A still from Gilmore Girls season 1, episode 7 "Kiss and Tell," as Rory and Lorelai walk through Stars Hollow during the fall
(The WB)

10 best fall episodes of ‘Gilmore Girls,’ ranked

Around this time of year, it’s all about apple picking, pumpkin carving, spooky decor, watching the leaves change color, football, etc. You’ll find pumpkin soup recipes filling your FYP, and suddenly, you’re watching Rory Gilmore make another terrible decision. That’s right, you’re watching all of Gilmore Girls from the beginning on Netflix. 

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However, if you’re busy like me, you don’t have time to watch seven 22-episode seasons before switching to Halloweentown and Scream the last week of October. Here are The Mary Sue’s 10 best fall episodes of Gilmore Girls. 

10. Season 2, episode 4: “The Roadtrip To Harvard”

Lorelai checking out at an inn in Gilmore Girls "Roadtrip to Harvard"
(The WB)

Before Yale, there was Harvard, the school that Lorelai (Lauren Graham) and Rory (Alexis Bledel) had dreamed of since Rory was little. On this spectacular trip, the academia vibes are vibing, and these ladies are sitting in on classes and walking the campus. As much as this is a chance for Rory to see where she might spend four years once she graduates from Chilton, it’s also a time for Lorelai to reflect on who she could have been had she gone down a different path. 

9. Season 1, episode 7: “Kiss and Tell”

A still from Gilmore Girls season 1, episode 7 "Kiss and Tell," as Rory and Lorelai walk through Stars Hollow during the fall
(The WB)

An early and a goodie. This episode is filled with all the fall vibes of Gilmore Girls season 1 and the sweet innocence of Rory’s first kiss—if only we could block out the horrible things she and Dean (Jared Padalecki) will do down the road in season 4. “Kiss and Tell” solidifies the bond between Lorelai and Rory by showing just how much Lorelai cherishes her relationship with Rory and how deeply she’s affected by her daughter growing up. 

8. Season 5, episode 7: “You Jump, I Jump Jack”

Logan and Rory holding umbrellas in Gilmore Girls "You Jump, I Jump, Jack"
(The WB)

Sorority this. Fraternity that. Nothing screams Academia like secret societies that throw parties in the woods during the fall semester. Logan (Matt Czuchry) invites Rory to a Life and Death Brigade outing and gives Rory the lay of the land and her big scoop for the Yale Gazette. “You Jump, I Jump Jack” is one of my all-time favorite episodes, and it makes every Jess stan question their allegiance.  

7. Season 4, episode 9: “Ted Koppel’s Big Night Out”

Richard and Emily Gilmore in 'Gilmore Girls' season 4, episode 9, wearing Yale attire
(The WB)

GO YALE! What’s more autumnal than tailgating at a college football game? NOTHING! Emily (Kelly Bishop) and Richard Gilmore (Edward Herrmann) bring a campervan to Yale for the Harvard v. Yale football game, and no one’s more shocked by the atmosphere than Lorelai. This episode has marital problems, drinking, and surprise guests! 

6. Season 3, episode 6: “Take the Deviled Eggs”

Luke, Lorelai and Rory at a town meeting in Gilmore Girls
(The WB)

An emotionally complicated episode for Lorelai and Rory: Christopher, Rory’s father, is having a baby with his girlfriend, Sherry (Madchen Amick). Sherry invites Rory to her baby shower, who drags Lorelai along. Jess (Milo Ventimiglia) gets a new car and parks it in a highly public spot for everyone in Stars Hollow to cringe over when they think back to the events of season 2 (Rory broke her arm in a car accident when Jess was driving). In a fit of pent-up emotion, Lorelai and Rory throw leftover deviled eggs from Sherry’s baby shower at Jess’s car. 

5. Season 2, episode 5: “Nick & Nora/Sid & Nancy”

Rory Gilmore and Jess during their first meeting in 'Gilmore Girls'
(The WB)

This episode jumpstarts every diehard Gilmore Girls fan’s crush on Jess! The ecstatic feeling of September with a fresh semester and a new crush is the giddy feeling “Nick & Nora/Sid & Nancy” provides. Luke (Scott Patterson) is stumped when his troubled teen nephew appears at his door, and Lorelai steps in to help smooth things over. However, like every other teenage girl, Rory is a sucker for the bad boy, but mostly because his quiet and gripping intelligence matches her own. 

4. Season 1, episode 5: “Cinnamon’s Wake”

Sookie and Lorelay in Luke's Diner in the episode "Cinnamon's Wake"
(The WB)

The death of a pet is always heartbreaking, and “Cinnamon’s Wake” showcases Lorelai and Rory’s neighbor Babette’s (Sally Struthers) cat’s sad farewell. The setting and spirit of this episode are quintessential autumnal, as are most of Gilmore Girl’s first-season vibes. Rory has an embarrassing meet-cute with Dean, Lorelai confesses her feelings to Max (Scott Cohen), and the inn has a French crisis. 

3. Season 1, episode 6: “Rory’s Birthday Parties”

Rory's Sweet Sixteen birthday party in Gilmore Girls
(The WB)

This is an incredible and ICONIC episode packed with fun! It’s Rory’s BIRTHDAY, and she’s bombarded by having two parties. Emily Gilmore insists on throwing a fancy soiree at the Gilmore residence. She invites some of Rory’s classmates from Chilton in a horridly out-of-touch display of wealth while Lorelai throws the sweet 16 every small-town kid dreams of with all the playfulness one can get without seeming immature. This episode is also home to the TikTok viral line, “I am an Autumn,” as first said by Richard Gilmore.

2. Season 3, episode 9: “A Deep-Fried Korean Thanksgiving”

Rory and Lorelai Gilmore sit outside during Thanksgiving in Gilmore Girls
(The WB)

In true Lorelai Gilmore fashion, this mother-daughter duo has signed up for as many Thanksgiving dinners as possible. Sookie (Melissa McCarthy) must watch from the sidelines as her husband deep-fries a turkey she would have lovingly basted. Rory’s #1 bestie, Lane Kim (Keiko Agena), has her first kiss with Dave Rygalski, AKA Adam Brody, AKA Seth Cohen. Lorelai discovers that Rory applied to Yale, not just Harvard, and Kirk (Sean Gunn) is … being Kirk. 

1. Season 4, episode 22: “Raincoats and Recipes”

Dean and Rory in Gilmore Girls, "Raincoats and Recipes"
(The WB)

Possibly one of the best-crafted episodes of the entire series, “Raincoats and Recipes” has every quirk and charm of Gilmore Girls with the added sophistication of being in a later season. At the opening of the Dragonfly Inn, having invited friends and family to stay as a test run, all your favorite townies and relatives are under one roof for this spectacular rollercoaster. Lorelai and Luke share their first kiss on the steps outside; a naked Kirk shines white as a ghost under the moonlight, and Richard and Emily behave like children. However, if you aren’t satisfied with how chaotic this episode is, the final 5 minutes when Rory makes a catastrophic mistake will shake you to your core.


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Isobel Grieve
Isobel Grieve is a Freelance Writer for The Mary Sue. She scours the internet for culture, controversies, and celebrity News, and when she isn't writing about that, she's deep-diving into books, TV and movies for meaning and hidden lore. Isobel has a BAH in English, Cinema and Media Studies, and she has over two years of professional writing experience in the Entertainment industry on the Toronto Guardian, TV Obsessive, Film Obsessive, and InBetweenDrafts. You can read her unfiltered thoughts on Twitter @isobelgrieve