Staff Recs: What to Watch Transitioning From Fall to Winter

A young woman wearing a green sweater, jeans and a jacket lies on green grass, surrounded by fallen leaves. She is clearing the leaves around her arms by moving them back and forth, smiling on a sunny day.
Alma junior Bonnie Lord makes a leaf-angel on the quad. Though this is often done with snow, the time between fall and winter is a time for the unusual (Photo illustration courtesy of Abby Dombrowski).

When the Pleiad isn’t getting the scoop on voting accessibility and campus costume contests, we’re appreciating our favorite movies and TV shows

But what about this season, the nebulous time between Halloween and the winter holidays? 

Below you will find a collection of media recommendations from members of our staff, answering that very question.

Editor-in-Chief, Bella Bakeman

I am a lover of fall, but I struggle to enjoy the season after Halloween has passed. I sort of hate Thanksgiving, in concept and practice. And, since my grandpa died, I haven’t been able to stomach holiday movies. However, I am a lover of what I feel are quintessential movies and shows: the fall dramas.

Favorite Fall Transition Movies:

“When Harry Met Sally” (1989): I watched this movie for the first time last year and felt the warmth of fall from start to finish. It’s a classic, it has that scene in it and all of the characters dress head-to-toe in the fall fits.

“You’ve Got Mail” (1998): Maybe it’s the boutique bookseller going up against the corporate bookseller, maybe it’s the sweaters Meg Ryan’s character wears or maybe it’s watching adults fall in love over email – but I am obsessed with this movie. Another Meg Ryan classic, this movie is less fall-centered than “When Harry Met Sally” but something about it just makes me feel like curling up on the couch with some warm apple cider and popcorn. 

Good Will Hunting (1997): If you’ve yet to see this classic film, take this as your opportunity. The cast is stacked, the scenery is stellar and the dialogue is superb. That’s it, that’s my pitch. Watch it.

Favorite Fall Transition Shows:

“Gilmore Girls” (2000-2007): I’ve already recommended this show at least once, but I like to specifically watch the Thanksgiving and fall episodes this time of year. My favorite is “A Deep-Fried Korean Thanksgiving” where the Gilmore girls attend four separate Thanksgivings. An honorable mention: “Ted Koppel’s Big Night Out,” where the Gilmore girls tailgate at the Yale v.s. Harvard game.

The Friends Thanksgiving Episodes: There are quite a few, and my favorite is the football episode, Monica’s need to win is just too relatable. My ranking in order from best to least best: “The One With the Football,” “The One Where Ross Got High,” “The One With the Rumor,” “The One With All the Thanksgivings,” “The One With Rachel’s Sister,” “The One With Chandler in a Box,”  “The One Where Chandler Doesn’t Like Dogs,” “The One Where Underdog Gets Away,” “The One With the Late Thanksgiving” and finally “The One With the List.”

“A Charlie Brown Thanksgiving” (1973): God I love this Charlie Brown special, it’s cute, heartwarming and to me, a beautiful depiction of chosen family.

Managing Editor, Bonnie Lord

I am of the opinion that there are Thanksgiving movies, despite what some might say. Along with these films, this time should be spent watching the last of the scary movies, and preparing for the cold months with the comforts of nostalgia. It’s far too soon for Christmas movies, and a little late for many horror movies – it is what is known as “curl up on the couch and rewatch” season. 

Favorite Fall Transition Movies:

“Home for the Holidays” (1995): This is THE Thanksgiving movie. Holly Hunter and a young Robert Downy Jr. absolutely steal the show, and bring both true emotional weight and surprisingly dorky humor to this film. If you have siblings, watch this. Trust me, they capture the bizarre energy between siblings better than most films.

“Juno” (2007): This movie captures the aimless, creeping nostalgia of the season perfectly. The cinematography is inspired, the humor is surprisingly modern, Elliot Page and Michael Cera have incredible chemistry and the soundtrack is amazing. Not to mention, what other film can claim to have a soundtrack full of  Kimya Dawson? Not many, and that’s what really brings this film to life. 

Favorite Fall Transition Shows:

“The X Files” (1993-2018): The genuine terror I feel when I watch this show is something not often captured in modern suspense shows. The classic, bitter chemistry between Mulder and Scully, the way it’s somehow always just about to be winter and the incredible special effects give this show something intangible and perfect for the season, especially in its first few seasons.

“Scooby Doo, Where Are You!” (1969-1978): Doesn’t watching old Scooby-Doo just bring you the joy of a Saturday morning? For me, I remember watching our DVDs of the show when the power would go out on our tiny-screened personal DVD players we used for long car rides. It’s spooky, silly and nostalgic, and it’s before later versions of the show ruined Velma.

Features/Opinions Editor, Jocelyn Kincaid-Beal

This time we find ourselves in currently is certainly too early for Christmas movies. I am a firm believer that the Christmas season starts the day after Thanksgiving. I’m a fan of horror movies all year round, but I think November is also a time for dramas – movies about love, grief, all those things. 

Favorite Fall Transition Movies:

“Little Women” (2019): This movie is full of beautiful cinematography, and has beautiful moments from every season, but I think its most iconic scenes take place in fall and winter. In addition to all the cozy vibes and amazing fall and winter outfits, “Little Women” tells a story of family dynamics and relationships that I think a lot of us can relate to, especially around the holidays. 

“Dead Poets Society” (1989): It’s fall at the beginning of this movie, and winter by the end, so I think it makes perfect sense on this list. It follows a group of teenagers through their first semester at a boarding school, so the changing of seasons is also thematically important. 

I love this movie very much, but I should warn you that I sobbed when I watched it. 

“Fantastic Mr. Fox” (2009): The aesthetic and color scheme of this movie are so beautifully fall. It’s also clear that the weather’s getting colder, and the world is slowing down, giving the feeling that it’s time to gear up to hibernate. 

This movie has impeccable themes, dialogue and celebrity voice-performances. It has also been known to make me cry.

Favorite Fall Transition Shows:

“Over the Garden Wall” (2014): This is the ultimate fall show. My god I love it so much. It’s so whimsical and silly, and the fall vibes are just radiating from it. It’s not a spooky show, so I think October is too early to watch it – but now’s the perfect time!

“Gravity Falls” (2012-2016): This one has kind of similar vibes to “Over the Garden Wall,” but sillier and less inherently fall, I would say. It canonically takes place in the summer, but the creepy “something’s not right about this place” feeling throughout the show makes it an honorary fall show in my mind.

Assistant News Editor, Heidi Faramelli

Honestly, if I could only choose one season to live in for the rest of my life, I’d choose fall. It’s spectacular in so many ways – beautiful leaves changing, hot apple cider on cool days and pumpkin patches on warmer ones – but one of my favorite things about it is the cozy media it provides.

Favorite Fall Transition Movies:

An often-forgotten Thanksgiving movie I love is “Planes, Trains and Automobiles” (1987), a comedy about a man trying to get home to spend the holiday with his family. Plus, can you really go wrong with the Steve Martin and John Candy combination?

I have to remention “When Harry Met Sally” (1989) because it is the perfect movie for both fall and winter. I also love “Edward Scissorhands” (1990), “It’s the Great Pumpkin, Charlie Brown” (1966), “Coco” (2017), “James and the Giant Peach” (1996) and the Harry Potter movies (2001-2011) – particularly the first three because they’re more wholesome, but four through seven definitely have an eerie vibe if you’re looking for that. 

Favorite Fall Transition Shows:

“A Series of Unfortunate Events” (2017) is one of my favorites – it’s spooky and great for the fall season. Also, “Dawson’s Creek” (1998-2003) is a show with fall vibes that I love but haven’t finished yet. And, could I really close this out without mentioning the most iconic fall t.v. show of all time? “Gilmore Girls” (2000-2007) is currently being watched by me daily, and as I work on homework, I’m daydreaming about stopping into Stars Hollow Books and grabbing coffee at Luke’s. 

Photographer, Lizzy Kelley

Personally, I’m not into all the rom-com movies that tend to pop up in the winter era, so I stick with horror movies. I think that horror movies when the weather is starting to get colder as we transition into winter are the best. I try to prolong the Halloween season as long as I can.

Favorite Fall Transition Movies:

“The Nightmare Before Christmas” (1993): This is my all-time favorite transition movie, I think that it kind of lets go of the Halloween stuff and starts to turn us towards the Christmas time movies.

“The Peanuts Movie” (2015): Is the only acceptable Thanksgiving movie out there. The people who say there are Thanksgiving movies are liars, it’s a hoax.

Photographer, Gabriela Popa

Since I hate scary movies (I’m trying to get into them a bit more), I just try to push through until Nov. 30, aka, the real start of Christmastime.

Favorite Fall Transition Movies:

“La La Land” (2016): I just love a good romance movie and to me, it’s a little bit of a horror movie because that end is SCARY! Emma Stone and Ryan Gosling are also just so iconic and can never make a bad movie together. 

“Scream” (1996): really the only Halloween movie I seek to watch. It’s the only “scary” movie I like because it’s predictable and can be watched even after Halloween. Overall great, and Ghostface is purely hilarious.

Favorite Fall Transition Shows:

“Gilmore Girls” (2000-2007): The whole series is just phenomenal, and I love it with all my heart. It really is just autumn vibes and even winter ones when the time comes. 

“Brooklyn Nine-Nine” (2013-2021): Though it’s not really an “autumn show,” I love the Halloween Heist episodes because they really show the precinct acting like a family but with a lot of competition. Also, a good comedy is just good for the soul. 

Staff Writer, Sophia Valchine

For me, fall transition movies mean stop-motion animation.

Favorite Fall Transition Movies:

“Coraline” (2009) is an amazing fall transition movie, especially closer to Halloween. As a kid I was too scared to finish it, but now I can appreciate the spookier elements and the overall vibe of the movie never fails to make me smile. 

“Corpse Bride” (2005) is also great for this time of year, and while the underworld may still have a Halloween feel, the dull gray world the living characters inhabit is still very beautiful and prepares me for the perpetual cover of clouds to come.

“Frankenweenie” (2012) finishes off my trio of stop-motion movies. Even though all three of these movies have wild and silly concepts, they all bring me comfort in their weirdness, and even though “Frankenweenie” is in black and white it still has lots of fun energy that I never get tired of each year. 

Favorite Fall Transition Shows:

“Over The Garden Wall” (2014) is my absolute favorite fall transition show. It’s very short and easy to watch in the background while I do homework and has so many cute little songs that help keep me going as the weather starts to get gloomy.

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