BIGWORDS Movie COOLection: Best Movies To Watch In Fall

We’ve hit that point in autumn where activities like apple picking aren’t really seasonal anymore and we’re more likely to hunker down in our heated homes. As we trade the great outdoors for quieter days inside, nothing beats spending a rainy fall day curled up on the couch with a nice cup of tea and great flick. Below is a list of seven of our favorite movies set in fall that you should put in your Netflix queue for the next dark and chilly day. And, even better, all of the movies listed below are available through BIGWORDS, should you decide that one of them is a “keeper.”


When Harry Met Sally

When Harry Met Sally

Sure, this movie technically spans several seasons – and years – but its shots of fall are by far its most memorable scenes. From Meg Ryan’s perfect 80’s wardrobe of blazers and hats to the vibrant leaves in Central Park, the film perfectly captures fall in New York City through the eyes of a not-so-platonic pair of friends.


Sweet November


Feel like crying? Then Sweet November is the fall film for you! Nelson meets Sara, a quirky, spunky woman who takes a different man under her wing each month and shows him how to live a full, fun and meaningful life. Predictably, Nelson falls in love with Sara, who he discovers only keeps men around for a month at a time because she’s dying and doesn’t want anyone to get attached to her. Break out the tissues!


Autumn in New York


Included in most “best movies set in fall” lists, Autumn in New York is not unlike Sweet November – man falls in love with free-spirited woman diagnosed with a terminal illness. However, there’s a (kinda creepy) twist. The woman is the 22-year-old daughter of an ex-girlfriend of her much-older paramour. Strange though that might sound, Richard Gere and Winona Ryder make this a movie worth watching.


Good Will Hunting


No matter what other accolades Matt Damon and Ben Affleck rack up throughout their careers, they’ll always be known for the film that started it all for them. The Academy Award-winning movie perfectly captures fall in Boston with its combination of chilly weather, vibrant colors and cityscape.


Planes, Trains and Automobiles


A light comedy more your scene? Then check out this classic starring Steve Martin and the late John Candy as they spend a mishap-filled three days trying to get from New York City to Chicago for Thanksgiving.




Don’t worry – we have one for the film majors out there, too. Wes Anderson’s classic Rushmore follows the lives of an eccentric, precocious student, a beautiful, widowed teacher, and a selfish millionaire throughout the first semester of the school year. In classic Anderson fashion, the movie has become both a critical darling and a cult favorite.

Legends of the Fall


This epic drama, based on a novel by Jim Harrison, covers decades in the lives of sons Tristan, Samuel and Alfred Ludlow, sons of a retired military man (Hopkins). Devastating war scenes, a love TRAPAZOID and personal grief keep our tears flowing until the bitter end of the film, but there are many positive notes as well, that help land this film in our DVD collection. It’s timeless, cinematically gorgeous and Brad Pitt’s memorable water-droplet-white-smile-hat-tipping scene that cemented his place in the heartthrob hall of fame never hurt anybody.


Still not satisfied? Check out a few more of our fall favorites:



You’ve Got Mail

Dead Poet’s Society

Hannah and Her Sisters

Garden State