Two years after he took charge of Calvary parish, Dr. Cheshire was married to Elizabeth Toole Parker, daughter of Theophilus Parker, his senior warden, and Mary Toole Parker. The next most important event in his life was the birth of his son and namesake, Joseph Blount, who was born on March 27, 1850. In the course of time Dr. and Mrs. Cheshire had five other children, Theophilus Parker, John, Elizabeth, Annie Gray, and Katherine Drane. John and Elizabeth, however, died in their second year. Joseph Blount was born in the house built many years before by his grandfather, Theophilus Parker. His father and mother had lived in it since their marriage and had come into its possession after the death of his grandfather. When Joseph was born his parents' household consisted of themselves, his grandmother, an aunt, and two cousins. With the subsequent births of his brothers and sisters his family was indeed a large one. The give and take of a large family probably played some part in the development of the tolerant and unselfish character which so distinguished him in manhood. Young Cheshire received his earliest education under the direction of his mother, who taught him reading, writing, and something about numbers. He did not attend a formal school until he was nine years old. However, he found himself to be "quite as far advanced in the knowledge of books as the most forward" of his companions. The school he first attended in Tarboro was taught by Rev. and Mrs. Owen. It was while attending this school that he and Richard Lewis met one another and formed a friendship which grew and continued for more than three-score years. In the fall of 1861 Cheshire entered the Tarboro Male Academy, whose sole teacher at that time was Mr. Frank S. Wilkinson, a graduate of the University of North Carolina. In this school Wilkinson took boys of every age, from beginners to those preparing for college. Cheshire later tells us that Wilkinson was devoted to the profession of teaching, laboring "faithfully to interest his pupils, and give them the best that he had himself." The school usually numbered between thirty and thirty-five boys, but when it included as many as forty, Wilkinson engaged an assistant. During Cheshire's attendance at the Academy, Mr. William Henry Johnston was employed as an assistant. He was also a graduate of the University and, as Cheshire says, "a very good scholar after the standards of the day." In this small school, which never boasted more than two teachers at any one time, Joseph Cheshire prepared himself for college.