Cheshire came to know a number of people in the neighborhood of the school who helped to make his life at St. Clement's more interesting and pleasant. He spent a good many week-ends in Baltimore with some of his Trinity friends. When his oldest and best friend, Richard Lewis, came to Baltimore to study medicine in the fall of 1870, his visits became more frequent. On the whole, his life at St. Clement's was happy, and the experience he gained, worth while. He never, however, became fond of teaching, but he enjoyed his students and took a warm personal interest in them. After two years at St. Clement's he decided to abandon teaching for the law profession, which he thought would be more congenial to his tastes.

When Cheshire returned to North Carolina in June, 1871, he went with his family to Hillsboro to spend the summer. Here he began the study of law under the eminent lawyer, William K. Ruffin, son of Chief Justice Thomas Ruffin, who coached law students since he was too crippled to do much active practice. Ruffin was a "devotee" of the common law and always gave his students a thorough drilling in it. He made Cheshire devote almost all the summer to the study of Second Blackstone and Cruise's Real Property. When he left Hillsboro in September, Ruffin made him promise that he would secure an old folio edition of Coke's Commentaries on Littleton and read it carefully. Some time later Cheshire bought a copy of this work in Baltimore and read it from cover to cover as he had promised. He once remarked that he believed he was the last man in North Carolina to have completely read the old folio edition. Cheshire found Mr. William Ruffin "a most interesting man as well as a stimulating and helpful teacher."[4]

Upon returning to Tarboro Cheshire continued his study of law, now in the office of Howard and Perry. In this office he "read law," for he says that Judge George Howard would not agree to give him any instruction. Cheshire, however, maintained that he learned much law from Judge Howard, and "a good deal of sound practical wisdom."

After his summer's work under William Ruffin and some three months' study in Judge Howard's office, Cheshire was ready to try for his license. On January 1, 1872, he went to Raleigh to be examined by the Supreme Court Justices. It was an oral test and, in Cheshire's own words, was "a very slight and superficial examination" in comparison with those given today. The day after the examination he was informed that he had passed and was granted his license.

Shortly afterwards George G. Hooper, a Trinity College friend, wrote Cheshire to come to Baltimore and join him in a law partnership. He did not particularly care to leave North Carolina, but he feared if he remained he might be a burden on his father while establishing himself. He accordingly accepted Hooper's offer, and the two men formed a partnership under the firm name of Hooper and Cheshire. Hooper agreed to pay him a salary for the first year, at the end of which time they would make a new agreement.

Cheshire had not been in the office long before he learned that Hooper had "little real law practice." His work was almost entirely confined to drawing up conveyances and examining land titles. After some fifteen months of this sort of work, Cheshire realized there was little future for him in such a partnership. It was, therefore, with much pleasure that he received, in May, 1873, a letter from his friend, John L. Bridgers, Jr., asking him to return to Tarboro and join him and his father, Colonel John L. Bridgers, in the practice of law. Cheshire readily accepted this proposal, and the following month came back to North Carolina where he was to make his home for the remainder of his life.

Cheshire was happy to be living in Tarboro once again with his family and among his old friends. Thus was formed the firm of Bridgers, Cheshire, and Bridgers. This connection continued until January, 1875, at which time Cheshire was offered the position of secretary and treasurer of the Pamlico Banking and Insurance Company, a corporation organized to solicit fire insurance. He accepted the offer because it gave him an office and a small salary and did not interfere with his law practice. The company's business was not extensive, and required only a few hours of his time each day. While holding this position he was also treasurer of the Tarboro Building and Loan Association. Again this office demanded little of his time, merely requiring that he receive the money from the secretary weekly and pay it out upon his order.

Cheshire continued the practice of law until the early part of 1878. In summing up his work at the bar, he observed: "I made a living and saved a few hundred dollars. I had no very interesting or important cases, so far as I recall."[5] During his last year of practice, however, he made a little over fifteen hundred dollars, which, for a young lawyer of that period, was doing quite well.

Since leaving St. Clement's Hall in June, 1871, Cheshire had not by any means devoted all of his time and thought to the study and practice of law. He accomplished a great deal more in the summer of 1871 than the study of common law under Mr. William K. Ruffin. It was then that he renewed his acquaintance with his cousin, Miss Annie Huske Webb, who lived in Hillsboro. He had seen this cousin but little since her visit to Tarboro in December, 1865. He always remembered the first time he saw her upon her arrival in Tarboro for that visit and described the meeting thus: "When I looked at her, as she came in out of the rain, and lifted the veil from her face, I thought her the most beautiful person I had ever seen. I think that first impression was never effaced."[6]

In the course of the summer spent in Hillsboro Cheshire saw a good deal of his cousin. It was not long before he realized that he was in love with her. While not possessing a particularly romantic nature, Cheshire was a man of deep emotions and fine sentiments. During his courtship of Miss Webb he composed for her this little poem: