Fall is the season for rewatching what lasts. From Halloween with my son to the golden glow of When Harry Met Sally and the timeless lessons of Dead Poets Society, these are the movies that make autumn feel complete — and the ones I want my kids to carry with them.
The air is getting crisp, the days are getting shorter, and everything suddenly tastes like pumpkin spice. That is the season’s way of reminding us to slow down, grab a blanket, and settle into the comfort of movies we have seen a dozen times before. For me, fall is not about what is new. It is about rewatching what lasts.
When my kids were little, three or four years old, I wanted them to grow up on the right music before the tides of “cool” swept them away. We listened to the Beatles, not because they were trendy, but because they were great. The same idea carried over to movies. I did not wait for them to stumble into greatness on their own. I wanted to hand it to them early.
As they grew, the list shifted. By the time my son was ten, we watched Jaws together and he loved it. Now he is twelve, old enough for more mature themes and eager for scary movies, though not too scary. We have had to turn some off. That has become part of the fun, exploring together, finding out what sticks, and making these rewatchables our fall traditions.
Here is my lineup of fall rewatchables, movies that carry the crisp air, the golden leaves, and the kind of staying power worth passing down:
Halloween (1978) – the definitive October scare, now a father and son ritual in our house.
When Harry Met Sally (1989) – New York at its most golden and cozy, wrapped in wit and romance.
Moonstruck (1987) – big bowls of pasta, family arguments, and chilly Brooklyn nights.
Dead Poets Society (1989) – autumn in New England, poetry, and the courage to seize the day.
Good Will Hunting (1997) – Boston in the fall, full of second chances and hard won wisdom.
Fantastic Mr. Fox (2009) – Wes Anderson’s stop motion quilt of oranges and browns, clever and warm.
Remember the Titans (2000) – football under the lights, small town energy, and the hope of coming together.
These are not just movies I watch again every fall. They are part of how I remind myself, and show my kids, that greatness in art has a kind of permanence. Just like the Beatles, these films outlast fashion. They make the season richer, year after year.
Movies have always been a way for me to pass something on. When I wanted to share my love for baseball, we watched The Sandlot and The Bad News Bears. When I wanted them to know me better, I showed them Forrest Gump, a movie I love for its unbridled optimism. When I wanted to show them what cool really looked like, we sat down for Ferris Bueller’s Day Off. I wrote more about that spirit of youth and movies here.
Rewatching movies in the fall is not only about tradition. It is about memory, meaning, and passing down the kind of stories that stay with you long after the credits roll.
On my September 23 walk, the forest announced its changes loud and clear — walnuts thudding down in a mast year, mosquitoes in last-call mode, pawpaw perfume gone, and late-blooming smartweed still holding on. These abundance signals remind me that the woods don’t whisper their shifts; they proclaim them.
A walk through the woods brought me face to face with an owl, the call of a flicker, the sweet scent of pawpaws, and the rhythm of hollow logs. Sometimes the forest carries you, and all you can do is listen.
We moved to the DMV thinking we were immune to allergies. Four years later, we were congested, cranky, and armed with a four-step plan to stop sinus infections in their tracks.
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