Because they were only just 'over the wall', we caught up with these six scholars one term on, to ask how the transition felt, and what, exactly, Pilgrims' had given them in preparation.

For Javier, the move felt like a natural progression,  

'At Pilgrims’ there are lots of boys who share similar interests,' he says. 'It was nice to gather some friends before I started, and the teaching style is quite similar. It takes a couple of weeks to adjust – you just need to get organised, but I’ve been well-prepared.'

'The teachers understand what’s needed for Winchester College. It helps you get into a routine, so you can really hit the ground running.'

Alfie agrees. Sitting comfortably in his new routine, he credits Pilgrims’ with instilling something more than academic confidence. 

'The support from the teachers was incredible,' he says. 'The routine really got that working mentality going. I loved my time there, musically, academically and in sport. It’s a really nice place to get a good start in life.' 

For Matthieu, preparation revolved around exam technique;  

'Pilgrims’ helped a lot with exams,' he explains. 'They give you the knowledge for everything, and they tell you the format of Winchester, but that can be transferred to any exam. More than that, they teach you to take care of yourself. There’s a lot of positive reinforcement, so you can make as much progress as possible at senior school.' 

The emphasis on self-management is already feeling like a common theme. Zachary, who joined Pilgrims’ in Year 5 and is now  a scholar at Winchester, talks about the traditions he’s now encountering there: 'old, perhaps, but actually quite interesting' and how familiar routines smoothed the transition. 'At Pilgrims’ you’re used to getting up early for music practice,' he says. 'We even used the Winchester College Sports Centre for squash and basketball. Compared to other prep schools, having access to those facilities is an extremely good way to enhance your sporting ability.' 

Nathan, another scholar, joined Pilgrims’ later, in Year 7, but he also appreciated the nudges he got at Pilgrims’ towards independence. 
'Self-regulation is really important,' he says. 'Pilgrims’ does well in preparing you for that towards the end. They walk you into it, while still giving you support.' 

Learning to live together

Does that preparation extend beyond the classroom – especially to boarding? Thomas thinks so. 

'In boarding, you learn you have to get along with your peers,' he says simply. 'If you’re nice to them, they’ll be nice to you. I’d recommend boarding to most people. It’s a great learning experience; it makes you more tolerant and more open-minded.'

Zachary echoes the point. 'You have to learn to get along with other people,' he says. 'It’s a very good way to prepare you.' 
 

Magic moments

We asked the boys if they could pick one Pilgrims’ magic moment. Alfie remembers the Chamber Choir tour to Sorrento. 
'That was really memorable,' he says. 'I met so many lovely people, and it strengthened the bonds within the choir. It’s hard to choose just one.' 

For Matthieu it was the residentials, 'The leavers’ trips were incredible,' he says. 

For Thomas, the magic came on the sports field.
'We had a cup match against Kingston Grammar School in Year 8 and won in extra time,' he recalls. 'The feeling on the bus ride back was amazing. On the field you’re too focused to take it in, but afterwards you can reflect. Reflection is really important.' 

Zachary’s highlight was football, pure and simple. 
'I loved playing with my friends,' he says. 'I was first XI captain, and both on and off the pitch it was a really good experience.'

From Pilgrims’ to Sherborne

At the Choristers’ Carol Service on 18 December, another recent leaver, Sam, returned. A chorister from 2019 to 2025, he’s now at Sherborne. Walking through the Pilgrims’ Hall, he remembers performing on the stage in front of the whole school. 'That really boosted my confidence,' he says.

Music remains central to his new school life. 'I’m doing lots of music at Sherborne, and I’m also studying music online now. That’s a whole new realm, and it’s very exciting.' 

The move to senior school, he says, was remarkably smooth. 
'Boarding from a young age really helped. Academically, Pilgrims’ set me up very well. I find it quite easy now, to be honest.' 

He still smiles at the memory of discovering he’d won a music scholarship. 
'All the teachers told me to go to the headmaster’s office and I thought I was in serious trouble,' he laughs. 'So it took me completely by surprise.' 

Like so many alumni, Sam’s earliest memory is of his first Pilgrims’ carol service. 'All the lights were off, just candles. I’d never done church singing before, especially in the cathedral; it’s huge! It was daunting at first, but over time it became quite homely.'

From Pilgrims' to Eton

Nathan's family lives in Winchester, so he paid us a visit at the start of the Christmas holidays following his first term at Eton, where he went as one of the annual cohort of 14 King's Scholars.

'Pilgrims' was very personalised, you had your own tutor, and Eton has that too, and since I'd boarded from year 4 it was quite easy to fit in. Pilgrims' was like my second home.'

At Eton, Nathan is continuing the musical education he started at prep school.'I play the viola, the violin and the piano, having started the viola in year 7 at Pilgrims'. My first concert at Eton was a Brandenburg concerto written specifically for the viola'. He also plays rugby, having started touch rugby at Pilgrims' and has taken up fencing. 

Nathan says the memory from Pilgrims' he'll treasure is, quite simply, 'being in the dorm with my friends'.

We would love to catch up with all 2025 Leavers to hear how your first term has been and the transition to senior school. Please do get in touch whenever is convenient, or you can just email a line or two and a photograph you are happy for us to share, so that we can capture this special moment in time.

Jane Goddard
Marketing and Communications