The papers consist of two series: Correspondence, 1818–1824, 1836, and Estate Materials, 1843–1865, and n.d. Estate Materials is further divided into two subseries: Estate Correspondence, 1843–1865, and Financial Records, 1843–1845 and n.d. The Correspondence series includes a series of letters from Benjamin Franklin Bosworth’s school days at Lenox Academy in upstate New York and Union College. The materials are modest, but they do shed light into the life of a student at the beginning of the nineteenth century. Of particular interest is Bosworth's description of housing for students during his schooling. The Estate materials offer a view of the financial details of a small mercantile operation of the mid-nineteenth century in McHenry, Illinois. This material includes a comprehensive list of Bosworth's assets and debts, invoices, notes of credit, and correspondence documenting the legal procedures associated with the settlement of an estate.

Series I. Correspondence, 1818-1824, 1836

This series documents Bosworth's life as a student at Lenox Academy and Union College. The bulk of the correspondence is with his parents and brother, although there is one letter of introduction from Andrew Yates of Union College and one promissory note of 1824.

Series II. Estate Materials, 1843-1865, n.d.

This series, divided into two subseries, documents the handling of Benjamin Franklin Bosworth's estate by his brother, Increase Child Bosworth. It includes Estate Correspondence and Financial Records.

Subseries 1. Estate Correspondence, 1843-1865

This subseries includes letters pertaining to the settling of estate debts and to the legal handling of Benjamin Franklin Bosworth's estate by B. S. Morris of Chicago. The correspondence documents the major sites of BFB's business: Chicago, Albany, Buffalo, and McHenry, Illinois.

Subseries 2. Financial Records, 1843-1845, n. d.

This subseries includes three types of materials: the comprehensive record of the estate account, the records of debts, and receipts from the estate.