Chilton is a co-educational prep school catering for students from kindergarten to senior level that Rory attends from Season 1 through Season 3. It is located in Hartford and is a prestigious school to attend, Rory gained attendance there in her sophomore year of high school. Chilton is highly competitive, and, as Hanlin Charleston once put it, while failure is a part of life, it is not a part of Chilton. Most students attending Chilton end up at an Ivy league school.
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| - Chilton is a co-educational prep school catering for students from kindergarten to senior level that Rory attends from Season 1 through Season 3. It is located in Hartford and is a prestigious school to attend, Rory gained attendance there in her sophomore year of high school. Chilton is highly competitive, and, as Hanlin Charleston once put it, while failure is a part of life, it is not a part of Chilton. Most students attending Chilton end up at an Ivy league school.
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| - Chilton is a co-educational prep school catering for students from kindergarten to senior level that Rory attends from Season 1 through Season 3. It is located in Hartford and is a prestigious school to attend, Rory gained attendance there in her sophomore year of high school. Chilton is highly competitive, and, as Hanlin Charleston once put it, while failure is a part of life, it is not a part of Chilton. Most students attending Chilton end up at an Ivy league school. The Chilton parents are expected to be highly involved in activities at Chilton, participating in things such as bake sales and fund-raising, through associations such as the Booster club. These clubs also have faculty representation. They have files on each parent which contain details of their participation in such events. When Lorelai went to complain to Headmaster Charleston, he presented her with her file which was incredibly thin and contained no evidence of her work. Notable characters to arise from Chilton include Paris's oldest friends Madeline Lynn and Louise Grant who both attended the school for a long time, and played active roles in The Franklin and Student Government, but were often too preoccupied with boys and clothes to study. Tristan Dugray was the main love interest at Chilton, but transferred to military school after he stole from his friend's dad's safe. It was a form of punishment demanded by his father. Max Medina, Rory's English Lit teacher, played a major role in her success at Chilton. When she was late for a very important quiz on Shakespeare and was not allowed to make it up, he organized some extra credit work for her with the Headmaster in order to keep her grades up. He was also affianced to Lorelai Gilmore after dating her for several months. They split up right before their wedding due to Lorelai breaking off the engagement.
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