Early in the episode it becomes apparent that the town of Stars Hollow is about to celebrate its annual Autumn Festival. This is the first major celebration we see in the town, and like the other town festivals, it demonstrates the change of seasons and the turn of the year, just as the Friday Night Dinners wrap up each week for the Gilmores.
The flow of time is one of the primary themes of Gilmore Girls – take notice of how often clocks, watches, calendars, running late, and being short of time are mentioned. Already Rory has had a late acceptance to Chilton, Lorelai has woken up late for Rory’s first day at school, Rory has missed an important test because she arrived too late, Lorelai has fumbled her first date with Max because of time management problems, and missed a relative’s funeral because of the day of the week, and Jackson has felt a shift in the spacetime continuum (suggesting that time in the show is cosmic in its scale).
It is not possible to tell from this episode when the Autumn Festival is held: just that it is in November before Thanksgiving. However in A Year in the Life, it is confirmed that the Autumn Festival is the first weekend in November. We can feel fairly confident that the main events of the episode occur around that time.
(The pumpkins used to decorate the set for the Autumn Festival scenes ended up rotting and emitting a putrid smell. After that, fake pumpkins were used for any autumnal celebrations in Gilmore Girls).