Prior to the Christmas Break, each of the divisions at Stuart celebrates Christmas.

The Lower School celebration features songs and readings, along with special selections performed by the Stuart hand-bell choir. Parents and special friends are invited to attend the daytime celebration, after which the classes gather for individual parties. Santa also makes an appearance, and brings each child a gift.

Students in the Middle and Upper School hold their celebration the evening just prior to Christmas break. Called Evensong, the celebration is a liturgical service featuring The TartanTones, Stuart's vocal ensemble. Readings and prayers are interspersed with carols, anthems and instrumental offerings, and Cor Unum is candle-lit and festively decorated by the Stuart Parents Association. This is an elegant event in the life of Stuart.

Students in the Middle School gather for a party with their classmates. Upper School have also long celebrated a Christmas tradition known as "Kris Kringle." For many days leading up to Christmas break, students engage in secret gift-giving. On the final day before break, they gather in the gym to discover the identity of their benefactor.

The Tartantones sing "Night of Silence"