Highfield

Highfield (13+ boys)

Highfield is one of the three ‘hill houses’ at the southern edge of town, a brisk six-minute walk from school. Boys enjoy the house’s convenient location next to the expanse of the Middle Playing Fields, and the School’s astroturf pitches and all-weather tennis courts.

Highfield was built in 1863 and has been extended over the years to accommodate the demand for more space.

Today, the House is well-equipped with communal areas, a games room, TV rooms, common room areas and cooking facilities for the boys.

Home to 50 boys, Highfield has small two-bed or four-bed dormitories for Fourth Form and Lower Fifth pupils, along with individual studies. Upper Fifth and Sixth Form boys have their own single bedsits.

Housemaster: Richard Hegarty
Richard has been at Uppingham since 2004, and has been the Housemaster of Highfield for the past ten years. The 2025-26 academic year will be Richard's final year in charge of Highfield.

Housemaster Elect: Gareth Hook from September 2026
Gareth Hook has been appointed as the next Housemaster of Highfield. Gareth, currently Head of Economics and Business at Uppingham, will bring to the role a strong track record of successful academic leadership together with extensive pastoral experience. Before joining Uppingham, Gareth was Head of Economics, Business and Enterprise and Assistant Housemaster at Lord Wandsworth College, and Assistant Housemaster and Senior Tutor at Millfield School. He has been integral to the development of pastoral programmes, mentoring systems, and initiatives that have developed house culture. Outside the classroom, Gareth is a keen sportsman and coach - playing cricket, golf, and squash, and coaching rugby - and he enjoys contributing to the wider co‑curricular life of the school.

Housemaster Elect: Gareth Hook
from September 2026

Gareth Hook has been appointed as the next Housemaster of Highfield. Gareth, currently Head of Economics and Business at Uppingham, will bring to the role a strong track record of successful academic leadership together with extensive pastoral experience.

Before joining Uppingham, Gareth was Head of Economics, Business and Enterprise and Assistant Housemaster at Lord Wandsworth College, and Assistant Housemaster and Senior Tutor at Millfield School. He has been integral to the development of pastoral programmes, mentoring systems, and initiatives that have developed house culture. Outside the classroom, Gareth is a keen sportsman and coach - playing cricket, golf, and squash, and coaching rugby - and he enjoys contributing to the wider co‑curricular life of the school.