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.
The Student council is made up of a President, Vice President, Secretary, Treasurer, as well as student class presidents from the Senior, Junior and Sophomore levels. In their Senior year, Paris was the Student Body President and Rory was the Vice-President, leading to reformations in regards to the Library and Higher Hem Lines.
They were a secret society and they all sat on one table. They were one of the seven secret societies on the campus, all those worth mentioning. Paris' entire family were Puffs and was desperate to join them, if only for the connections she would later make in life. Rory guaranteed that could happen.
- The school was founded in 1803, celebrating its bicentennial in 2003.
- Its school colors are blue and white (silver), and the students attending Chilton are required to wear a uniform.
- For girls, the uniform consists of blue and white plaid skirt, blue blouse, navy blue tie and any combination of a sweater vest (blue or gray), sweater (blue) and blue blazer.
- Boys attending Chilton wear pale khaki pants, blue dress shirt and ties, and a blue blazer.
- Rory also hosts a student from Chilton in her sophomore year at Yale.
- The marble floors in the lobby were once walked on by Harriet Beecher Stowe.
- Robert Frost donated to the main staircase's banisters.
- Thomas Edison ceremonially lit a sconce on campus.
- It can be assumed that tuition at the school is less than $25,000 per year, as Lorelai's $75,000 check paid her parents back in full for the entire three years Rory spent there, and in later episodes Lorelai and Rory mentioned there was some money left over from the loan in order to help pay for her Yale tuition.
- Tuition is comparable to that of a state university.
- Class sizes are small because of the exclusivity of the school – Rory's senior class consisted of 45 students.
- Lorelai wanted to carve her and Rory's initials into a wooden column, but Rory talked her out of it.