The Pilgrims’ School

Head: Dr Sarah Essex
Telephone: 01962 854189
School Address: The Pilgrims' School 3 The Close Winchester SO23 9LT


Boarding Type: Full Boarding
School Type: Boys

Head of Boarding: Tom Rainer, Deputy Head Pastoral and Director of Boarding (from September 2021)
Head of Boarding Email:

The Curriculum

School is exciting, learning is exciting. Pilgrims’ is a place of outstanding personalised learning and teaching. We take great care to ensure that the interests and specific talents of each boy are valued and developed across our broad curriculum, co-curriculum, and extra-curriculum.

Games & the Arts

A progressive approach to games; traditional sports are played daily. Winter games are football, rugby and hockey. In the summer, cricket and athletics. Art, drama and design & technology are much loved. Music is an exceptional strength.

Pastoral Care

Our pastoral care is exemplary. Not only do we have a deputy head pastoral, a director of wellbeing and a lay chaplain, we also have heads of year, form teachers and vertical tutor groups looking after not just the academic but also the pastoral life of the boys. In addition, we have a team of boarding house parents, nurses and matrons working together to provide excellent care.

Recent Scholarships

Winchester College, Eton, Radley, Canford, Sherborne, Marlborough, Magdalen College School: academic, music, art, sport.

Head Teacher’s Philosophy

The Pilgrims’ School is the perfect place for boys from reception to year 8 to learn and grow up – to find their passions and nurture them. It is a place of outstanding personalised learning and teaching. All boys move onto their senior schools with confidence having made excellent progress academically and pastorally.


We have two boarding houses, Main School and Q School. Both enjoy the same friendly, bustling, family atmosphere.

The dorms have all been decorated with boys in mind. Each has its own, distinctive theme, including (to name just some) a superhero dorm, surf shack, Beano room, and sports den. They are well-furnished, light and airy, with plenty of space for home clothes, books, and teddy bears. The boys make their dorm a cosy home from home with their own duvet covers and posters and family photos on the walls. Each dorm has a radio alarm which is set to wake the boys gently each morning in time for breakfast. The shower rooms and bathrooms are conveniently arranged to adjoin the dorms, and full laundry facilities are provided in house.

Main School is upstairs in the main building at Pilgrims’. It is the boarding house for all the Choristers, the junior Quiristers and a large number of boys from all the year groups. Boarders have easy access to the school’s sports and recreational facilities in the evenings and at weekends – the Puddle, cricket nets, adventure playground, IT room, Priory games room, Briggs Library, the art studio, as well as a boarders’ cinema room and Numnums, the tuck shop.

Outstanding Characteristics

· Pilgrims’ is a day and boarding school for boys age 4-13

· A double choir school

· Outstanding academic results

· Feeds top independent schools in country

· Unique position, between Winchester Cathedral and Winchester College.

· Delicious food cooked on-site using fresh local ingredients.

· Exceptional pastoral care.