The school is noted for its distinctive collegiate and pastoral structure, a varied sporting, outdoor education and cultural co-curricular programme and participation in the life of the local community.

Pupils attend their house for morning and afternoon registration, to play games throughout the day, and for the majority of the administration which governs their time at the school.

The authenticity of this claim is rightly questioned: shortly after Incent's death, a complaint was made to the king "by some evill persons that the Deane had laid to the Schoole more revenues than his licence [£40 annually] did permitt him."

However, there had been no formal incorporation of the school, and records suggest that Incent had spent much time since the opening preparing, but not realising, legal protection.

Richard Reeve, the first headmaster, held strict Protestant views, and was dismissed by the Bishop of Lincoln, acting upon Queen Mary's instructions, in 1555.

By 1616, some years after Saltmarsh's death, it was written Scholae Ludimagister cum 33 annos eidem praefuisset amplam pecuniam testamento suo moriens legavit reficiendis his aedibus which Williams translates: "William Saltmarsh, third Headmaster of this School, after presiding over it for 33 years, on his deathbed bequeathed a sum of money sufficient for the repair of this building."

It is uncertain why the building (by which it is meant Old Hall) had fallen into disrepair under an otherwise successful headmaster, but through his donation Saltmarsh had decisively added himself to Berkhamsted's list of benefactors.

His period in the office probably witnessed greater stability in the school than in his personal life – he was married four times – and there was praise for his leadership, a former pupil recording "much reverence and affect" for Hunt.

It also appears that he took as active a part in the life of Berkhamsted as had become and remains a tradition, serving as overseer for the poor and bailiff as well as contributing to church funds.

It is some indication of the extent of Berkhamsted's degeneration under Fossan that his successor, Edmund Newboult, was recommended by the Bishop of Hereford as "of parts sufficient for so mean a school," an endorsement described as "comically unenthusiastic".

During his 17 years of office, Newboult does appear to have provided a solid educational environment at Berkhamsted, at least relatively speaking, something continued under his successor, Thomas Wren.

Nonetheless, the three inspections[10] carried out during the three years found no cause for concern, and in their record is revealed the first reference to curriculum content, the boys having been examined on Ovid's Metamorphoses.

On Theed's death in 1734, his succession, still the jurisdiction of the sovereign, brought Price to the headmastership, despite his not having attended university and his flamboyant record – as curate of Bovingdon, he had been involved in an "unseemly brawl" during a burial he was officiating.

Three former students have won the Victoria Cross: Arthur Mayo during the Indian Mutiny; and George Pearkes and Brett Mackay Cloutman, both during the First World War.