In late February of 1866 young Cheshire left home for Hartford. An inexperienced boy, having traveled little beyond his section of the state, he now set out to enter a strange school among people with whom, less than a year ago, his people had been at war. Such a prospect would have filled an older heart with trepidation. He traveled as far as New York with a stranger who had been in Tarboro on business, and from thence he went alone to Hartford. Cheshire was allowed to enter the Freshman class with conditions only in Greek and Latin composition, which was a tribute to the work done under Mr. Wilkinson that fall. He learned upon arriving at school that he was the first man from the Confederate States to enter Trinity since the close of the war. He was treated kindly by his fellow students, and never complained of any hostility or unfriendliness on the part of the northern boys. His closest friends, however, were among a group of students from Maryland. Shortly after he entered college, his father wrote to President Kerfoot asking him to suggest someone on the faculty who would be willing to act as an advisor and friend to his son. Dr. Kerfoot proposed Rev. William W. Niles, Professor of Latin at Trinity, who gladly took Cheshire under his care. In time the two became fast friends. Professor Niles and his wife often entertained him and always made him feel at home in their house. Under Professor Niles' direction Cheshire was prepared for confirmation, and in May, 1866, he was confirmed in the college chapel. In later years he said of the Nileses: "I can never be sufficiently grateful to Professor Niles and his good wife.... I enjoyed from that time—from my Freshman days in college to the end of their lives, the friendship and confidence of these most admirable people."[3]