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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 collection of photographs and art work relating to the whole School Campus, in particular aerial photographs from 1937 of the School and the town, and a file of individual photographs of buildings around the campus. The oldest items in this sub-series date back to the 19th century.

A poster of photographs of the school in 1977. Including Lincoln house, the Science block, the badminton courts in the Sports Hall, a girls' dorm, the Ashburton Dining hall and the indoors swimming pool.

A report from Rev John Darrall to be published in the Oakhamian Magazine on the charity events organised during the Summer term 1991, including the St Valentine's Day disco, a Non-Uniform Day, concerts, Laundry Day and sponsored sporting challenges. Three pages A to C.

This sub-series is related to 'Crime Day', a special event where Lower School pupils are invited to activities and puzzle solving to explore the school campus.

A leaflet advertising Crime Day at Oakham School for Lower School pupils on Sunday 4 November 2018.

A leaflet advertising Crime Day at Oakham School for Lower School pupils on Sunday 17 November 2019.

Order of service for a Saturday Service for Hodges House in Jerwoods on 5 October 2019.

This file contains invitation sent out to Parents and Guardians to attend Carol Services at the School Chapel.

An invitation to the Lower School Carol by Candlelight service in the School Chapel on 10 December 2017.