Sleepy Hollow, a small town in New York, is known for being peacefully quiet while terrifyingly haunted. It houses legends of the Headless Horseman and creepy school teachers, as well as celebrations of Halloween with various ghosts in attendance.
October is the perfect time to make the quick trip north to Sleepy Hollow. Only about an hour and fifteen minutes from the center of Long Island, Sleepy Hollow can be a day trip, or a family-fun weekend. Tourism to the small town skyrockets during Halloween time, so there are a ton of events and activities to do.
I visited the scenic riverside town on the first weekend of October. Colors of the leaves were already changing, neighborhood houses were decorated, and the Sleepy Hollow Cemetery was open for tours.
As I exited to Sleepy Hollow off of Route 9, signs directing me lined the streets. The town, which used to be called North Tarrytown, is not even a mile from Downtown Tarrytown, about a 15-minute walk. In an effort to reconnect the town with its famous and haunted past, the village proposed renaming their town Sleepy Hollow. A vote in favor of renaming was finally completed in 1996.
The first thing I noticed about the neighborhoods of Sleepy Hollow was the bright pumpkin-orange signs that named each street. Beekman Avenue was the center of the town, booming with businesses at the top of the road, and adorable, quaint houses towards the Hudson River. At the top of the hill, towering over the small town, stands the mansion of John D. Rockefeller.
In neighborhoods surrounding the town like Phillipse Manor and Sleepy Hollow Manor, many young families and professionals reside in architecturally beautiful homes. The decorations on houses as you drive through the neighborhoods range from traditionally spooky to modern and comical. Many of the houses used skeletons to create mini scenarios on the front lawn. One house had skeletons half buried into the ground, positioned to look like they were crawling out of graves. Another had a large skeleton, dressed in vampire fangs and a cape, standing over a group of smaller vampire-skeletons who appeared to be praising their king. My personal favorite, however, included a skeleton Taylor Swift singing on a stage, with a skeleton Travis Kelce on one knee in a graveyard with tombstones marking the names of Swift’s ex-boyfriends, a hilarious pop-culture twist of Halloween. A close runner up was Skeleton Barbie and Skeleton Ken, standing beside each other in pink and black cowboy costumes. The creativity and work that went into many of these house’s decorations are amazing, and worth the drive to see in person.
Next, I visited the Sleepy Hollow Cemetery, which is built into an extremely steep and hilly area with narrow and winding roads. The gravesites within the 90-acre cemetery look like they go on forever. The cemetery offers guided walking tours where visitors can learn the history of the grounds, its magnificent architecture and sculpture, as well as some of the legends that surround gravesites. These tours use all of their proceeds to the preservations and restoration of the grounds.
I decided to go off on my own, driving through the grounds where I could, then walking the rest. The cemetery pays homage to Washington Irving, the author of the American short story The Legend of Sleepy Hollow. The statue of a headless man reads a book, representing Irving’s story and calling him the Original Knickerbocker. (You’ll have to read the story to find out why). The guided tour will tell you Irving’s impact on American Literature and how his storytelling has lived on.
The 174-year-old cemetery hosts the final resting places of many other famous and historical figures such as Andrew Carnegie, William Rockefeller, and Walter Gurnee. However, there also lies the bodies of ordinary people who died in unordinary ways. The Murder and Mayhem lantern tour will tell you the haunting true stories of families who’ve died in some horrifying ways. Who wouldn’t want to hear true murder stories at night, in a cemetery, under the light of a small lantern?
While walking the cemetery, I came across the Headless Horseman Bridge, which is not the same as Washington Irving describes, as it is now an adaptation. Technically, this bridge is the most popular tourist destination in Sleepy Hollow that doesn’t truly exist. The bridge was said to cross the Pocantico River in the late 1700s; however, it has since rotted and has been rebuilt less than half a mile from the cemetery’s south gate.
As my day was coming to an end, I decided to eat an early dinner before heading out. Hudson Farmer and The Fish is a small restaurant with a beautiful view of the Hudson River and Tappan Zee Bridge. Their menu is designed for the season with options of pumpkin bisque, goat cheese brûlée, and sweet potato gnocchi. I sided with a more basic meal; however, I do not regret it for a second. My double stacked burger was topped with aged cheddar and a large slab of bacon. It came with a side of fries that were perfectly salted. They were short and thin, making a basket of crispy fries seem endless. I asked for a side of the sriracha aioli that comes with a few other dishes on the menu, to put on the burger and dip the fries into, making the whole meal even better.
My day in Sleepy Hollow was all about sight-seeing. But as we move closer to Halloween, the town hosts hundreds of events and activities for townies and tourists. This coming weekend, you can attend a Myths and Mysteries tour of the Octagon House built in 1860, or you can attend Hulda’s Night of storytelling in Rockefeller State Park Preserve where you can sit around a fire listening to the local legends of the town.
On Saturday, you can attend the town’s weekly farmers market, or do a self-guided tour of the Lyndhurst Mansion, only open the two weekends before Halloween. The Great Jack O’Lantern Blaze is known to be absolutely breathtaking for both kids and adults. Next Saturday, October 28, the town will get together for the Sleepy Hollow Halloween 10K, followed by live music, beer tastings, and a one-mile Fun Run. The Tarrytown Halloween parade will be hosted the same weekend followed by a block party that townies say not to miss.
Sleepy Hollow is absolutely worth the trip any weekend of October. There is history and story-telling galore and always something happening around town. When visiting, be respectful of the cemetery, and the houses of people who live their everyday lives in the town, and for your own sake, I hope you do not see the Headless Horsemen during your visit!
