Series III. Fifth Generation Business and Personal Papers, 1686-1887, contain the papers of John(5) Pickering (1740-1811) and his younger brother Timothy Pickering (1745-1829). The papers of John(5) Pickering reflect his years in public service at the state and local levels. Business papers and receipts pertain to the Massachusetts House of Representatives, Essex Country Registry of Deeds, Essex County Bar, and the Salem town treasury. Of particular interest is a journal of the committee that drafted the Massachusetts constitution in 1777. There is also a diary on gardening, and a deed for land in Danvers.

A large portion of the Pickering Family Papers belong to Timothy Pickering (1745-1829). These include business and legal papers, military papers, business and personal correspondence, missions to Indians, agricultural journals, historical notebooks, account books, printed materials, and newspaper clippings. Business papers and correspondence are grouped together because many are notes, drafts of letters, or copies of letters, some written in Timothy's hand and others copied by scribes. Included is correspondence with George Washington, Alexander Hamilton, and John Adams, among others.

Many of the early papers focus on the Essex County Militia. Additional papers pertain to Colonel Timothy Pickering's years in the Continental Army, where he was appointed Adjuvant General in 1777, served on the Board of War (from 1777) and became Quartermaster General in 1780. Following his resignation from the Army in 1783, many papers concern his business partnership with Samuel Hodgdon. In 1785, topics covered in the papers include his dealings in land speculation in Luzerne County, Pennsylvania. Included are depositions collected after Timothy was abducted by some disgruntled settlers from Connecticut and held hostage for nineteen days in 1788.

Papers in Boxes 3 and 4 span Timothy Pickering's years in the government, first as Postmaster General (1791-1795), briefly as Secretary of War (1795), and then as Secretary of State (1795-1800). His letters as Secretary of State reflect his increasing dissatisfaction with the French government and his subsequent dismissal from the government in May 1800. A continuing worry of Pickering's was providing for his family, and several letters pertain to disposal of his lands in Pennsylvania. Pickering returned to Massachusetts in 1801; he continued to write on the early days of the Republic, and to engage in political controversy. Subjects discussed in these papers include his opposition to Thomas Jefferson's doctrines, and later opposition to the War of 1812, when he went so far as to propose secession of the New England states. Also included in Box 4 are invitations to Timothy and his wife Rebecca, mostly received during his years in government.

When letters between John Adams and William Cunningham were published in 1823, Pickering wrote a rebuttal of many of the statements made in them. Drafts of his rebuttal are in Box 4, Folder 8 and Box 5, Folders 1-3. Also in Box 5 are miscellaneous business notes, memoranda, agricultural notes, pamphlets, speeches, and addresses on Indian affairs and political matters, and documents concerning the First Church in Salem. Box 6 contains assorted legal papers, including powers of attorney, summons, warrants and complaints, certificates, deeds, indentures, and mortgages and wills. Some of these papers precede Pickering's days as a lawyer in Salem, but they have been retained with the rest of the Pickering collection. Also in Box 6 are papers and correspondence related to Timothy Pickering's later years and death in 1829.

Colonel Timothy wrote frequently to his wife Rebecca during their long separations. Box 7 contains typewritten transcriptions of over 600 letters to her spanning the years 1775 to 1827. Some letters include glimpses of military or business affairs, but many are devoted to personal matters, such as relocating the family, the health of the children, or Pickering's desire to return to New England and settle as a farmer. Timothy also wrote frequently to his brother John (B8 F1) and to his children. There are about 270 typewritten transcriptions of letters to his eldest son John, who was his closest confidant (B8 F2-F4). In early letters Pickering counsels his son with regard to his education and study abroad. Later letters discuss American foreign policy and offer candid opinions of George Washington (March 3, 1810), John Adams, Thomas Jefferson, James Madison, Aaron Burr, and Elbridge Gerry among others. Also present are (handwritten) letters to sons John, Timothy, Charles, George, and Octavius and letters to twin daughters Elizabeth Dorsey and Mary Nichols and their husbands. Other personal correspondence includes drafts of letters to family members, letters to or from Rebecca Pickering, and papers concerning Rebecca (White) Pickering's family. The White family folder contains the marriage certificate (1757) of Rebecca Pickering's parents, Benjamin White and Elizabeth Miller, and letters to Rebecca and Timothy from Rebecca's sister Elizabeth, who did not come to America until 1785.

Business records (B9) include inventories and accounts, bills and receipts, a cashbook and three bankbooks. Many records pertain to the brigantine Hope or to other vessels including the cutter Royal George, ship Benjamin, or brigantine Nymph. Other records relate to Pickering's years as Quartermaster General, including the mustering out of officers from 1780 to 1783. There are also accounts spanning the years while Pickering was in business with Samuel Hodgdon and later while he was speculating in land in Pennsylvania. An oversize ledger itemizes expenses in Susquehanna County, Pennsylvania, from 1787 to 1791 (Cabinet 2 Drawer 9). One cashbook covers the years 1780 to 1800 in detail. Another cashbook pertains to Pennsylvania (1784-1803) and includes a record of lands surveyed in Ohio County, Virginia, in 1784. One bankbook dates from Pickering's time as Secretary of State, (1799), while two others are from Boston (1808-1809 and 1826).

In Box 10 are assorted journals, memoranda books, and maps. Four journals (F1) describe Pickering's experiences in the Continental Army from 1776-1777 and 1780-1781, and another (F2) describes a trip along the Susquehanna River in Pennsylvania (1786). One memorandum book (F3) summarizes the family genealogy; the next folder (F4) contains a copy of this book, including the additions by his son Octavius Pickering and granddaughter Mary Orne Pickering. Also present is a shorthand manuscript book (1769), a copybook pertaining to the First Church in Salem (1824), a missionary journal by William Torrey (1823-1824), and miscellaneous maps. Pickering's agricultural journals (B10-11) reflect his lifelong interest in agriculture. Topics in the journals primarily concern animal husbandry and gardening. Others contain extracts of published works on similar subjects of interest to Pickering and include observations made by European agriculturalists. Finally there are printed materials from Pickering's years as Secretary of State or member of Congress (B12 F1), his years in Massachusetts (F2), as well as other printed items. Newspaper articles in F6 pertain directly to Pickering, while those in F7 pertain largely to his broad interests in national and international affairs.