What is the name of the school headmaster at Chilton?

Charleston is the headmaster of Chilton on Gilmore Girls.

Headmaster Charleston oversees the elite preparatory school Rory attends after leaving Stars Hollow High. He is a formal authority figure who evaluates students, manages discipline, and represents Chilton's demanding academic culture.

Rory first encounters Charleston when her admission to Chilton becomes central to the show's opening story. Paris Geller is also a prominent Chilton student, and the headmaster's decisions affect both girls during their school years.

The character is played by Dakin Matthews. Viewers sometimes remember the institution but not the headmaster's name because Charleston appears less often than Rory's classmates and teachers. His surname is the canonical short answer.