Step Into Your Favorite Fall Movie By Visiting These US Towns
Summer and winter both have their fair share of fans and haters, but practically everyone has a soft spot for fall. Truly a transformative time of year, the world sheds itself of all baggage come autumn. This makes it the perfect time to pack up some of your own and travel to a picture-perfect destination — and what could be better than putting yourself in one of your favorite fall films? Hollywood may be known as the film capital of the world, but when it comes to fantastic fall films, some just have to be shot on location.
New England is a go-to fall destination, and naturally, there have been plenty of films set there that capture the beauty of the season. Other small coastal towns and major cities have their place in the fall film industry as well. From iconic Halloween destinations to unsuspecting towns with very real ties to cozy fall favorites, there are a handful of U.S. destinations that will make you feel as though you've (quite literally) entered your autumn comfort movie.
Salem, Massachusetts
If the United States had a Halloween capital, it would be Salem, Massachusetts. Steeped in legend and historical horrors, the Witch City has naturally been the setting of many spooky films, many of which were actually filmed there. The most famous of these is undoubtedly the cult classic, "Hocus Pocus," which had various filming locations in Salem that you can still visit.
The opening flashback scene where the Sanderson sisters originally put a curse on the town was filmed in Pioneer Village, which is a recreation of how pioneer Salem looked when the witch trials happened. Other historical locations like Old Town Hall and The Ropes Mansion were used for major settings and scenes and are located right in the heart of Salem. A walk through the witchy town is like a "Hocus Pocus" tour — you can even usually spot a few sets of Sanderson sisters wandering the streets as well.
A more modern, spooky-adjacent film to come out of Salem is Adam Sandler's "Hubie Halloween." The comedian's classic silliness is felt throughout the film, giving the town a refreshing sense of lightness in the crisp autumn setting. One of the only scenes to actually be filmed in the town involved the iconic Witch Museum, but the whole vibe of "Hubie Halloween" gives viewers an idea of what it'd be like to live in the Halloween-centric town without the stream of tourists.
St. Helens, Oregon
Any Disney kid who knows their stuff has seen the "Halloweentown" franchise and likely rewatches the first installment every autumn. The OG film was shot in St. Helens, Oregon, and the cute town transforms back into the fictional, friendly monster town every spooky season so that fans can feel like they're living inside their favorite '90s film.
St. Helens may look like your typical small town every other month of the year, but once Halloween season begins, it rolls out its oversized pumpkin centerpiece and becomes a place of wonder where creatures of all kinds are free to roam. If you want the full "Halloweentown" experience, plan to visit on a Saturday or Sunday when more attractions are open and the place is full of costumed fans doing their very best Marnie or Luke impersonations. Of course, Benny, the cab-driving skeleton, is present too.
It's not just "Halloweentown" featured in St. Helens — the town becomes an ode to the holiday in general. The small town may look the part of the classic Disney staple, but Halloween reigns supreme here with haunted houses, spooky oddities, and museums available to explore this time of year.
Sleepy Hollow, New York
Though the plot of Washington Irving's "The Legend of Sleepy Hollow" is purely fictional, the town is not. The movie based on the short story, unfortunately, was not filmed in Sleepy Hollow as the charming town doesn't quite capture the darkness of a Tim Burton flick, but the spirit of the legend is undeniably present in the town itself. At just a day's trip away from New York City, Sleepy Hollow is accessible for both local New Yorkers and those visiting from afar.
The town and its residents have fully embraced "The Legend of Sleepy Hollow" and its Headless Horseman antagonist as their mascot and, in a way, a large part of their personality. Images and statues of a headless man atop a horse holding a flaming jack-o'-lantern can be spotted throughout the town, and the story of his significance is told in many landmarks found here — the local high school's mascot even takes on the spooky character.
Visiting during autumn, though, really elevates any Sleepy Hollow experience. Crossing the cemetery's replica of the "Sleepy Hollow" bridge with the leaves falling all around and the gravestones in the distance is really quite a creepy experience. Is that the sound of beating hoofs in the distance, or just your mind playing tricks on you while in the mysterious Horseman's territory?
Rockport, Massachusetts
You may associate rom-coms with Valentine's Day, but the cozy vibes that autumn brings with it are perfect for cuddling up with a romantic movie. "The Proposal" isn't widely seen as a fall or a Thanksgiving movie, but maybe it should be. With an eccentric family at its center, it's the perfect film for the gathering holiday. Having been largely filmed in Rockport, Massachusetts, the town offers the same quaint small-town vibes as Ryan Reynolds' on-screen hometown.
Oddly enough, the romantic comedy is set in Alaska. While Rockport is undeniably a New England town, it actually did a wonderful job of impersonating an Alaskan one. Some of the same fall colors can be seen in the two far-off destinations, as well as rocky coastlines.
It's the small collection of shops and businesses, though, that really transport visitors into a scene from "The Proposal." Sandra Bullock and Ryan Reynolds' characters can be seen strolling by shops like the Rockport Fudgery, and following in their footsteps is the perfect way to kick off a fall vacation in New England.
New York City
NYC is a haven for film fans, so it's no surprise that a number of your favorite fall flicks were filmed here. Though the holiday season in New York outshines autumn, you shouldn't sleep on the Big Apple when the leaves start to turn. Probably the most iconic movie around this time of year that takes place in NYC is "Breakfast at Tiffany's," though there are plenty of titles that are nipping at its heels. The city has both come a long way and stayed remarkably the same in the 60-plus years since the film's release, and you can still visit a lot of the same places Audrey Hepburn's character did nowadays. Central Park, of course, is a must, as well as the Fifth Avenue flagship store for Tiffany & Co.
Other major motion pictures that show off the beauty of the Big Apple in autumn are romantic comedies "You've Got Mail" and "When Harry Met Sally." Both are classics that really only require a stroll around the city to replicate, and heading to Katz's Delicatessen will bring back memories of that famous pastrami scene that had both the world and Harry falling in love with Sally.
Another fall favorite is "Ghostbusters," a staple in October and one of the best family-friendly Halloween features ever. You may not have a ghostly encounter when visiting the New York Public Library or 55 Central Park West, but you'll hit the sweet spot on a real "Ghostbusters" NYC tour.
Boston, Massachusetts
Fall is when trees shed their leaves, and it is the perfect time for cinephiles to get in their feels and shed some tears. "Good Will Hunting" is an emotional movie, and nothing tops the emotion meter better than a psychiatrist Robin Williams breaking down a genius janitor Matt Damon. There are also some gorgeous fall shots of Boston in it as a consolation prize — how do you like them apples?
Though MIT is central to the plot, "Good Will Hunting" largely takes place in South Boston during the cozy autumn season. One specific location you shouldn't miss if trying to get the "Good Will Hunting" vibe right is the Boston Common, where the iconic bench where Damon and Williams' characters have their big movie poster moment is located.
With how transformative the film is for Will, autumn is an ideal time to visit some of his favorite haunts in person. Plus, Boston was labeled as one of "the world's most beautiful autumn cities," according to a study done by Premier Inn. So even if you have no emotional ties to "Good Will Hunting" but want to check out some of the best fall foliage the U.S. has to offer, Boston is the place to visit.
Coupeville, Washington
The cult classic film "Practical Magic" may be set in witchy New England, but it found a perfect filming location about 60 miles outside of Seattle in Coupeville, Washington. The town does a great job of disguising itself as a coastal area in the Northeast. The Victorian home that the witchy title is centered around is sadly not real, but there are other inclusions that you will immediately recognize in Coupeville.
The downtown area and Front Street give off major "Practical Magic" vibes, and you can still visit some of the shops featured in the movie too. A lot of the buildings are very much still there, making a stroll down the street feel as though you could be right beside Sandra Bullock and Nicole Kidman. (In spirit, at least.)
Thanks to "Practical Magic" putting the town on fall fanatics' radars, Coupeville holds a fall festival every year that makes it a great spooky destination to spend Halloween at. Pumpkin patches, parades, haunted houses, and more Halloween-centric events take place during the festival, making for great family fun.
Chicago, Illinois
There have been plenty of films shot in Chicago, and they're easy to spot thanks to the city's very recognizable cityscape. However, not many fall flicks can call the Windy City home, with "When Harry Met Sally" as one of the big exceptions. Harry and Sally's journey starts out at the University of Chicago, where you can visit to see some of the grand architecture featured at the beginning of the film.
While "Ferris Bueller's Day Off" is largely thought to be a spring film, the big parade scene is one that typically takes place right at the beginning of the fall season, making it indeed a perfect watch to jumpstart autumn. The Von Steuben Day Parade celebrates German culture in America and still takes place in Chicago every September.
Art museum montage, anyone? One of the best scenes in "Ferris Bueller's Day Off" is the delinquents' exploration of Chicago's most well-known art museum. Visit the Art Institute of Chicago to channel your inner Bueller and make an art montage of your own, all while seeing some of the most famous works of art in the world. Luckily, everything Ferris did on his day off is pretty exciting, making recreating it a worthy endeavor when visiting the big city.
Astoria, Oregon
A film all generations love to enjoy and hold dear to their heart, "The Goonies" is a classic fall staple. It's rare to find a real place that so wonderfully captures such a fantastic world. However, a great deal of the major scenes in "The Goonies" can be seen almost exactly as they were in the film, even almost 40 years later, in Astoria. While you likely won't strike gold, visiting one of the most adored films' inspired and shot locations is a treasure for fans all in itself.
Of course, the iconic beach scene with Haystack Rock in the background can be recreated at Cannon Beach — you'll just need to find yourself a treasure map first. This beach and the County Jail are two of the most recognizable locations you can visit near Astoria. The Goonies' house, as well as some other characters' houses, are located here. There are so many film locations here that exploring the coastal town is like playing a game of "The Goonies" search and find.
Mystic, Connecticut
You only have to go as far as Mystic, Connecticut for a slice of heaven. Julia Roberts' career kickstarter film "Mystic Pizza" was not only filmed largely in an area of the coastal town, but the central pizza shop from the film is actually a very real place that still exists. Entertainment Weekly calls "Mystic Pizza" "one of the fall-iest fall films of them all" and a "cozy-with-a-capital-C movie." So, if you're looking to be transported into a cozy fall world, look no further than Mystic, Connecticut.
The real-life town and pizza shop largely contribute to the homegrown, humble vibe that the classic flick has. "Mystic Pizza" makes you feel as though you could be involved in the characters' lives, and visiting the real place that inspired the film will make that feeling so much stronger. Since the movie blew up the business in the best way, there are tributes to Julia Roberts and the film within the shop itself, but it still maintains its small-town vibe.
There is something truly special about Mystic and its pizza shop, which is why a visit from a screenwriter is all it took for a major film to be set here. While you can get a taste of it from the screen, you really have to visit to experience all the magic the town has to offer — and autumn is the perfect time to revisit the film while exploring the place that inspired it.
Bangor, Maine
Is there anyone who gets through autumn without thinking about Stephen King? He's practically the king of Halloween with how much he has contributed to the holiday and the horror genre more generally. While the central locations of many of his books are fictional, they do tend to be based on real places — and many of King's inspirations are located in New England. His setting descriptions are one of the reasons the region has such a spooky vibe during this time of year.
Derry is the iconic setting of "It," but also a large number of other literary works by the author. Though not actually a real place, Derry is heavily based on Bangor, where the author's creepy mansion resides. You can visit the outer gates of this home and a number of other Stephen King landmarks, like The Barrens, the Thomas Hill Standpipe, and the gravestone that inspired Georgie's name.
The small town in Maine may appear like any other. However, just knowing that a place like Derry, surrounded by such mystique, was born here is enough to cast a dark shadow over it. Even if you aren't an "It" fan, there are mentions of Derry in other popular works like "The Tommyknockers," "Misery," and "Pet Sematary."
New Milford, Connecticut
Okay, so it's not a movie, but a "Gilmore Girls" marathon is practically a fall must, especially for the pumpkin spice caffeine fiends channeling their inner Lorelei. Let's be honest; there are plenty of New England towns that feel like "Gilmore Girls" — despite the show actually being filmed on a Hollywood set. New Milford is one of the many spots that give off Stars Hollow vibes, but it is also the town with one of the biggest inspirations that make up the Gilmores' fictional hometown.
The Stars Hollow community is always putting some kind of production on, whether it be a drama-stirring basket bidding or a climatic Firelight Festival. These events almost always take place in range of the town's central gazebo, which is very much real and can be found in, you guessed it, New Milford. The endearing structure can be seen in a large number of scenes that are set in Stars Hollow, which is why the very same gazebo placed in almost any town would easily transport fans into the show.
You'll feel just like Rory as you explore the town that surrounds the gazebo; it's just a shame that neither Luke's Diner nor Lane's family antique shop are present. Luckily, there are local alternatives you can patronize while pretending to be in an episode of "Gilmore Girls."