Who is the headmaster of Chilton in Gilmore Girls?
Answer
Hanlin Charleston
Hanlin Charleston is the headmaster of Chilton in Gilmore Girls.
Charleston oversees Chilton, the elite preparatory school Rory attends after leaving Stars Hollow High. He is portrayed as formal, demanding, and closely connected to the world of wealthy New England families.
His decisions affect Rory and Paris Geller throughout their high-school years. He also knows Richard and Emily Gilmore socially, which gives the school’s administration a personal connection to Rory’s grandparents.
Max Medina is a Chilton English teacher and one of Lorelai’s romantic partners, but he is not the headmaster. That distinction is an easy one to miss because both characters are closely associated with Rory’s school.