The Henry Edmundson Letters contain nine letters, eight of which were written to Edmundson and one, the earliest of the letters, written by Edmundson in 1814 to General John Preston. The senders include William Ballard Preston; Francis H. Smith, superintendent of Virginia Military Institute (V.M.I.); Bernard Peyton; Isaac White; and Joseph Robert Woods. One letter, signed simply, "Wade," may indicate John Wade, one of the directors of the Lafayette and Ingles Ferry Turnpike.

The subjects of the letters range quite widely, but many have to do with financial matters, including various debts, loans, notes, and Bank of Virginia stock certificates. The letter to General Preston, dated 29 November 1814, refers to Edmundson's task of procuring hogs, perhaps to supply troops. Bernard Peyton's letter to Edmundson of 3 November 1823 is largely about "the progress of our unfortunate business with the Treasury," which refers to the aftermath of John Preston's tenure as Treasurer of Virginia and the disposition of property to satisfy his debt. Francis H. Smith writes to discuss a leave of absence at V.M.I. for Edmundson's son.