- When Harry Met Sally (1989)
This fall favorite has been on my autumn movie list for a long time. When Harry Met Sally captures the cozy chaos of New York in the crisp season of fall. The witty banter and timeless chemistry in this movie prompt a timeless question: can men and women be friends? Meg Ryan and Billy Crystal carry razor-sharp dialogue and classic fall outfits that never go out of style. This movie always puts me in the fall mood, making me wish that I were living in the West Village, NYC, with the ability to walk Central Park on any ordinary fall afternoon.
- Little Women (2019)
Greta Gerwig’s Little Women is the cinematic equivalent of a candlelit evening with a good book and a cup of tea. The film weaves the March sisters’ stories with grace, color, and heart. Jo, Beth, May, and Amy have taught me so much about family, love, passion, and adventure. This movie makes you dream about a slow, family-filled life full of love and grace. It’s about sisterhood, dreams, and the bittersweet beauty of growing up; it’s perfect for a fall evening.
“Women have minds and souls as well as just hearts, and they’ve got ambition and talent as well as just beauty. And I’m sick of people saying love is all a woman is fit for”
Jo March
- You’ve Got Mail (1998)
If a pumpkin spice latte were a movie, it would be You’ve Got Mail. Set against a backdrop of fall in Manhattan, this charming rom-com pairs Meg Ryan (again!) and Tom Hanks as business rivals who unknowingly fall for each other online. Between bookstore charm, cozy cable-knit sweaters, and the nostalgic sound of a dial-up modem, this film feels like a love letter to both romance and the golden era of the internet.
- Serendipity (2001)
This movie follows two strangers who believe that fate will draw them together if they are “meant to be.” They meet by chance during the holiday rush in New York City, and they test destiny by writing their names in a book and a five-dollar bill, hoping the universe will reunite them if they’re destined for one another. It’s whimsical, a little magical, and full of cozy cityscapes that bridge fall and winter. It’s a perfect pick for believers in destiny.
- Two Weeks Notice (2002)
Sandra Bullock and Hugh Grant serve up peak early-2000s charm in Two Weeks Notice, a witty workplace romance about an idealistic lawyer and her delightfully clueless billionaire boss. Between their sharp exchanges and undeniable chemistry, the movie delivers all the feel-good, cozy chaos of a rom-com set in a crisp Manhattan fall. It’s polished, funny, and brimming with charm, making it a perfect wind-down watch after a long day.
Go watch a few fall movies!
All of these movies are just tastes of fall that transport you to the streets of NYC in autumn and make you fall in love again. These movies allow you to escape into a different world and dream again. These stories aren’t just movies; they’re little reminders that, even in the chill of autumn, love and hope are always in season.