Some draw to a close with a seismic jolt, a single moment that marks a sharp before and after. Others drift almost imperceptibly, their passing only noticed in hindsight, like tide marks left unremarked on a harbour wall. And sometimes, as is so often the case in real life, change comes in a middle register: with a recognisable turning point, yes, but with what follows being gentle, steady, evolutionary. 

This week has brought a small but poignant moment for Pilgrims’. As the front of house has been busy with the colour and liveliness of the end of term - school trips launching in all directions (seven in the last fortnight alone, including two residentials!) - something more subdued but still significant has happened behind the scenes: I have written the final Headmaster’s report to the Full Governing Body, ahead of their last formal meeting next week. In September, the Pilgrims’ Committee will come into being, beginning a new chapter, reporting up to the Governing Body of Winchester College. 

As I have emphasised of late - (but if something’s worth saying once, it’s worth saying twice) - while this is indeed a shift, it is not a rupture. It is the next step in a relationship of mutual respect and shared values, and one that has long been part of our story. It formalises a connection that has for decades been a part of our way of life, our outlook, and our boys’ education. 

Moments like this invite reflection. And in that spirit, I find myself thinking about one of the defining strengths of Pilgrims’: its deep sense of community. It’s not a vague concept here. It is lived, felt, and recognised: by governors, many of whom joined the Board after becoming part of the school family as parents or friends; by staff, whose devotion to the school goes far beyond the job description; and by our boys, who experience the joys and responsibilities of belonging to something larger than themselves. 

I’m especially mindful of this community spirit at a time when I’ve been interviewing candidates for roles over the last two weeks, including Assistant Houseparents in our boarding team. Again and again, the word ‘community’ has emerged as central - not just as a talking point, but as a genuine value. A strong boarding environment cultivates bonds that go deeper: between the boys, the staff, and often the families too. Where the hours are longest, there the community is strongest. Our Chorister and Quirister communities perhaps feel this most intensely, but it is something that resonates across the whole school. 

And it is not merely those currently within the walls who keep that spirit alive. The enduring glow of this community is fuelled by those who return, who remember, and who feel drawn back - evidence, if it were needed, of a culture that nourishes as well as educates. 

As we look forward to the season of sponsored walks, fêtes, School of Rock performances, community cricket matches, barbecues and more, there is no better moment to pause and give thanks for this community spirit. These occasions are not only sheer good fun; they reaffirm who we are. And I am pleased, truly pleased, that Winchester College, becoming our formal partner, understands and values this deeply. It is a precious thing. Many other prep schools have not been so fortunate in their transitions. 

I look forward to celebrating such occasions with you all over the coming weeks. With our Athletics Finals Day on Saturday 5th July, and in the spirit of shared joy and summer tradition, I warmly encourage you to bring picnic baskets and blankets, wear your brightest summer smart casual, and even wave a little bunting if you’re so inclined. 

Here’s to the final chukka! 

Tim Butcher
Headmaster