In 1584 Uppingham School was founded with a hospital, or almshouse. The original 1584 Schoolroom in Uppingham churchyard is still owned by the school and is a Grade 1 listed building. The original hospital building is now incorporated in the School Library. The first recorded Uppingham schoolboy was Henry Ferne from York, who was Chaplain to Charles 1. Academic work is central to Uppingham’s goal of nurturing the whole person. Pupils are encouraged to develop intellectual curiosity, to question received wisdoms, to think deeply and engage with serious subjects across a range of academic disciplines, and to articulate their own thoughts. Uppingham has the greatest area of playing fields of any school in England, in three separate areas on different sides of the town: the Leicester to the West, the Middle to the South, and the Upper to the East.
Uppingham is considered one of Britain's best schools for music, and the school's music facilities have been improved considerably recently. The school houses two large three-manual pipe organs, in the Memorial Hall and the Chapel; the latter was substantially rebuilt in the summer of 2007 by Nicholson Organs of Malvern. A completely new Choir division is now situated high on the South wall, and a new console and action has been installed, along with new pipework. The organ is notable for its smooth Harrison tone and rare two independent sets of Swell shutters – one opening westwards into the nave extension and one southwards across the repositioned choir stalls. Uppingham has one of the largest private theatres in the country, in a building based on the original Leipzig Gewandhouse. An extension to the main theatre houses a Drama studio to be used for the teaching of Theatre Studies as well as for performances of smaller productions. There is also a large workshop to provide storage and workspace for technical equipment.
Two years before entry, at age 11 (when pupils are in Year 7), all registered pupils are invited to a test and interview day to win a place that is conditional on passing another test during the following academic year, prior to entry thereafter.
The Uppingham pre-tests comprise papers in Maths and English, both being 30 minutes long. Prospective pupils will also interview for 10 to 15 minutes with two members of staff, an interview that is supported by a reference from their prep or junior school. Past papers are not available.
For many any place won will be conditional on Common Entrance where the School seeks a 55% average pass mark. Others will fulfil this condition by sitting academic scholarship examinations. (Uppingham uses the CASE scholarship papers set by ISEB.) For pupils from schools that do not offer CE, candidates fulfil their offer by sitting the Uppingham Non Common Entrance test which is made up of two 40-minute tests in Maths and English and typically takes place by individual arrangement in February or March prior to entry in September. The Non Common Entrance Test usually takes place at Uppingham and is accompanied by an interview with the Director of Studies and an updated reference from the current school.