As Rory's (Alexis Bledel) graduation day approaches, the Gilmore girls plan their long-awaited summer backpacking trip across Europe, even as Lorelai (Lauren Graham) faces the possibility that the recent fire will force the owners of the Independence Inn to sell the building. Rory takes matters into her own hands when she discovers that Lorelai is making a great personal sacrifice to pay for the Yale tuition. Richard (Edward Herrmann) and Emily (Kelly Bishop) present Rory with a lavish graduation gift, and everyone is touched by Rory's moving valedictory speech. Meanwhile, Luke (Scott Patterson) has second thoughts about a summer cruise with his new girlfriend.
- Lauren Graham as Lorelai Gilmore
- Alexis Bledel as Rory Gilmore
- Keiko Agena as Lane Kim
- Melissa McCarthy as Sookie St. James
- Yanic Truesdale as Michel Gerard
- Scott Patterson as Luke Danes
- Liza Weil as Paris Geller
- Jared Padalecki as Dean Forester
- Milo Ventimiglia as Jess Mariano
- Sean Gunn as Kirk Gleason
- and Kelly Bishop as Emily Gilmore
- special appearance by
- Edward Herrmann as Richard Gilmore
- Liz Torres as Miss Patty
- Michael Winters as Taylor Doose
- Sally Struthers as Babette Dell
- Jackson Douglas as Jackson Belleville
- Dakin Matthews as Hanlin Charleston
- Shelly Cole as Madeline Lynn
- Teal Redmann as Louise Grant
- Adam Wylie as Brad Langford
- Grant Lee Phillips as Town Troubadour
- Ted Rooney as Morey Dell
- Rose Abdoo as Gypsy
- Headmaster Charleston, faculty members, fellow students, family and friends, welcome.
- We never thought this day would come.
- We prayed for its quick delivery, crossed days off our calendars, counted hours, minutes and seconds and now that it's here, I'm sorry it is, because it means leaving friends who inspire me and teachers who've been my mentors, so many people who've shaped my life, and my fellow students lives impermeably and forever.
- I live in two worlds. One is a world of books.
- I've been a resident of Faulkner's Yoknapatawpha County, hunted the white whale aboard the Pequod, fought alongside Napoleon, sailed a raft with Huck and Jim, committed absurdities with Ignatius J. Reilly, rode a sad train with Anna Karenina and strolled down Swann's Way.
- It's a rewarding world, but my second one is by far superior.
- My second one is populated with characters slightly less eccentric, but supremely real, made of flesh and bone, full of love, who are my ultimate inspiration for everything.
- Richard and Emily Gilmore are kind, decent, unfailingly generous people. They are my twin pillars, without whom I could not stand. I am proud to be their grandchild.
- But my ultimate inspiration comes from my best friend, the dazzling woman from whom I received my name and my life's blood, Lorelai Gilmore.
- My mother never gave me any idea that I couldn't do whatever I wanted to do or be whomever I wanted to be.
- She filled our house with love and fun and books and music unflagging in her efforts to give me role models from Jane Austen to Eudora Welty to Patti Smith.
- As she guided me through these incredible eighteen years, I don't know if she ever realized that the person I most wanted to be was her.
- Thank you Mom, you are my guidepost for everything.
- ❝I think I may have loved you. But, I just need to... let it go❞
- —Rory to Jess
- In the episode Swan Song, Emily mentions that Gran will be at graduation when trying to scare Rory into meeting Jess, pointing out that Emily, Richard and Gran will get to meet him at the same time at graduation. However, Gran is not present, nor is there any mention of her absence.
- Brad sings "Cherish" by The Association
- "Peace Train" by Cat Stevens
- "Mexican Shuffle" by Herb Alpert and the Tijuana Brass
- Moby-Dick by Herman Melville
- Adventures of Huckleberry Finn by Mark Twain
- A Confederacy of Dunces by John Kennedy Toole
- Anna Karenina by Leo Tolstoy
- In Search of Lost Time by Marcel Proust
- William Faulkner
- Jane Austen
- Eudora Welty
- Lorelai – The Love Boat
- Luke – I have no plans to propose.
- Lorelai – You don't now but after you've had dinner at Captain Stubing's table, and Isaac's served you up a couple of mojitos...
- Kirk – I did tell you about the dangers of mold and Ed McMahon's dog, right?
- Sookie – Tell it to Deney Terrio here. "I should've been a dancer."
- Lorelai – Look, if you need to work as a low-paid intern for a magazine or a stringer for some small-town newspaper or Tom Brokaw's toupee comber-outer before you make real money, then that's what you'll do.
- Lorelai – If you wear it with a moody look on your face like you're thinking of Bolsheviks, they'll mistake you for Simone de Beauvoir
- Lorelai – We're the Chilton equivalent of 50 Cent's posse.
- Rory – I don't want you to defer your dream
- Sookie – I've been depressed for days. I couldn't watch The Dating Game anymore.
- Brad – Though my time here was briefly interrupted by my period spent on Broadway hanging out with Stephen Sondheim
- Rory – This marble is two hundred years old. Harriet Beecher Stowe walked on this marble.
- Lorelai – Oh, the banister.
- Rory – Was donated by Robert Frost
- Lorelai – The sconce.
- Rory – Was ceremoniously lit for the first time by Thomas Edison
- In the scene where Lorelai is telling Rory about the money issue her shirt only shows "PEAC" because her sweater is covering the "E" but in the next shot "PEACE" is showing.