Season1, Episode 2.  It’s Rory’s first day at Chilton, and she and her mother sit in their car outside of the school looking at building and noting how menacing it looks with all the gargoyles and its gothic structure. 

A Year In The Life - Summer. 

Season 2, Episode 10.  Paris Geller states that rereading the Iliad three times is not doing anything for her. 
Season 5, Episode 22. Lorelai reveals that Rory once grounded herself for forgetting to return a copy to the library.

 Season 3, Episode 16. Lorelai reads this at the beginning of the episode.

Season 7, Episode 1. Post-Luke break up, Lorelai collects all the objects that remind her of him, including this book. 

Season 3, Episode 13.  We see Jess reading this when Dean walks into the diner. 

Season 2, Episode 15.  The Buy a Book! Fundraiser is in town.  A bargain at only 75 cents! 

Season 7, Episode 8.  Logan says “You clearly think you are. Why? Because you read Ironweed? ‘Cause you saw Norma Rae?” 

  A Year In The Life - Spring. 

Season 2, Episode 10.  Lorelai jokes that her parents are the Joyless Luck Club as they’ve been squabbling for weeks.