This collection contains 60 letters Henry Edmond Gregory wrote to his mother, Elizabeth Gregory, and 3 he wrote to his father, Rear Admiral Francis H. Gregory, between 1858 and 1861. He wrote 11 letters from New Haven, Connecticut, and Boston, Massachusetts (August 22, 1858-December 11, 1858); 24 letters while working in a foundry in Charlestown, Massachusetts (January 29, 1859-July 24, 1859); 23 while living in Niobrara, Nebraska (January 8, 1861-July 8, 1861); and 5 from cities along the East Coast (September 18, 1861-October 30, 1861).
Henry wrote his first 11 letters from New Haven, Connecticut; Charlestown, Massachusetts; and the U.S. Navy Yard, Boston, between August 22, 1858, and December 11, 1858, with news for his mother about his siblings and comments regarding the navy. He frequently referred to a friend named "Mac," who joined a ship's crew during the period. After January 29, 1859, he wrote his parents weekly from Charlestown, Massachusetts, where he worked in a "government foundry." He described his work and complained of the loud noise generated by the shop's machinery, and often mentioned social events and leisure activities. In one letter to his father, he inquired about personnel changes in the navy (March 7, 1859).
Between January 8, 1861, and July 8, 1861, Gregory wrote 22 letters to his mother and 2 to his father, concerning his life in Niobrara, Nebraska Territory. He frequently wrote of his brother John, who lived nearby, and of his own interactions with local Ponca Indians, including visits to a local trading post. He commented on several other aspects of life in the Nebraska Territory, such as the small population, the local residents' desire to build a church, and his work running a store. In his letter of January 24, 1861, and in many letters after April 1861, he referred to the buildup to, and outbreak of, the Civil War, including the local reaction and President Lincoln's call for soldiers. By September 1861, he had returned to Charlestown, and his last letters reflect his ambition to receive an appointment as assistant paymaster. He wrote these letters while traveling along the eastern seaboard with his father.