The flagship of the Somerset College Outdoor Education Programme is the Trek, a 27-day journey of self-discovery undertaken by all Grade 9 students in November each year, during which time they cover 360km on foot, in canoes and on bicycles. It is a remarkable journey that starts on foot from the school and ends on the beach in the De Hoop Nature Reserve.

The entire Grade 9 year group is divided into single-sex groups of approximately fourteen students and each group is allocated two adults; some of whom are teachers and some past-students. Students are given the opportunity to lead their group each day, make decisions affecting the group, prepare meals, write letters to family and friends and learn camping skills, orienteering and general survival. The students are not permitted to bring cell phones or any electronic devices. It is a special time of reflection, adventure and mental, spiritual and physical growth – a true rite of passage.