The Best Cozy and Classic Fall Movies to Watch

A quintessential fall rom-com, When Harry Met Sally is filled with crisp New York City scenes, golden leaves in Central Park, and plenty of cozy knit sweaters. Just typing this out is making me want to be in New York for the fall! It follows the relationship between Harry and Sally as they navigate friendship, love, and the question of whether the two can ever truly mix. It has banter, it has heartfelt moments, and it has an iconic soundtrack! So… it’s pretty much the perfect movie to curl up with when the air starts to cool.

2. Matilda (1996)

Matilda is full of magic (and good music). It’s the kind of cozy movie that feels perfect for a chilly day indoors. It’s the film adaptation of a Roald Dahl story about a gifted girl and her not-so-great family. Filled with colorful characters and lighthearted humor (but balanced with deeper themes of resilience) it’s great for kids and adults alike. If you’ve never seen it, it’s a must watch! It’s also filled with classic scenes…such as the infamous chocolate cake…IYKYK.

3. Dead Poets Society (1989)

Few films embody the spirit of fall like Dead Poets Society…we’re talking ivy-covered boarding school, candlelit rooms, and scenes of poetry under autumn trees. This story about an unconventional English teacher and the students he inspires is both heartwarming and bittersweet. It’s perfect for when you’re in the mood for something thought-provoking that still feels tied to the fall season. If you love stories about mentorship, creativity, and following your passions, this is a must-watch!

Ok, so Twilight might not be your typical cozy fall film, but it’s undeniably become a classic. The movie radiates moody, autumnal vibes with its misty forests, overcast skies, and the cozy Pacific Northwest setting. Between the back-to-school energy, small-town charm, and vampires, it’s giving major fall feels. There’s just something about it that makes it perfect for a seasonal rewatch. And honestly, if you’re up for a marathon, you can dive into the entire series! But I have to say there’s something about the very first film that makes it especially perfect for an autumn evening.

A romantic drama with a touch of witchy magic, Practical Magic is ideal for when you want something cozy but with a bit of enchantment. The film follows two sisters navigating love, family, and a generational curse, all set in a charming seaside town with moody fall aesthetics. And in case you needed another reason to watch it, it stars Sandra Bullock and Nicole Kidman. I actually just watched it for the first time last year, and it will definitely become a yearly rewatch for me. Plus, they’re coming out with a Practical Magic 2 soon…ish.

Few films capture the cozy, bookish spirit of fall like You’ve Got Mail. With its backdrop of New York in autumn…we’re talking pumpkins on stoops, bookstores with twinkle lights, and walks through leaf-strewn streets, this romantic comedy is both nostalgic and comforting. It’s endlessly rewatchable, with warmth that feels like catching up with an old friend. If you love a good rom-com with cozy city vibes look no further. Plus it has Tom Hanks and Meg Ryan. Need I say more?

Wes Anderson’s Fantastic Mr. Fox is practically autumn in film form with its golden color palette, cozy woodland settings, and quirky yet heartwarming story. The stop-motion animation gives it an extra layer of charm, making it perfect for a crisp fall evening. It blends wit, whimsy, and nostalgia in a way that feels like storybook magic come to life. Also the plot is literally, “Mr. and Mrs. Fox live a happy life until Mr. Fox slips into his sneaky, old ways and plots the greatest chicken heist the animal world has ever seen.” Like tell me you don’t want to watch that?!

A nostalgic classic fall movie, Halloweentown delivers cozy, magical vibes with its quirky costumes, charming small-town feel, and warm themes of family and belonging. It’s a must-watch (I watch it every single year) for anyone craving a lighthearted trip back to childhood Halloweens. This Disney Channel gem has an irresistible mix of adventure and heart that feels timeless…and the setting, UGH. It’s so good. And so Halloween-y. It’s a classic for a good reason There’s actually 4 movies total in the film series, but the first movie is the best (in my opinion) and can be watched as a stand-alone film.

Sweet, spooky, and a little nostalgic, Casper blends lighthearted fun with heartwarming moments. Set in a haunted mansion, it’s a story about friendship and belonging, it’s a great pick for when you want a Halloween-adjacent movie that’s cozy rather than scary. It strikes the perfect balance between cute and spooky, making it accessible for all ages. I think it’s such a sweet movie and enjoy watching it every year, especially as it gets closer to Halloween as it does have a more spooky element (even though it’s definitely not scary!).

Set against the backdrop of Boston, Good Will Hunting captures the charm of the city in the fall. The film follows Will, a math prodigy working as a janitor, as he begins to untangle his past with the help of a compassionate therapist. It’s about love and friendship and healing, making it an introspective and inspiring pick for cozy autumn nights! It’s just an overall good film with great characters (and great actors).

This short but timeless special is as cozy as fall gets. I think it’s a must watch for everyone at least once during the autumn season – even if it’s just playing in the background! With its pumpkin patch scenes, simple yet nostalgic animation, and endearing characters, it instantly transports you back to childhood. Watching it each year feels like a seasonal ritual, one best enjoyed with a blanket and a cup of hot cocoa.

An October staple, Hocus Pocus is playful, campy, and filled with Halloween spirit. From the cobblestone streets of Salem to the mischievous Sanderson sisters, this film embodies the fun of spooky season without being too scary. It’s the ultimate nostalgic watch for millennials and Gen Z, filled with quotable lines and silly fun. Plus, they just came out with Hocus Pocus 2 in 2022. And honestly for a remake I think it was done pretty well!

Whether it’s the feasts in the Great Hall, Quidditch matches in the crisp air, or the cozy common rooms, the Harry Potter films embody seasonal magic. Though they span the whole year, the autumnal vibes of Hogwarts… magic, broomsticks, flickering candles…make them a fall favorite. Watching them feels like entering a world where cozy and magical go hand-in-hand.