[Rory and Jess are walking toward her bus]
RORY: I think this one’s mine.
JESS: Yup, the sign says Boonesville.
The “boondocks” or the “boonies” is American slang for a distant or remote rural location, especially one with few amenities. “Boonesville” is obviously a town in the boondocks.
The word boondocks comes from the Tagalog word bundok, meaning “mountain”. It was coined by U.S. Marines fighting against Filipino guerrillas after the Spanish-American War (1899–1902), for the rough hill country there. Later, American troops in the Philippines during World War II shortened it, and after the war it began to be used more widely.
Although we can’t be certain what time it is when Rory goes to the bus terminal with Jess, the express bus she took in the morning takes two and a half hours to get to New York, so to arrive in Hartford by 5.30 pm in order to be at the graduation ceremony by 6 pm, she cannot plan to leave any later than 3 pm.
Assuming Rory met Jess in Washington Square Park some time after midday, they have had time to eat lunch and catch the subway to a record store before coming to the bus terminal (which should have only taken 15 minutes to Times Square on the subway). They could have easily spent two, or two and a half hours together in New York.
Rory probably thinks she has timed everything perfectly – oh, how wrong she is!