The school is a major centre in Wales for the Gold Award of the Duke of Edinburgh Award Scheme and younger pupils also participate in the Scheme at Silver level. In so doing they enjoy new experiences and develop skills of leadership and self reliance. Expeditions have taken place in the Forest of Dean, Black Mountains and Brecon Beacons. In the service section of the award scheme, boys are working in local charity shops, helping the local old age pensioners with their gardens and shopping, and local primary schools have been given assistance by older Monmouth School for Boys students.
The skills being undertaken are diverse in their nature, with sheep breeding and karting through to clay-pigeon shooting and scuba diving. The physical recreation section of the award has enabled boys to try their hand at basketball, caving, orienteering and even hang-gliding!
As part of the Gold Award scheme, boys have to undertake a residential course for five days. Students have attended military courses and many boys, particularly potential medics, have joined the Winged Fellowship Trust to help people less privileged than themselves.