There are choirs for boys in each of the Junior, Middle and Senior School, and they perform in both Concerts and Chapel services.

The Chapel Choir is the most advanced performing group in the school. It sings in Choral services during the term, as well as presenting at the annual Carol Service held in the beautiful setting of Eton College Chapel, an Easter service and at various other occasions throughout the school year. It also performs on several occasions outside Caldicott each year. This might be singing a service as a guest choir, such as in a Public School or a local Church (e.g. Hedgerley, Stoke Poges), and singing at weddings or for local events such as the Child Bereavement Charity annual Carol Concert in Marlow, to give just a few examples.

At least 60% of the boys in the school learn musical instruments, taught by a team of visiting instrumental teachers. All the main western orchestral instruments are taught, as well as piano, saxophone, guitar, singing and even bagpipes. There are several chamber groups of varying size and style, from String Quartet to Jazz quartet, and a variety of larger groups such as String Orchestra, Wind Band and Big Band. They perform frequently during the course of the year. There are several instrumental concerts in the year for Junior, Middle and Senior School performers, a mid-year concert for groups, a Junior School presentation of Music, Art and Technology a Middle School presentation of Music and Drama, a Leaver’s Concert, and several small-scale concerts called Platforms for boys who have not played in public before.

All boys taking lessons contribute to the House Music Competition and compete through two rounds for a place in the Final. This final is a public concert, and is adjudicated by a professional musician, usually a Director of Music from a prominent Public School. Boys take Associated Board Music Examinations (ABRSM) as and when they and their teacher deem them to be ready, and only with the agreement of the boy, parents and teacher. These exams are not mandatory at Caldicott.

There are other musical events such as Beatlemania, Showstoppers, more recently Star Factor (March 2007) and Tango Volcano (October 2007), which offer opportunities for boys to take part and parents to enjoy a social evening with music and perhaps snacks or a buffet supper. The music department often arranges for visiting artists to perform in the recently built Centenary Hall. The Caldicott Concerts scheme exists to provide the whole school with the experience of attending a professional performance at least once every year. The visiting artists give a presentation and workshop to the whole school in the afternoon, and then put on a public concert in the evening from which the ticket sales will pay for the artists visit. Examples of this are The Band of the Blues and Royals, Demon Barbers, Ensemble Bash, NewNoise, Joby Burgess and the pianist, Richard Meyrick. Some of our previous concerts can be viewed in Past Events, including the 2004 Centenary Arts Festival.