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A collection which charts the various societies and activities available to pupils at Oakham School. Documents include photographic records and correspondence for different societies. Topics include chess, CCF/OTC, scouts, Duke of Edinburgh Award, Oligoi , Exploratory Society, and trips and expeditions.

The multiple series contain administrative documents for the various societies and certain series, such as Duke of Edinburgh Award and CCF/OTC have excellent photographic record of formal or informal events.

There is a particularly detailed series on Chess and the event of Gary Kasparov's visit to the school.

There is a good collection of shooting medals and trophies, kindly donated by Henry Blagg.

An album containing photographs of the O.T.C. and C.C.F. at Oakham School. Some names are written next to the corresponding photographs. Topics include inspections, First World War Cuttings, Jubilee Parades, Armistice Day, Drums, Proclamation of King George VI, demonstrations of arms, letters and newspaper clippings.