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.