Family papers in this collection are essentially limited to seven letters, eighteen photographic images, and one of Judge Shepherd's visiting cards. The letters range in date from 1864 to 1866. All were written to Shepherd's younger sister, Frances S. (1848-1938). Six of them were written by Shepherd and one was written by their older sister Elizabeth. All were written for the purpose of keeping the three orphaned teenagers in touch with one another during the troubled period of the war and the months immediately following it. Such news as they contain relates to kinsmen and friends. Shepherd's letter of September 4, 1865, includes comments on the post-war commercial growth of Wilson, N.C., a brisk little place. Elizabeth's letter of April 20, 1866, describes changes at Forest Hill where she has returned to her teaching duties. A visiting card of Shepherd's is filed in the same folder as the family correspondence. The family photographic images are described separately at the conclusion of this finding aid.

Business papers include correspondence, bills of sale, deeds, assignments, and lawsuit papers all dating from 1873 and 1874 when Shepherd was in legal practice with Thomas Sparrow at Washington, N.C. Of the deeds and land papers in the collection, most have sequential numbers assigned to them, and though they range in date from 1806 to 1857, they appear to relate to one another in an unspecified land dispute in which Shepherd's firm acted for one of the disputants. There is, too, a single document relating to a lawsuit in Florida concerning a mill near Pensacola owned by a Mr. Fowle of Washington, N.C., whose interests were represented by a Florida firm as well as by the firm of Sparrow and Shepherd.

Two files of papers concern the settlement of debts and legal fees owing in 1874 from estates of decedents: William L. Kennedy of Beaufort and Greene counties, and Thomas D. Swindell of Hyde County. Yet another file of papers relates to a lawsuit involving the schooner John Griffiths following its return to Washington in 1873 from a voyage to the West Indian island of St. Martin. Legal action was brought against the vessel by various creditors, by one of its shippers, and by its mate and seamen for back wages. The file includes a bill of lading at St. Martin, subpoenas, assignments, bills of sale, and record of the vessel's enrollment under the federal act regulating coastal trade.

Three files of papers relate to properties, or interest in properties, owned by Isaiah Respess, businessman and former mayor of Washington and state representative from Beaufort County. The first file contains an 1874 assignment by Respess to his attorneys-at-law, Sparrow and Shepherd, of a quarter interest in a French spoliation claim originally belonging to Joseph B. Hinton for a vessel seized on the high seas by the French sometime prior to the year 1801. Included in the file is a printed copy of an 1849 U.S. Senate document on the subject of pre-1801 French spoliation claims and an 1872 leaflet on the same subject by a Washington, D.C., attorney specializing in such claims, James H. Causten. This same 1874 deed of assignment includes a second assignment from and to the same parties and conveys quarter interest in a legacy under the last will and testament of Hull Anderson of Liberia, a free man of color, to Joseph B. Hinton.

The second file relating to Respess property concerns a steam sawmill located at the southeastern edge of Washington that Respess had purchased from the lumber magnate Benjamin F. Hanks in 1859. Despite the fact that Respess had been arrested as a Unionist sympathizer and sent to Richmond where he was imprisoned, tried for treason, and released by the C.S.A. government, his sawmill was destroyed by U.S. military forces during the Civil War. Consequently Respess lodged a claim with the Southern Claims Commission for the value of the mill. The file contains an 1874 assignment from Respess to Sparrow and Shepherd of a quarter interest in the pending claim; an 1867 affidavit by Benjamin F. Hanks (the younger) describing and assessing the value of the steam sawmill and identifying Respess as a thorough going Union man; an 1873 letter from the Washington, D.C., attorney, J. M. Cutts, regarding the claim; an example of a claim that had been allowed by Congress but disallowed by the president for stipulated reasons; and an 1863 receipt to Respess from a federal quartermaster for corn meal taken for use of the U.S. government.

The third file relating to Respess property concerns guano deposits on Roncador Island in the Caribbean in which he held half-interest. The file contains an 1869 letter to Respess asking for the specific location of the island and deposits so that shipping arrangements might be made; an 1874 deed of assignment of a quarter interest in the deposits from Respess to James E. Shepherd and Mary B. Tayloe; and a draft of an inquiry from Shepherd to the U.S. Secretary of State about the legal status of the original claim to the deposits.

There are five miscellaneous documents in the collection, two of which have a Shepherd connection: (1) an 1870 insurance policy on the life of Shepherd; (2) a booklet to be used by Democratic Party sub-district committeemen in getting out the vote in the 1876 presidential election. Two of the items have no discernible connection to Shepherd: (1) an 1872 invitation to a Hop at the National Hotel in Raleigh written by John on letterhead of the Raleigh drug firm, Pescud, Lee & Co., to bear Belle; (2) a brief 1884 biographical statement, or vitae, of James Fair Latimer (1845-1892), professor of metaphysics at Davidson College in 1872, and professor of ecclesiastical history and polity at Union Theological Seminary from 1884 to 1892. The fifth miscellaneous item in the collection is a small duodecimo edition of , compiled by the Rev. T. Merritt from the works of John Wesley and published at New York in 1832. The volume was owned by Judge Shepherd's mother, Ann Eliza (Browne) Shepherd and was autographed by her in 1835. This volume is filed in the first box of materials along with the family letters.

Family photographs take the form of daguerreotypes, tintypes, cartes-de-visite, ambrotypes, and mounted and candid paper photographs, and include images of members of the Shepherd and Browne families.