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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 monograph written by Brian Needham on the Oakham School Exploration Society and the overseas expeditions from 1979 to 2012.

A bound copy of several Old Oakhamian Magazines from 1994 to 2002.

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.

The group journal of Oakham School Exploration Society's expedition to Namibia in 1998. The diary entries were hand-written by pupils.

The Old Oakhamian Magazine, published in March 1997. Contents: World Record Holders; Jack Barber; All Your Yesterdays; Raleigh International's Chile 96A Expedition; O.O. News; O.S. Exploration Society; Obituaries; O.O. Annual Dinner; Announcements; Sports; Art Exhibition; Oxbridge Success.

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.