering married Rebecca White of Bristol, England, and raised seven children to adulthood—John, Timothy, Henry, Charles, William, George, and Octavius.
Of the seven children, Col. Pickering’s eldest son, John, Edward Pickering’s grandfather, concerns us the most. Not only does he represent the direct line of descent to Edward, but also he is the most fascinating, accomplished, and esteemed of his siblings. In many ways he is just like his father—industrious and ambitious. Born in Salem in 1777, John Pickering grew up under the watchful eye of his unmarried uncle, also named John, who occupied the family residence in Wenham north of Salem. After a childhood of public schooling and private tutors, John left for Cambridge where he studied law at Harvard. After graduating from Harvard in 1796, John moved to Philadelphia to practice law in the office of Edward Tilgman. But eight months later he found himself on a boat headed to Lisbon, Portugal, to fulfill the duties of Secretary of Legation. Two years later, he moved to London, where he became Secretary of Legation under Rufus King, the United States Minister to England.