Caistor Grammar School is an endowed foundation school dating from the reign of Charles I. The Dissolution of the Monasteries in the reign of Henry VIII had destroyed the principal sources of education of the times, and the numerous schools endowed throughout England during the following reigns are evidence that public-spirited men recognised the need created and endeavoured to meet it. Among others was Francis Rawlinson, of South Kelsey, who died in 1630, bequeathing money to endow a school at Caistor, and William Hansard of Biscathorpe, who supplemented the original gift in 1634. The monies given were invested in the purchase of land at Cumberworth, and of the rectorial tithes of Bilsby, of which the governors are still lay impropriators.
The original trustees were Sir Edward Asycough of South Kelsey, Sir William Pelham of Brocklesby and Sir Christopher Wray Baron of Glentworth (Lord Chief Justice of England), and Johnathon Beltwick. Other trustees shouldered their responsibilities from time to time until 1885 when, under the Endowed Schools Act 1869, the Foundation was placed under an elective body of governors, the Vicar of Caistor being an ex-officio member. In 1908, the school was recognised by the Board of Education.
On 11 November 1931 it celebrated its tercentenary in the presence of Sir Arthur Quiller-Couch.
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