The Princess Anne High School choral department presents an annual Holiday Concert for two nights in December. The 2007 show was held on December 6 and 7 at 7:00 p.m. in the auditorium.

Some years, with the exception of a few songs, each show is entirely different. Music ranges from the upbeat performances in Cool Yule and Santa Ma Jazz performed by the Madrigal Jazz Choir to traditional carols performed by the High Chamber Choir. One Magic Christmas performed by the Concert & Mixed Chorus classes is another show stopper.

At the conclusion of each show the chorus alumni are invited onto the stage to join the entire chorus in singing Vivaldi's Gloria and Silent Night.