We shall probably never know who was the first boarder at the school; whether it was Master West, of Alscot Park, who lived with the Rev Joseph Greene during his headmastership and concerning whom we have such a wealth of correspondence between the headmaster and the Hon James West covering the years 1749 to 1764, or whether others had previously been accommodated in the school in a similar way.
The report of the Schools Inquiry Commission of 1867 makes it clear that there were no boarders at the school at that time, but the new scheme of 1876 which followed as a result of that inquiry provided that in future the school should have boarders if the governors thought fit, and brought this development a step nearer by providing an official residence for the headmaster in 1877. This house, opposite New Place Gardens in Chapel Lane, had been used as a private school by Mr Warrilow since he had vacated his previous room, which was the southern half of Big School, in 1845, and it was now enlarged and became School House. Soon after this the headmaster encountered opposition in the form of a landlady in Old Town who advertised rooms for boys in her house, presumably at a lower figure than the headmaster's, but although the governors took a serious view of this development they felt that they could do no more than set up a visiting committee to ensure that her accommodation was satisfactory.
The idea of boarders was not quickly accepted, and even a year after the Rev R S de C Laffan had come (admittedly a year of great trade depression) the school could still muster no more than two official boarders. Then the tide began to turn in its favour, the following year there were six, then eleven, and by 1892 there were twenty boarders and six resident assistant masters in School House, and the headmaster had suggested the purchase of the Old Vicarage to make room for more. Then the tide began to ebb again, and in his last report to the governors in 1895 Laffan had to admit with regret a decrease, particularly in the number of boarders and attributable to a serious and general depression of incomes; and to make matters worse, when he went to Cheltenham College as headmaster a good number of the boarders followed him there.
The Rev E J W Houghton tackled his work courageously from a bad start, and in spite of a necessary increase in boarding fees the numbers slowly began to mount again. A new study block was built at the back of School House in 1888 when every dormitory was full, and the following year the headmaster built the new dining hall at his own expense and was able to report that there were now thirty-three boarders out of a total strength of ninety-one in the school.
When he left the school in 1902 Houghton took a number of the boarders with him to Canterbury (this seems to have been a feature of headmasters' movements in those days) and so passed on to the Rev Cornwell Robertson the problem that he had himself inherited. Even so, the boarding side soon gained in popularity again, the old dining hall was fitted up as a reading and recreation room and became the headquarters of the school Debating, Scientific and Photographic Societies and the Chess Club, and eyes were again turned towards the Old Vicarage; by 1904 the School House was full once more. Then again, slowly, the boarders drifted away, and when the Rev A C Knight came in 1914 there were practically none at all,
From The Story of Shakespeare's School 1854-1953 by Leslie Watkins
(Stratford-upon-Avon: Herald Press and Edward Fox & Sons, 1953)