Skip to content ↓

School life


Boys are given the opportunity to take on roles of specific responsibility as they progress through the school. All of these relationships are fostered through a variety of activities over the year, and ensure all boys are fully a part of the Pilgrims’ family.

Shadows and substances

Each new boy is assigned a current Pilgrim in his form as a ‘substance’, a boy who will take especial care of his ‘shadow’ as he settles into the new routines at school. The substance will usually have contacted his shadow before he arrives at the school and will be a familiar face waiting for him on the first day of term.


Every boy in Year 3 is a ‘cousin’ to a boy in Year 2, which helps continue the link between the Pre-Prep and the Prep. 


In Year 5 boys have the opportunity to become monitors, taking responsibility for various areas around the school during a specific period and looking out for younger pupils. 


In Year 7, a boy may become a Listener.  A Listener looks out for boys who need help and is a helpful ‘brother’ figure.

Year 8

All boys in their final year have a role of responsibility within the school, enabling them to take opportunities to show initiative, to inspire younger boys, to learn the value of contributing to the community.


They all become an Uncle! Their nephews are the new boys in Year 3 for whom they have a special duty of care as they settle into the new routines of the school. The bond exists as another way of promoting positive relationships across the age groups.


Some become Prefects – the highest ‘office’ of responsibility for a boy in the school. Prefects meet regularly with the Headmaster to discuss the wellbeing of the school; they also advise him on a range of matters and have a chance to influence the strategic direction of the school. Others hold equally but differently significant roles. They may be a Set Captain; they may chair the school council – they may even be the boy who opens up NumNums, the tuck shop!

Our school council gives boys a voice in the school.  As well as being a vehicle for change and a forum for good ideas, it teaches responsibility and is ‘democracy in action’. Council representatives are elected from all year groups by boys in their tutor group. The boys set the agenda for council meetings, which are chaired by a Year 8, and proposals are put to the vote. Key life skills are developed as boys learn the importance of negotiation and diplomacy while presenting their case on behalf of their peers.  They also see their proposals implemented by the school, giving them an encouraging further step towards becoming agents of change in the world. 

Our Location

We are blessed with a truly idyllic location. Just an hour south of London by direct train, with easy access to all the major travel hubs, and yet we are surrounded by the stunning countryside of the South Downs National Park. The school is tucked away between Winchester Cathedral and Winchester College, within the secure and secluded Cathedral Close. Moments from our front door is the heart of the historic city of Winchester, or step through our back gate to find water meadows, countryside, and the South Downs Way.