The will of Reuben Shephard was dated 15 March 1820. To beloved wife Betsey. To my youngest daughter Mary Gilby Shephard. My daughter Patsey Shephard. My daughter Frances Boughton. James Greenwood and Thomas Greenwood to be executors. Signed Reuben his x mark Shephard. Witnesses: Twyman Greenwood, John St. John, Thomas his x mark Collins. Proved 17 April 1820. [Essex County, Virginia, Will Book 19, pages 96–97.]

On 17 April 1820, James Greenwood, Thomas Greenwood, Twyman Greenwood, John Cauthorn, John St. John, and Thomas Collins were bound in the penalty of $6,500 for James Greenwood’s and Thomas Greenwood’s administration with the will annexed of the estate of Reuben Shepard. [Essex County, Virginia, Will Book 19, page 97.]

On 15 May 1820, an inventory and appraisal of the estate of Reuben Shepherd, made by A. S. Boughton, Edmd. Covington, and Zachariah Shackleford, was returned to court. [Essex County, Virginia, Will Book 19, pages 100–102.]

The estate of Reuben Shepherd in account with James and Thomas Greenwood, adminstrators, for 1820 and 1821 was settled on 16 July 1821 by Anthony Haynes, Kemp Gatewood, and John Saddler. [Essex County, Virginia, Will Book 19, pages 233–234.]