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The Pilgrims’ School, Winchester

This musical day and boarding prep choir school in central Winchester is proudly traditional with a 21st-Century outlook


Pilgrims' School Winchester

Tucked away beside the Cathedral and Winchester College in the heart of Winchester, The Pilgrims’ School is a boys’ day and boarding prep Cathedral school. Named after its medieval Pilgrims’ Hall when the school was founded in 1931, Pilgrims’ has some serious history behind it: the school’s lineage has been linked to Winchester Cathedral since Saxon times.

Today, 247 pupils aged 4 – 13 are taught in manageable classes of a maximum of 16 with a ‘no ceiling’ attitude to learning that sees young leavers move on to top independent senior schools. The school, unsurprisingly, has a Christian ethos, but welcomes children whatever their beliefs.


The Puddle swimming pool at Pilgrims' School Winchester

Beautiful wood cladded walls and tiled stone floors greet visitors walking into the main building, which was redesigned in the 17th century and sits on the site of former Roman and medieval buildings. To the rear, the site opens into a large quad, with a 20-metre heated open air swimming pool (‘The Puddle’) in the centre, used to teach boys from Year 1 upwards through the summer and into autumn (in winter, Pilgrims’ boys use the Winchester College pool).

The Pilgrims’ Hall dates back to the first half of the 14th century – a big draw for visiting history buffs. Still used extensively for music and drama, the most recent production staged here, The Lion King, involved a cast of 90 pupils aged 7 – 10. A West End-spec sound system brought 21st century production values to the show, with the lighting impressively operated by a technically minded Year 8 boy. In the Senior school-standard DT room, I spot decent kit like a laser cutter and 3D printer, along with a few very impressive speakers all designed and made by the pupils, who are allowed to listen to music while they work.

The River Itchen running through Pilgrims' School Winchester

Housed in its own purpose-built centre, the Pre-Prep building has good-sized play equipment and a separate, all-natural materials play area for the youngest and a mini-bug hotel currently under construction. It sits next to the gorgeous Deanery Garden and a tributary of the River Itchen. Leading out to extensive games pitches with views of the Bishop’s Palace and the ruins of Wolvesey Castle, it’s hands-down one of the most tranquil spots in the city.

The youngest boys also get their fresh air by heading off to Forest School through a ‘secret’, ivy-clad wooden door that leads out to the Bishops Palace Arboretum and the school’s extensive Wolvesey playing fields. Set within the old city walls, they’re bordered by a ruined castle and the Bishop’s Palace. Along with the open-air swimming pool, there are cricket nets on site, plus plenty of facilities a short walk away at Winchester College, including fives courts, sports hall, rowing facilities, tennis courts and astro turf, plus and a new sports hall and swimming pool, due to be completed in 2023.


Football being played at Pilgrims' School Winchester

Sport is important at Pilgrims’, which holds its own against local rivals. Teams are competitive in football, rugby and cricket, as well as swimming, water polo, athletics and Winchester Fives. In the last five years, Pilgrims’ boys have earned sport scholarships to Millfield, Bradfield, King Edward VI Southampton, Winchester College and Radley.

Big tournaments include ISFA (Independent Schools Football Association) cups at U13 and U11, the Rosslyn Park rugby sevens and national athletics and swimming competitions and the Independent Association of Prep School’s annual clay pigeon shooting tournament. The PE, Games and co-curricular programme also includes badminton, basketball, cross-country, fencing, gymnastics, hockey, orienteering, rowing, tennis, judo, karate, rowing, squash, sailing, tennis, golf, fencing and fishing. Phew!


Boys playing instruments music  Pilgrims' School Winchester

A huge calling card for the school, the Music Department is strong – instrumentally as well as vocally. Alongside lessons for all taught by the Director or Assistant Director of Music from reception upwards, 29 visiting music teachers are brought in to teach the impressive 87% of pupils learning instruments (47% learn two).

The average mark in ABRSM assessments (the exam board of the Royal Schools of Music) is 124.3, the equivalent of a merit. Not surprisingly, it’s very rare here not to hear music piping out through open windows into the quadrangle, something the whole school community really embraces.

Choir Boys Pilgrims School Winchester

Previously part of neighbouring Winchester College, an independent boarding school for boys aged 13 – 18, the Quiristers of Winchester College Chapel Choir became part of The Pilgrims’ School in 1966, making it a double choir school. Choristers and Quiristers continue to be taught here as full or weekly boarders. Twenty-two Choristers sing with Winchester Cathedral Choir and 16 Quiristers sing with Winchester College Chapel Choir.

In 2021, nine Pilgrims’ leavers won music scholarships to Winchester, Sherborne, Harrow and Eton. Despite its size, Pilgrims’ fields a full orchestra (currently 58 boys) and has plenty of weekly ensembles too, including Sinfonia, Sinfonietta, Symphonic Wind Ensemble and Big Band. It’s not all pomp and classics here either – School of Rock and Battle of the Bands are really popular with the young cohort too.


Boarding dorm Pilgrims' School Winchester

Pilgrims’ has 100 boarding places, with the youngest in Year 4 (age 9). There’s full and weekly boarding with the option to go home for the weekend on Saturdays. Dorms have six or eight bunk beds and bright, themed murals on the walls, from Dr Seuss, Superheroes, Tintin, Beano and sports.

For those staying at the weekend, there are trips out to the beach, mountain biking in the New Forest, watching rugby at Twickenham, surfing or down to the river. I’m also whisked past the twice-weekly, boarders-only ‘Num Nums’ tuck shop by one of the cohort who confirms (with a grin) that the treat selection is pretty good.


Boys in classroom Pilgrims' School Winchester

Very strong. The combination of specialist subject teachers and ‘no limit’ belief in children’s ability takes Pilgrims’ pupils confidently on to their pick of senior school. Pilgrims’ is academically selective, with formal assessments for joiners from Year 3. In 2021, a third of leavers, who mostly stay on until 13, won scholarships. Most (39%) were to Winchester College but other scholars went on to the likes of Eton, Sherborne, Charterhouse, Radley, King Edward VI, Canford, Marlborough, PGS, St Edward’s Oxford and Harrow.


Heads of Year, form teachers and vertical tutor groups work with the Deputy Head Pastoral, Director of Wellbeing and a Lay Chaplain to provide pastoral care, with boarding house-parents, nurses, and matrons additionally looking after the wellbeing of boarders. The Director of Wellbeing is a Youth Mental Health First Aid trainer and teaches mental health awareness to boys as part of PHSEe.

Recognising that different children respond to different adults, all Pilgrims’ staff are training in Youth Mental Health First Aid. Dedicated pastoral support is provided in groups and individually and there’s termly small group talking sessions for Year 7 with the Head Nurse and emotional literacy programmes for boys in Year 2 and 3 with the Director of Wellbeing.


Dr. Sarah Essex Headteacher Pilgrims' School Winchester

Sarah Essex joined The Pilgrims’ School in 2020, becoming its first ever female Head. Her impressive academic background includes first-class Honours degree in Natural Sciences and a PhD in Theoretical Inorganic Chemistry from Trinity Hall, Cambridge.

With an outwardly gentle demeanor and a vocational drive that saw her give up a successful strategy consulting career, she changed path after reading a report of lack of qualified science and maths teachers in UK primaries. Initially voluntary teaching one day a week at her local parish school and other primaries in London and from Essex to Hereford and Worcestershire, after giving up consulting and studying for her PGCE, she took a job teaching Mathematics at The Hall, a boys’ prep in Hampstead. She worked her way up to Head of Department and senior leadership, then moved to Fulham School, where she was Deputy Head Academic of Fulham Prep before being appointed Head of Pilgrims’.

A big advocate of single-sex education, the fact that Essex has embraced the academics, music and values-driven ethos of manners and a brotherly kindness to younger pupils’ has been welcomed by parents. Yet, while she is determined to protect the many traditions that give the school its distinctive character, she tells me she isn’t afraid to evolve, as evidenced by staff restructuring and new additions to the senior leadership team. This includes a new Head of Digital Learning, brought in to ramp up digital skills in lessons throughout the curriculum and put more emphasis on computer science and coding.


Where to begin? The colour-coded Choristers, perhaps. Known as the Cs and Qs or ‘the reds and the blues’ 22 cathedral Choristers sing with the Winchester Cathedral choir while 16 college Quiristers sing with the Winchester College Chapel Choir (Choristers wear red jerseys, Quiristers wear blue). Along with French, taught from reception, Latin and ancient Greek are taught from year 6.

Outdoor chessboard Pilgrims' School Winchester

One of many after-school activities, known as ‘commoners’, chess is big at Pilgrims’ – but more unusually (and fun), it’s often played on a giant outdoor chess board. Alongside the usual sport and drama, the 40 – 50 commoners clubs include fly fishing, Russian, knitting, water polo, Dungeons and Dragons and The Copernicus Society (first rule – never talk about The Copernicus Society…).

Special mention, too, for the fantastic Tardis right in the middle of the main library, built by a clearly very talented Design Technology teacher.


For day pupils, breakfast club starts bright and early at 7.15. After Prep, boys can take part in clubs (commoners) from 5-6pm. After school care is also available for younger boys until 6pm and covers homework, reading as well as activities like Lego and construction followed by a hot, cooked meal before pickup.


The last ISI Report was a Regulatory Compliance Report in 2019.


Day boys can’t bring mobile phones to school but boarders can use them for 40 minutes in the evening before devices are locked away. Boarders have device-free nights on Mondays and Thursdays, with the option to use the school’s iPads or landlines to call home.


Day boys arrive at two locations at opposite ends of the school met by the head and senior leadership team. Timings are staggered for the Pre-Prep who do a shorter day with the option to pick up before or after ‘commoners’ after-school activities. There’s also a morning shuttle minibus from the Winchester Science Centre, which has straightforward access from major routes, without entering the city centre.


Reasonable for the Pre-Prep, above average for the area for Year 3 and above, though past parents say it’s well worth it. Reception – Year 2 is £3914 per term; Year 3 is £6050. Day pupils in Years 4 – 8 are £6819; boarders are £8688. For Choristers and Quiristers (all boarders), the fee is reduced to £5213.


Pilgrims' School Winchester choir boys ice skating

Academics at The Pilgrims’ School are very advanced and previously, it has had a reputation outside of the school for being a bit of a hot house. However, current parents describe it as a happy and positive place. Pupils tell me they like the fact it’s single gender and are very positive about the teachers and cocurricular activities. While enthusiastic about the “incredible” experiences, one Chorister tells me his additional timetable demands can be hard going at times.


Good for: Bright, curious boys will thrive. The brotherly culture and impeccable manners gently instilled in the pupils will be especially reassuring for parents of boarders. There’s no guarantee of a place at the neighbouring Winchester College but many Pilgrims’ leavers do make the grade – or go on to other top UK independents.

Not for: Pilgrims’ is a top choice for plenty of different types of boys and families but the deep-rooted traditions here may not appeal to all. The city centre location might prove tricky traffic-wise for parents of day pupils.

Dare to Disagree?! Be my guest! To find out more about 2022/23 entry or arrange a tour, email The next open event is on Fri 25 March 2022.

The Pilgrims’ School, The Close, Winchester, 2O23 9LT. Tel. 01962 854189.

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