Fall Head Over Heels: 25 Enchanting Movies Showcasing East Coast Beauty in Autumn

When Harry Met Sally

The East Coast is the most beautiful place to be when summer ends and fall begins, as the trees turn to spectacular shades of red, orange, and yellow and the air takes on a brisk chill. Experience the beauty and coziness of an East Coast fall with these 25 movies, from chilling horror films to adorable rom-coms to playful kids’ movies.

1. Autumn in New York (2000)

Autumn in New York 2000 Metro Goldwyn Mayer Studios MSN e1693694185883
Image Credit: Metro Goldwyn Mayer Studios.

Well, the name of this one fits the category perfectly. It’s a love story about an older man who falls for a free-spirited woman half his age. Their love affair is an intense whirlwind of intimacy and passion, but their relationship only lasts for one autumn season. The film offers a unique look at love and brief affairs and how they can be beautiful.

2. Hocus Pocus (1993)

Bette Midler in Hocus Pocus
Image Credit: Buena Vista Pictures Distribution.

Hocus Pocus is one of the best kids Halloween movies of all time. It’s about three kids who accidentally awaken three witches in Salem who have been imprisoned for the last century. It’s a wacky and wonderful film that will enchant you from the first scene, and you’ll be wholly invested in the spooky plot.

3. Good Will Hunting (1997)

Good Will Hunting Matt Damon
Image Credit: Miramax Films.

Good Will Hunting is a powerful movie about a young man with an amazing brain but no opportunities to reach his full potential. He works as a janitor at a prestigious school in Boston. He miraculously solves an unsolvable equation, eventually being taken under the wing of a professor, Robin Williams, with a traumatic past.

4. Dead Poets Society (1989)

Robin Williams and Dylan Kussman in Dead Poets Society (1989)
Image Credit: Touchstone Pictures.

Another Robin Williams film that will move you in many ways is Dead Poets Society. It takes place in Delaware and tells the story of a class of students whose lives are changed by their passionate and eccentric teacher. The film explores traditions surrounding education and has a lovely autumn aesthetic.

5. Mona Lisa Smile (2003)

Mona Lisa Smile (2003)
Image Credit: Sony Pictures Releasing.

Mona Lisa Smile follows several young women attending Wellesley College in Massachusetts in the 50s. The dramatic film shows these women's different paths and how difficult it was back then to break traditions and subvert expectations. Many themes of feminism and self-discovery are still relevant and moving today.

6. Clue (1985)

Image Credit: Paramount Pictures.

Clue is a campy murder mystery in an extravagant and spooky New England mansion on a cold, stormy night. A mysterious, unknown host invites Guests to a dinner party, and secrets quickly spill. It’s based on the classic board game and has an unforgettable quirky, over-the-top vibe.

7. Practical Magic (1998)

Sandra Bullock and Nicole Kidman in Practical Magic (1998)
Image Credit: Warner Bros.

Practical Magic is a brilliant fall movie if you love witches and magic. It takes place in Coupeville, a fictional town on Whidbey Island off the coast of Massachusetts. Sandra Bullock and Nicole Kidman star as sisters who have very different goals in life but share the ability to practice magic, but sometimes don’t use it wisely.

8. Silver Linings Playbook (2012)

Silver Linings Playbook, Chris Tucker
Image Credit: The Weinstein Company.

Silver Linings Playbook is set in Ridley Park, Pennsylvania, during football season. Bradley Cooper and Jennifer Lawrence star as two people battling mental illnesses and trying to get their lives back on track. It’s an emotional and poignant movie with sensational performances.

9. The Village (2004)

The Village e1693694568119
Image Credit: Touchstone Pictures.

For something extra spooky that will leave you unsettled, watch The Village, a mysterious thriller and horror movie set in the 19th century in Pennsylvania. The small community is terrorized by monsters who live in the woods near them, but their fears are misplaced.

10. Girl, Interrupted (1999)

Girl, Interrupted (1999)
Image Credit: Columbia Pictures.

This intense film is about a young woman who is committed to an institution after she tries to take her own life. She meets some other women struggling with mental health, and they bond over their problems and the discomfort they feel in the New England asylum.

11. Knives Out (2019)

knives out
Image Credit: Lionsgate.

Knives Out is one of the most popular and successful modern whodunits, with a star-studded cast. The movie mainly occurs at Ames Mansion, a 1920s home south of Boston in Borderland State Park. The film is a wild ride and captures the beauty of a chilly fall day in New England.

12. The Social Network (2010)

The Social Network Movie (2010)
Image Credit: Merrick Morton/ Columbia Tristar Marketing Group.

The Social Network is a gripping movie about the invention of Facebook and subsequent drama surrounding ownership rights. Most of the movie's first half takes place at Harvard University, showcasing the cozy and calm aura of Boston in the fall season.

13. Sleepy Hollow (1999)

Sleepy Hollow (1999)
Image Credit: Summit Entertainment.

This film, based on classic folklore, takes place in New York City at the end of the 18th century. Sleepy Hollow is a small town plagued with gruesome murders, and Ichabod Crane is sent to investigate and help the people. It has that spooky fall vibe that makes it the perfect Halloween watch.

14. When Harry Met Sally (1989)

When Harry Met Sally
Image Credit: Castle Rock Entertainment.

When Harry Met Sally is one of my favorite romances, taking place in hectic New York City. The film stars Meg Ryan and Billy Crystal as two friends who slowly fall for one another over a few years. While the movie is not set in fall, some of the sweetest scenes are of them walking around on autumn days.

15. The Royal Tenenbaums (2001)

The Royal Tenenbaums Gene Hackman
Image Credit: Buena Vista Pictures Distribution.

The Royal Tenenbaums is a Wes Anderson movie about a wealthy family and three eccentric children. Like all Anderson films, it’s quirky in the best ways and has a gripping plot. It’s set in New York City, and most of the film takes place in autumn, with the characters wearing jackets and enjoying the crisp air.

16. The Scarlet Letter (1995)

The Scarlet Letter (1995)
Image Credit: Buena Vista Pictures Distribution.

The Scarlet Letter is the film adaptation of Nathaniel Hawthorne’s novel of the same name. It’s set in the Massachusetts Bay Colony in the 1660s and tells the story of a woman cast out of the community for adultery. The movie offers beautiful autumn scenery amidst the distressful and tragic story.

17. Fever Pitch (2005)

Fever Pitch (2005)
Image Credit: 20th Century Fox.

Fever Pitch is an adorable rom-com I haven’t seen in a few years, but it will always have a special place in my heart. It’s about a Red Sox fanatic who begins putting his favorite baseball team over his girlfriend. It takes place during baseball season in Boston, one of my favorite times of the year. 

18. Casper (1995)

Image Credit: Universal Pictures.

Casper, the movie about the friendliest ghost, takes place in a town called Friendship, Maine, in a stunning but eerie mansion. This film is the perfect choice for family movie nights when the spooky season is approaching in fall. The movie is adorable and whimsical, with the right amount of paranormal fun.

19. The Cider House Rules (1999)

The Cider House Rules (1999)
Image Credit: Miramax Films.

Unlike Casper, I cannot describe The Cider House Rules as a jolly or fun movie. On the contrary, it’s pretty depressing and tragic. It takes place in a few locations along the East Coast, including Massachusetts, Maine, Vermont, and New Hampshire, following a young man through all the seasons.

20. Julie & Julia (2009)

Julie & Julia (2009)
Image Credit: Sony Pictures Releasing.

Julie & Julia doesn’t have many scenes that take place outside, as the leading ladies are always in the kitchen making culinary magic. However, you do get to see Julie coming and going from her tiny NYC apartment in all the seasons as she cooks her way through Julia’s book.

21. The Trouble With Harry (1955)

The Trouble with Harry (1955)
Image Credit: Paramount Pictures.

This film is set in Vermont during fall, in a lovely little town with a tight-knit community. One day, a man is found dead on a hillside, and no one knows what happened, but many residents begin to suspect themselves. This comical mystery has a charming, folksy vibe that captures New England's fall spirit.

22. Little Women (2019)

Little Women
Image Credit: Sony Pictures Releasing.

Another folksy movie that will make you feel cozy is Little Women, a phenomenal film packed with complex emotions. It’s set in Concord, Massachusetts, and tells the stories of Meg, Jo, Beth, and Amy. There are romantic exploits and plenty of drama surrounding the four sisters, who support each other through everything.

23. The Witch (2015)

The Witch
Image Credit: A24.

The Witch, sometimes written as The VVitch, is about a family outcast from their community in New England. They live alone on their rural land, and when strange things happen around their property, they turn on one another. It’s a chilling and frightening movie that has a sensational ending.

24. You’ve Got Mail (1998)

You’ve Got Mail Meg Ryan Tom Hanks
Image Credit: Warner Bros.

You’ve Got Mail is a romantic comedy starring Meg Ryan and Tom Hanks, one of the most iconic rom-com duos ever. It’s set in New York City, prominently in autumn, and follows the progression of their complex love story. It’s a charming film with a cozy feeling that is perfect for a lovely fall day.

25. Beetlejuice (1988)

Beetlejuice (1988)
Image Credit: Warner Bros.

Beetlejuice is a classic Halloween movie about a young couple who suddenly die and become ghosts haunting their house. When a new family moves in, the couple does everything possible to get them out, even turning to the demon-like creature called Beetlejuice. The story takes place in Winter River, Connecticut, starting at the end of summer and going into fall.

Source: (Reddit).

Author: Veronica Booth

Title: Freelance Writer

Expertise: Food, Entertainment, Movies, TV, Fashion, Lifestyle, Celebrity


Veronica is a food, fashion, and entertainment writer from Boston, MA, with a passion for all things lifestyle and culture. She graduated from Boston University in 2019 with a bachelor's in English literature. From Anna Wintour to Angelina Jolie to Alton Brown, she has her finger on the pulse of all things Hollywood and celebrity.

If she's not in the kitchen crafting new recipes, then she's binging the latest HBO series and catching up on the hottest trends in Vogue.

She has written for and been syndicated by publications like The Weather Channel, The Daily Meal, The Borgen Project, The Good Men Project, The Express, MSN, Wealth of Geeks, and Not Deer Magazine. Her writing experience ranges from global news articles to celebrity gossip pieces to movie reviews to homemade recipes and more.