3 best fall episodes of Gilmore Girls that feel like a hug from Stars Hollow

When you think of the show and look at the online discourse, it's clear as day that Gilmore Girls and fall are basically besties. And honestly, Taylor Swift wasn’t wrong at all when she said, ‘Autumn leaves falling down like pieces into place’ because that’s exactly what it feels like when it’s time to return to the warm small town of Stars Hollow.

The moment the leaves start falling, the minute they turn orange and red, it's like Stars Hollow itself starts calling. There's something about the crisp, chilly air, thinking about the warm coffee mugs at Luke's, and Lorelai's never-ending banter that feels like you've wrapped yourself up in your favorite hoodie.

Gilmore Girls doesn't just show autumn — it quite literally is autumn. If you've ever dreamed of living in a town where everybody knows your name, then these 3 fall episodes are your ultimate comfort watch. They're the kind of episodes that make you want to slow down, sip a warm cup of hot chocolate, and stay in Stars Hollow forever.

Author's Disclaimer: These are just my favorite fall picks, and if there’s one thing I've learned from Gilmore Girls, it’s that there’s always room for more coffee and warm fall episodes. There are plenty of other autumn gems in Stars Hollow waiting to be rewatched, too!

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3 Gilmore Girls fall episodes that feel like a warm hug from Stars Hollow

1] “They Shoot Gilmores, Don’t They?” (Season 3, Episode 7)

There's no fall without the Stars Hollow dance marathon, is there?. "They Shoot Gilmores, Don't They?" is pure Gilmore Girls magic. It's chaotic, emotional, and full of heart. The entire town comes together dressed in vintage costumes, ready to dance till sunrise. The set design alone screams fall, from the amber lighting to the town square.

But this episode hits a little bit deeper than just warm fall nostalgia. It's THE episode when Dean finally breaks up with Rory, and Jess is finally able to make his way into Rory's life.

Between the heartbreak and warmth, this episode does capture the bittersweet side of autumn. You can almost smell the fallen leaves as Lorelai comforts Rory mid-sob on that very dance floor. Even with Kirk dancing around in triumph as he wins the competition, it's impossible not to feel that tug in your chest.

It's one of those Gilmore Girls episodes where the season itself becomes a character. It's beautiful, fleeting, and emotional. Perfect for your cozy fall re-watch.

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2. “Kiss and Tell” (Season 1, Episode 7)

If autumn in Gilmore Girls had a home, it would definitely be this episode. "Kiss and Tell" feels like the first real sip of fall. The pumpkins are out, the decorations are up, and Stars Hollow is glowing under its annual Autumn Festival.

Rory gets her first kiss from Dean at the supermarket, Rory steals a cornstarch box not knowing what to do after the kiss, and this episode might as well be the official start of every coming-of-age fall memory ever.

The magic isn't just in the romance, though. It's in Luke refusing to decorate his diner with paper turkeys, in Taylor's over-the-top enthusiasm for fall colors, and in Lorelai trying (and failing miserably) to keep her cool about Rory's dating life.

Every scene feels dipped in warmth, laughter, and the kind of small-town charm that made us fall for Gilmore Girls in the very first place. It's the coziest kind of chaos you'd expect from a show made in the 2000s. The kind of show that makes you want to live in a world where autumn never ends and coffee is always brewing at Luke's.

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3. “You Jump, I Jump, Jack” (Season 5, Episode 7)

This one's for the #TeamLogan fans who love their Gilmore Girls with a hint of adventure. "You Jump, I Jump, Jack" takes Rory out of Stars Hollow and takes her into the mysterious, elite world of the Life and Death Brigade, which, well, is Logan's wild playground.

Set against blazing autumn trees, Rory experiences a rush of excitement that feels like she's finally walking into a new season of her life. There's adventure, there's Logan Huntzberger, and there's fall. Couldn't get better than this, could it?

It's romantic, it's risky, and it's also a newer adventure for Rory. The golden tones of the forest, the crisp New England air, and that jump scene are what make this episode to be of my top 3 fall episodes to watch.

Logan represents everything unfamiliar and thrilling, pulling Rory out of her comfort zone. For a show rooted in cozy predictability, this episode is a beautiful shake-up.

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The best fall episodes of Gilmore Girls aren't just about pumpkins out in the street or about cinnamon coffee. They're about change. Whether it be a change in the air/the weather or a change in the lives of Lorelai or Rory.

"They Shoot Gilmores, Don't They?" "Kiss and Tell," and "You Jump, I Jump, Jack" each wrap you in the warm, familiar town of Stars Hollow, while reminding you that life keeps moving, just like the seasons. Watching them feels like returning to an old friend. A friend who always has a mug waiting for you at Luke's.

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Also read: How Gilmore Girls defined the early 2000s, and why it’s still so popular