LORELAI: We could go to sleep.
RORY: Mm, it’s 8.23.
The B&Bers have been carousing for three hours, so cocktail hour began at 5.20 pm, suggesting that Lorelai and Rory arrived at The Cheshire Cat between 4.30 pm and 5 pm, giving them ten to twelve hours on the road for something that should have taken them three hours. That’s a lot of aimless wandering.