When a Sleepy Town Goes Viral, Homeowners Pay the Price 

For two centuries, the legend of “Sleepy Hollow” and the Headless Horseman has delighted fans of all ages, especially at Halloween. 

Those who live in the tiny, namesake hamlet in downstate New York have enjoyed the notoriety of being home to the tale’s author, Washington Irving, leaning into the season every October with events like a Halloween parade, street fair, and a block party for residents.

But what was once a local celebration held with sister city Tarrytown in their quiet, shared neighborhood has turned into a massive undertaking, after social media influencers blew into town four years ago. 

During the travel boom that followed the COVID pandemic, many travel bloggers made the trek to Sleepy Hollow to have an “authentic” American Halloween experience. Reaching the masses on Instagram and TikTok, they encouraged visitors to make the drive an hour outside of Manhattan to soak in some spooky vibes. 

But the real scare is what now awaits homeowners in the area every season, as their lives are upended from mid-September right up to Halloween night, as their peaceful community turns into an overrun nightmare. 

The truth about Sleepy Hollow and Tarrytown at Halloween 

It happens all over the country: New Orleans has Mardi Gras. Manhattan is impossible between Christmas and New Year's. And these days, Nantucket, MA, is so overrun by tourists every summer, workers are sleeping in their cars from May to September due to a lack of housing.

Now, the pair of neighboring villages in New York's Westchester County are feeling their own growing pains of being a tourist destination once a year. Home to roughly 20,000 residents between them, the two towns are currently coveted seller's markets, with buyers gobbling up properties quickly after they hit the market to live with accessibility to Manhattan and soak in the natural surroundings. 

In September 2025, the median listing home price in Sleepy Hollow was $1.7 million, trending up 38.1% year over year, while it stood at $824,500 in Tarrytown during the same time, according to the most recent Realtor.com® data. 

While an idyllic place to live, the small town’s charm is matched by its small town size, meaning it’s far from equipped to be a tourist destination, even for only a few weeks. 

And the lack of infrastructure for visitors has made it difficult for residents to enjoy their towns during the Halloween season. 

Lucia Ballas-Traynor has been involved with the local Chamber of Commerce for five years, the last two years in the executive director position. She’s seen firsthand what’s been happening in her town. 

“Prior to COVID, the annual street fair would get 5 to 6,000 people attending,” she told Realtor.com. “In the past couple years, it’s increased to 20-25,000.”

An astronomical jump in attendance, especially when you consider the street fair is only three blocks long. And locals are feeling the crunch. 

“Everyone around here knows, halfway through September, buckle up because it's starting,” one lifelong resident explained to Realtor.com. As a local teacher, they’ve seen how the area has changed from witnessing a handful of tourists stopping by to throngs of visitors “descending upon the village” because of social media. 

“I wanna say it was our Halloween parade four years ago, where we had more tourists come to town for our parade than we have residents in the village,” they added. “It's been a lot to manage.“

Halloween horrors and how the town’s responding  

Along with the aforementioned parade and street fair, Sleepy Hollow has met the demand of visitors by adding cemetery tours, artisan shopping, and the Great Jack O’Lantern Blaze, which is technically in Croton a few towns over.

But when it comes to the main events in town, and hoards of out-of-towners start flooding in, the town’s main responsibility—and perhaps the biggest complaint from residents—is clearing the “main artery” of the community, as Ballas-Traynor calls it. 

Route 9 is the only way in or out of the area; it’s also the location of one of the town’s main attractions—a 18-foot-tall sculpture of the Headless Horseman chasing Ichabod Crane, created by local artist Linda Perlmutte. So, as you might imagine, especially on weekends, traffic control becomes a main priority.

“There’s so much traffic,” Ballas-Traynor recalls, thinking back to that first street fair after the pandemic. “There’s just no parking anywhere.”

And it’s been the case ever since. So much so that the villages hired a "specialist" to help with traffic flow, and the Chamber of Commerce started an active campaign to encourage visitors to take the train if they’re coming in for the day. The initiatives have helped, but only so much. 

“I just want to go down to the restaurant,” the resident told Realtor.com. “I just want to walk down the street. I want to drive to see my parents on the weekends and I can't. It takes too long to go see them.” 

On Reddit, another local said, “This happens every year. All of October is a madhouse and it takes forever to go anywhere because of all of the pedestrians with no regard for their safety or others blindly walking in the street without looking and stopping to take pictures.

'We have been here for four years and have never been able to enjoy any of the fall festivities because tickets are always gone.” 

Does it help the town to go viral?

With all of this said, one might think that the upside to the influx of tourists equals an influx of money coming into the town. 

While that is definitely the case for the local restaurants and shops, for the town itself, it actually costs more money. 

“It’s an expense,” Ballas-Traynor explains. “Tourism doesn’t generate revenue [for the town]. It means you have to hire and increase security, sanitation folks, police, etc. There’s a lot of other costs associated with it. Maybe you haven’t even thought of this, but even people using bathrooms in some of the businesses that aren’t used to having all these visitors can lead to extra plumbing costs. Or the cemetery having to rent porta potties—and not just pay for the porta potties, but also for their servicing.”

And the residents are paying their fair share as well.

“Last year, on Halloween itself, we had so many out-of-towners, people coming from other towns to trick or treat in the town that by 5:30, almost everyone had run out of candy,” the local teacher shared. “And candy is expensive!”

And yet, Ballas-Traynor admits that it might all be worth it, maybe not for the residents but for the business owners. 

“It's a month or two out of the year,” she adds. “And it’s a lifeline to these businesses. It's still manageable enough. It's not like Salem or like other places where it’s completely out of hand. I don't think we've reached that point.”

It certainly hasn’t deterred potential new residents from clamoring to move in either. 

“A lot of people that come to visit, they’re like, ‘oh my God I would love to live here.’ And not necessarily because of Halloween, but because of nature and because of accessibility for the city,” Ballas-Traynor says.

But in a commitment to the residents, Ballas-Traynor shared that truly local events for this Halloween, like trunk or treats, were kept off social media pages to preserve the experiences for locals. One resident had another suggestion.

“Can we get a stipend from the town for candy?!”