In These Real-Life Halloweentowns, October Is Both Scary and Sweet

Halloween was always more exciting in Sleepy Hollow. Even before my family moved there when I was 11, my mom took me trick-or-treating in my grandmother’s neighborhood under the shadow of the Old Dutch Church, the Sleepy Hollow Cemetery, and the beloved tunnel of sycamore trees that leads the way into town from the north. It always felt extra spooky, like something intangible hung in the air. The writer Washington Irving, who is buried in the cemetery, clearly noticed this as well, though he sadly never experienced the joy of collecting fun-size Snickers while dressed as the pink Power Ranger when he wrote his 1820 short story The Legend of Sleepy Hollow. In it, he says, “The place still continues under the sway of some witching power that holds a spell over the minds of the good people, causing them to walk in a continual reverie. They are given to all kinds of marvelous beliefs, are subject to trances and visions, and frequently see strange sights, and hear music and voices in the air.”

In his famous tale of the Headless Horseman, Irving also called Sleepy Hollow “one of the quietest places in the whole world.” Nowadays, come fall, there couldn’t be a less appropriate description of this village just 30 miles north of Manhattan on the Hudson River. On any given weekend in October, tourists line up to snap pictures with the “Welcome to Historic Sleepy Hollow” sign near my old high school. If you’d asked me when I lived there, I would’ve said it was a purely utilitarian marker separating Sleepy Hollow from Tarrytown, its adjacent sister village (with which it shares a zip code, school district, and plenty of history). But now, these small towns of roughly 11,000 residents each have taken on a new life. In 2024, the villages welcomed between 100,000 and 150,000 visitors during the month of October alone.

“It’s shocking,” says Sara Swan, owner of The Swan’s House, a vintage furniture boutique in Tarrytown famous for its “Miami Vice meets Mad Men” Art Deco–era pieces. “We’ll see tourists [even in September] dressed up as witches.” When she moved to town in 2017, she says, “it was not what it’s become.”

Photo-op fever isn’t unique to Sleepy Hollow—remember earlier this year when the owners of Carrie Bradshaw’s brownstone had to put up a gate to keep the throngs away?—and neither is an amped-up fervor for Halloween. According to the National Retail Federation’s annual survey, consumer spending surrounding Halloween is projected to reach a record $13.1 billion in 2025, and ever since the term “spooky season” took over the internet, we’ve all seen it creep onto our feeds earlier and earlier each year.

My hometown isn’t the only place where Halloween tourism is booming at frightening levels. The 14,000-person town of St. Helens, Oregon, situated on the banks of the Columbia River, could’ve had just 15 minutes of fame when it served as the main filming location for the cult-favorite 1998 Disney Channel Original Movie Halloweentown. But around 2015, when an annual local gathering paying homage to the film—complete with a giant pumpkin in the town square—started growing, the town capitalized on the nostalgia. Last fall, St. Helens’s Spirit of Halloweentown event raked in $1.2 million in total gross revenue and brought 67,580 people to town over five weekends.

“I feel like it increases every year,” says Kimberly Adams, general manager at the Klondike Tavern in St. Helens. “It’s crazy to see [us] on some random person’s TikTok about Halloweentown. To us, it’s just home.”

In Salem, Massachusetts, arguably the witchcraft capital of the country, Halloween has been an affair to remember since even before the first Haunted Happenings event there in 1982. But in October 2024, the city saw 1.04 million visitors partaking in the numerous museums, occult shops, and other attractions—87,351 visitors (almost double the population) filled the sidewalks on Halloween day alone.

“[Tourism in Salem] just really exploded after the quarantine part of COVID. It was always growing, but it really reached a critical mass in 2021 or 2022,” says Erica Feldmann, a practicing witch and the owner of HausWitch in Salem, a store offering aura photos and spell kits that promise to improve your home’s energy. During October, customers often wait an hour just to get in the door.

Feeding the beast

No trespassing signs are posted outside of this Salem home, which appears in the 1993 film Hocus Pocus. Photo: Katye Martens Brier / The Washington Post / Getty Images

Each town may have lit its own tourism flame (when the General Motors plant closed in what was once known as North Tarrytown in 1996, residents voted to change the name to Sleepy Hollow, hoping to lean into the historic identity and stimulate the economy), but the lighter fluid of social media has meant that crowds can balloon unexpectedly, sometimes beyond what existing infrastructure can handle or what organizers are prepared for.

When Dani, who moved to Sleepy Hollow four and a half years ago after being charmed by its downtown feel and lack of cookie-cutter, suburban strip malls and chains, attempted to attend the town’s annual October street fair last year, she turned around and left the event immediately upon arrival. “It was almost an unsafe level of crowd. It was completely overwhelming. We literally couldn’t even walk through,” she says.

After that event, the Village took to Instagram to address complaints and promise that discussions about “how to improve traffic routing, safety and event sizing” were underway. This year, that same street fair was held in September instead of October, but still drew between 15,000 and 20,000 visitors and garnered some Reddit griping about crowds.

“The Village does not promote a lot, because the influencers already promote the events,” says Diana Loja, Village of Sleepy Hollow community liaison. Instead, the Village focuses on safety, mitigating the parking and traffic issues, and spreading the word that visitors should take the train to town.

Crowds at the Tarrytown Halloween Parade in 2023. Photo: Margaret Fox Photography

“That first year when there was just this huge influx of people, all the restaurants were packed and none of us were ready for it,” says Adams of St. Helens’s first surge. “We all sold out of food, and we had lines two hours long waiting for dinner. The businesses were just like, ‘How do we handle this?’ It turned everything into chaos.” Over the years, she’s learned that, come October, menu items need to be “speed-friendly.”

Halloween hibernation

Even after abandoning ship at the street fair, Dani is happy with her life on the Hudson River. But for her and others, the changing leaves signal an adjustment to daily routines. For example: “I don’t want to go get a prescription in October,” she says.

It’s a specific example, but a common one: The line at CVS in Salem also kept HausWitch owner Feldmann from grabbing prescriptions during spooky season when she lived downtown—or really doing anything that required moving her car at all. “You just feel trapped,” she says. “You’re not eating at restaurants, you’re not going to get coffee at coffee places. It’s just for the tourists.” Alee DiGregorio, a Tarrytown mom, echoes this sentiment: “I’ve had to pay thousands of dollars to Instacart.”

Restaurant workers like Adams at St. Helens’s Klondike Tavern miss their regulars, who tend to disappear and reemerge come November. “Locals become strangers in October,” says Mikey Segarra, a lifelong Sleepy Hollow resident who, last year, was told to “get in line” while trying to enter his own home amid the festivities. To be fair, the tourists aren’t all bad. In 2017, he met a firefighter from Louisiana and his wife, in town for their annual three-week RV trip to the area, and since then, they reconnect and grab a beer each year.

Deyanira Cabreja, a nail artist who works by appointment only in a small Tarrytown office building, says last year was such a “nightmare” with all of her clients being late to their appointments due to traffic, that she had to close her salon on Saturdays. “It is tough for me and it’s annoying sometimes, but all you can do is just try to have patience,” she says, noting that she, too, still loves her hometown. “I’m a proud Horseman.”

Even the Sleepy Hollow High School class of 1970 opted to forego their reunion on traditional fall homecoming weekend and schedule it for August instead. “People couldn’t get hotels, and there’s just too much going on,” says one of the organizers, a lifelong Sleepy Hollow resident.

Getting in the spirit

Though October may be evolving into a time of hibernation for some, it’s not like these townspeople are a bunch of Halloween Scrooges. It was St. Helens locals, after all, who helped ramp up interest in the Spirit of Halloweentown event, and a local mechanical artist, Byron Ohler, is responsible for creating the town square’s giant pumpkin that mimics the one in the film. In a new documentary about St. Helens (available to rent on Amazon, Apple TV, and YouTube on October 24), his wife Colleen—the pair are known locally as the king and queen of Halloweentown—is shown preparing small rubber duckies to hand out to children during the event. Later, she reveals that it had been a tough year at the time of filming, during which she lost her mother and her job. “Honestly I’m so grateful for Halloweentown this year,” she said. “It has given me a lot to be able to concentrate on and not think about myself.”

Dani Spencer, a Halloween enthusiast known online as Dani October, can relate. After being a longtime visitor to both Sleepy Hollow and Salem, she moved to the former in 2018—and then to the latter in 2023. She enjoyed mingling with tourists at the Old Dutch Church; now she does the same at Charter Street Cemetery in Salem, and she hopes to eventually start her own walking tours. Fall is when she shares her love of Halloween—and even moreso, history—with others, while she has the rest of the year to indulge in it herself.

“A lot of us who love Halloween, we were just strange and different kids. Growing up, my fondest memories were when the fall came around and it felt like the rest of the world caught up to me,” she says. “I wasn’t looked at as any different [during that time], because everyone else wanted to be strange or unusual or dark.”

Keeping the jack-o’-lantern lights on

“Back in 2009, I bartended on Halloween night, and there was nobody in the restaurant,” says Julia McCue, owner of Horsefeathers in Tarrytown. Now, half of her business’s yearly revenue is made in the final quarter of the year thanks to Halloween tourism. Courtesy of Horsefeathers

Though miles apart and each with a different Halloween origin story, Sleepy Hollow, St. Helens, and Salem have plenty in common: Locals battle over parking and traffic in comments sections and village halls. They share disbelief when they stumble upon a carefully edited influencer video proclaiming all the best spots to visit in their town. There’s a lot of pride, love, and community–right alongside differing opinions about how “the whole Halloween thing” should be handled. Residents are watching their towns evolve, for better or worse, before their very eyes. And many have also seized business opportunities which wouldn’t have existed for them without Halloween.

Those who have been able to capitalize on the influx agree—the autumnal boost makes it possible for them to survive and thrive. ”I’m really grateful for the crowds,” says Feldmann of HausWitch. “This time of year is what allows me to run my business in the way that I like to run it, which is anti-capitalist in spirit and about supporting my employees above all else.”

“October, November, and December are the three months that keep our business alive, and I’m sure that goes for all of the shops in town,” says Swan. “We have three times as much business in those months.” It may not be obvious to design lovers who follow The Swan’s House on Instagram for the Milo Baughman chairs and ceramic clamshell lamps, but Sleepy Hollow–adjacent merch—both new and vintage—is a consistent bestseller for the store. All year long, Swan keeps her eyes peeled for anything with horses or pumpkins on it when she scours estate sales.

“Either you lean into it and you enjoy it, or you hate it,” says Julia McCue, owner of the restaurant Horsefeathers in Tarrytown—and she’s long been an advocate for leaning in. With residual hardships from COVID and rising inflation threatening to shutter small businesses like hers, she sees the tourism boost as a way to keep the beloved restaurants and stores in town alive. “Otherwise the only people who really can afford to come in and open a business here are large chains and corporations.” And really, that’s not what the thousands of visitors who enjoy these towns fell in love with.

For Holcombe Waller, who purchased the Klondike Tavern in St. Helens in 2021, there’s an opportunity to expand even beyond the already packed October weekends. The building that houses his restaurant was once a hotel, and as he puts it, “Everybody knows that the Klondike’s haunted.” That lore, he figures, is sure to be good for business when he eventually renovates and reopens the space as a boutique hotel right in the heart of Halloweentown. “I’ve never heard a haunting story about the Best Western, you know what I mean?”