The Upper School Chorus and the Pennington Singers have a performance schedule both within the School community and in the broader region. These groups perform at the School's weekly chapel services, in the annual Candlelight Service in December, community meetings, and in concerts during the fall and spring. Vocalists from the Upper School Chorus and the Pennington Singers frequently have leading roles in the winter musical and also perform in other on-campus performances. In the Middle School, students can elect to sing in a vocal ensemble that performs for school concerts, student meetings, and events.

The Pennington Singers is a select choir whose members are chosen through an audition process. The Pennington Singers participate in a two-day retreat off campus in late fall. Students in Pennington Singers tend to be leaders in other music groups, and work towards taking our most challenging academic courses in music theory and composition. Members of the ensemble play a major role in choosing the music the group performs and determining the direction of the group.