This collection consists primarily of letters written by Herbert Babcock to his stepmother Prudence, when he was a student at a secondary school in Adams, New York. In his 10 letters, which cover the winter term from 1866-1867, he discussed his health, lessons, leisure activities, and reactions to family news from home; he often admitted to suffering from homesickness, though he enjoyed living with his aunt and uncle on their farm. Herbert gave details of his lessons, including the subjects of his written compositions and the structures of different classes. He also noted the strictness of his teachers and mentioned a rule against "wink[ing] to a girl in the classes" (December 22, 1866). Despite his ongoing difficulties with mathematics, Herbert generally enjoyed his studies and, after realizing the current term was likely to be his last, vowed to get the most out of his education. Herbert wrote about his life in northern New York, the school's military drill exercises, a baseball club formed by several students, and his attendance at a local party. The collection also includes a letter from his Aunt Lovina to her sister, in which she discussed her recent poor health and the effects of the draft (July 26, 1863), and pieces of embroidered ribbon.