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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.

This series relates to events organised by Oakham School Biology Society and the Medical Society.

A poster advertising an Oakham School Medical Society event with Old Oakhamians discussing Medicine careers held in the Wilson Auditorium on 23 March 2022.

This series relates to the history of the Scholars Society at Oakham School.

This series relates to the history of Oakham School Film Society.

A certificate from the Diana Princess of Wales Memorial Award for Young People in recognition of students who have made a real difference to tackling bullying in their school communities awarded to Jerwoods Film Activity in the academic year 2005-2006.

This sub-series contains various journals and reports of expeditions organised by Oakham School Exploration Society in the 1970s and 1990s.

This series relates to the history of Oakham School Exploration Society since its inception in Spring term 1978 until 1998. Most of the collection is made of expedition diaries and reports.

This sub-series relates to various administrative documents of the Exploration Society, such as the Society's diary and invitations to lectures. The sub-series spans from 1978 to 1998.

A book recording events and trips of the Oakham School Exploration Society since its inception in Spring term 1978. A badge of the society is glued on the cover.