Majority of the letters are to Hugh Carrington Grigsby from family and friends, but two undated letters are to "Mrs. Grigsby" from H. C. Nowlin in Richmond, Virginia about buying items for Mrs. Grigsby, and health problems. Hugh Carrington Grigsby attended "The Cluster School" at "Blackwalnut P. O." in Halifax, Virginia in 1871 and 1872. 1871 January 8 letter from "Johnny" at Hampden-Sidney College talks about how wonderful college life is. Letters from both his mother and father are full of advice and some criticisms. His father, Hugh Blair Grigsby, often tells Hugh Carrington Grigsby, with many examples, that the work he does now will enable him to be successful later. Clem D. Lewis writes twice in late 1871 about his troubles with the whooping cough and recent and future parties. In 1872, Hugh Blair Grigsby writes about the death of cousin Clem C. Read "who was named after Grandfather." Hugh Blair Grigsby tells Hugh Carrington Grigsby "Father cannot tell you how much his heart is set upon you and how anxiously he wishes you to be what you can so easily become if you are true to yourself." In 1872, Hugh Carrington attends Hampden-Sidney College. In 1873, his sophomore year, his father is writing with suggestions about his difficulty in mathmatics and "as you stand in the Sophomore year, so you stand for the rest of your course. I wish you to be a scholar for many reasons, and not the least is that your future fortunes depend on your success. You will have to make your own way in the world; and the more accomplished you are in your studies, the greater the probability of success." 1874 May 4, his Father writes, "Both my health and your mother's is frail, and we look to you as our support in our declining years, and we are solicitious that your conduct will entitle you to the esteem of all men and women with you associate." 1890 October 26, letter from William T. Grigsby, Union City, Tennessee, to Mrs Grigsby, Relict of Honorable Hugh B. Grigsby, requesting a photograph of Hugh Blair Grigsby. An undated letter from Hugh Carrington Grigsby relates a story he heard from a "youth" about "cogitations upon the prospect of entering college".