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Gillingham School is a comprehensive school situated in Gillingham in North Dorset. Gillingham Grammar School can trace its foundation back to 1516, making it probably the oldest surviving school in Dorset. It was founded as a Free School, paid for out of the proceeds of land gifted to the school by several local landowners, and was managed by twelve trustees or Feoffees. Evidence exists to prove that the Gillingham Free School persisted without a break until the present day although the format has metamorphosed to a Grammar school and then to its present Comprehensive status. Among its distinguished early pupils was Edward Hyde, who became Earl of Clarendon, and Lord High Chancellor of England 1661 - 1667. Edward Frampton was the headmaster in 1648 and he became Bishop of Gloucester in 1680.

Over the years the school further prospered, and in 1916 girls were admitted for the first time. It was in 1926 that the school came under the control of the Dorset County Council who agreed to pay the staff salaries and provide grants for most education needs. In 1940 a County "Modern School" for the less academically able was built in a field next to the Grammar School and in 1959 the two schools combined into a Comprehensive School. Over the years and particularly in recent times the buildings were modernised and eventually all were replaced. The present school now has a roll of over 1500 pupils and an enviable reputation for high achievement.