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 the history of Oakham School Army, Naval and Air Force contingents since 1910, and of the Boy Scouts. Most of the collection is made of photographs from the mid-20th century.

This sub-series relates to the history of the Cadets at Oakham School since 1910. The bulk of the collection is made of photographs of inspection throughout the 20th century.

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.

This file focusses on photographs of various Inspections of the Cadets and contingents, as well as group photographs of full contingents since the early 20th century.

A postcard of the inspection of the O.T.C. by Lord Roberts in 1912.

A photograph of the O.T.C. Guard of honour at Oakham Railway Station for the visit of Lord French in May 1917.

A photograph of the High Sheriff of Rutland, Major Herbert Whaley inspecting the C.C.F. cadets at the proclamation of Queen Elizabeth II in Market Place in 1952.

This sub-file contains photographs of C.C.F. cadets and camp in the 1950s.

A photograph of Oakham School cadets demonstrating artillery fire on Doncaster Close during an annual inspection in 1954.