I Lived Near the Spookiest Town in the U.S. — Here's What It Was Actually Like
I love Halloween. I loved it when I was a kid, loved it as a parent of young kids, and I love it now. These days my kids are long out of college, and my wife and I have long since downsized and moved to a 55-plus community in Pennsylvania. We won’t have any children knocking on our door on Halloween — no kids dressed as pumpkins, witches, or ghouls, asking for candy bars and tricks or treats. But before my wife and I moved out here, we lived just a stone’s throw from one of the most over-the-top Halloween towns in the world: Sleepy Hollow, otherwise known as Tarrytown, in Hudson Valley, New York.
I haven’t been back in a couple of years, but the times that we celebrated Halloween in Sleepy Hollow were always worth the trek. And it is a trek. Every year, from roughly late September to a day or so after Halloween, Sleepy Hollow attracts tens of thousands of tourists — an estimated 80,000 to 100,000 people throughout October — who soak up the atmosphere, celebrate All Hallows Eve, dress up in elaborate costumes, visit haunted houses, and so much more. (Tarrytown/Sleepy Hollow usually boasts a population of only 11,000 people — meaning that the town swells almost eight times its size for a month of the year.)
But why the onslaught of tourists, really? It started hundreds of years ago. Local resident Washington Irving published The Legend of Sleepy Hollow in 1820. That classic horror short story — featured in a collection titled The Sketch Book of Geoffrey Crayon, Gent — introduced readers to Ichabod Crane and the Headless Horseman. And it transformed the harmless pumpkin into something far beyond — more sinister than a mere vegetable.
A quick look at the Sleepy Hollow website reveals why (and makes me feel exceedingly jealous of all the fun and games we’ll miss out on). This year, the town will put on a long list of activities in and around the village to enjoy/fear: Spirits of Sleepy Hollow Country, Octagon House Tour with Reading of The Raven, Rock N Roll House of Horrors, the Vampire Circus, Dracula and the Theater of Doom, Ghost Tours of Tarrytown Music Hall, the Run for Your Life Halloween 10K, the Great Jack O’Lantern Blaze (with its 7,000 illuminated pumpkins), and, of course, the annual Tarrytown Halloween Parade. Fittingly, the parade kicks off at Patriots Park, once the home to Wiley’s Swamp, depicted in The Legend of Sleepy Hollow as the spot where Ichabod Crane initially sees the Headless Horseman.
I’ve been there a handful of times, and while I love it, I know that my experience as a visitor is far different than what the locals probably feel about it. It’s like living on Cape Cod and dealing with summer traffic, or in Midtown Manhattan during the St. Patrick’s parade. Sure, thousands upon thousands of people (my family included) visit Sleepy Hollow for ghostly delights, but where are the locals during all that?
They’re at home.
“I haven’t taken advantage of most of Sleepy Hollow’s touristy spots since I was a kid on school trips,” says Tom Weaver, a journalist, film and TV historian, and lifelong local. “I have no idea what they’re like today. Sleepy Hollow residents like me hunker down in their homes for the days leading up to Halloween. The town is packed with tourists. Our streets, half-empty of traffic 360 days a year, are like Times Square; and the sidewalks the same way with people. As a resident, you have no desire to go out!”
Lucia Ballas-Traynor is Executive Director of the Sleepy Hollow/Tarrytown Chamber of Commerce. It’s her job to advocate for the village and its businesses, and to work with the village government. She’s also a realist. Locals appreciate the Legend of Sleepy Hollow connection, take pride in it, and know it’s good for certain businesses, she says, but occasionally grow weary of the droves of tourists.
“Many of the locals stay away, honestly,” Ballas-Traynor says. “I live in Tarrytown, and it’s walking distance to town. But [it’s] a residential area for the Halloween parade [and] we have cars parking all the way up to where I live — on side streets, everywhere. The day of the Halloween parade, it took me an hour to go about a mile and a half. Basically nothing else can happen [that day].”
Ballas-Traynor calls the history “an important part of this place,” but stresses that it’s not why she and her family, which includes husband, Michael, and their two children, chose to live there.
“I moved because of the proximity to the river,” she says. “No matter where you go in Sleepy Hollow and the village, you always have the majestic Hudson River behind you. I moved here because of nature trails. You have the Rockefeller State Preserve. It’s 1,700 acres of beautiful trails. Also, the culture here versus where I come from, people are down-to-earth and friendly. It’s a very quaint town, Tarrytown.”
As for the locals who steer clear of Sleepy Hollow the week of Halloween, it’s much like people who live in Manhattan and have never been to the Statue of Liberty or the M&M store in Times Square.
“That’s exactly it!” Ballas-Traynor says.
Suffice it to say that I was not one of those people who avoided tourist destinations, not when I lived close to Sleepy Hollow and not about Halloween at all. One thing I miss the most about my old homes are the Halloween memories: I grew up on Long Island, and my block boasted 26 houses (and the streets surrounding us had just as many). When we lived in Midtown Manhattan, my kids went door to door on every floor. And later, just a stone’s throw from Sleepy Hollow, we’d drive out to the best trick-or-treating spots, where my kids would get candy apples, bags of popcorn, and full-sized candy bars.
As I stare down the reality that I may have a Halloween without trick-or-treaters, I’m considering heading back to Sleepy Hollow for October 31 — or at least sometime this month. I want to keep the kid in me alive. And, if nothing else, I’ve already got my eye on a haunted house walking tour through New Hope to keep the spooky spirit (and the kid in me) satisfied.
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