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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.

A booklet for the Bronze Qualifying Expedition in the Cheviot Hills in 2009. Contents: Instructions for staff and students; Campsites and contact details; Student photos; Medical details; Risk Assessment; Map routes; Expense form.

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

A book containing Oakham School Exploration Society's report on the Svalbard expedition in 1979. Contents: The Expedition Concept, Aims, Area, Members and Budget; Fundraising; Approval; Food; Transport; The Expedition Diary; The Advance Parties; The Botanical Programme; The Ornithological Programme; The Physiological Programme; The Snow and Ice Programme; The Adventure Programme; Medical Report; The Final Stage; The Rear Party; Communications; Insurance; Lecture and Reception; Individual Contributions.

A booklet containing Oakham School Exploration Society's report on the Zambia & Zimbabwe expedition in 1995. Contents: Expedition Members; Maps; Diary; Lists of Mammals and Birds.

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 programme for the visit of His Royal Highness The Duke of Edinburgh to Oakham School on 28 November 2000. Two double-pages A and B.

This contains photographs of the visit of HRH The Duke of Edinburgh and the celebration of the 1000th Gold Awards being awarded at Oakham School.

This sub-series contains documents relating to the organisation of various Duke of Edinburgh expeditions, including pupil lists, risk assessments and maps.