Located 25 miles north of New York City on the eastern shore of the Hudson River, the lovely village of Sleepy Hollow offers visitors a small town feel, an abundance of history, striking architecture and riverside views. This native New Yorker, however, had never been there. And it was certainly about time to find out what enchants visitors from around the world. So this past weekend, my husband and I decided to enjoy an afternoon getaway to Sleepy Hollow, New York. And we were not disappointed!
Sleepy Hollow’s popularity, especially around Halloween, has soared.
It’s no wonder. Movies, TV shows and even cartoons have all popularized Washington Irving’s short story, “The Legend of Sleepy Hollow,” and its infamous character, the Headless Horseman. And this town has embraced this legend.
Whether passing by its local fire department or one of its residences, one can see how Irving’s short story is truly embedded in the very soul of this town. Take a look at these decorations!
In front of Sleepy Hollow Firehouse 
A decoration in front of a residence
Of course, this infamous story is a major draw for most visitors. But this town is more than just a short story. Let’s first take a brief look at its…
HISTORY
It is believed that this village’s first European settlers were Dutch. However, back In 1609, the two square miles that make up Sleepy Hollow actually belonged to the Weckquaesgeck Indians. For awhile, New Netherlands and this tribe lived peacefully together.
Unfortunately, by 1643, the Dutch were at war with the Weckquaesgecks and several other tribes of the region. In 1655, Adriaen Van der Donck, a Dutch colonist, published a work which referred to the Pocantico River as Slapershaven or, translated as Sleepers’ Haven. Sleepy Hollow is most likely an Anglicized version of this name and actually referred to the valley of the Pocantico River.
Today, it serves as the name of the incorporated village.
Fast forward to the 20th century. In 1996, General Motors, a major employer in the area, closed its plant, leaving over 4000 jobs behind. But this town’s resilient locals decided to take action and rebrand itself. How? By renaming North Tarrytown as “Sleepy Hollow.” And the rest is, of course, tourist history.
So now that we have a bit of history under our belt, let’s start exploring.
THINGS TO DO
Sleepy Hollow is a walkable village, albeit a bit hilly in spots.
We started along Main Street passing many shops, restaurants, parks and schools. It truly feels like a close knit community.
Our first stop was Philipsburg Manor, a restored 18th century trading and milling living-history museum that focuses on the lives of enslaved Africans. Unfortunately, it is closed until further notice due to Covid. But no worries. Other notable sites are just nearby. Right across the street, is the famous…
Headless Horseman Statue.
According to Gothic history, the headless horseman is a supernatural entity which represents a past that never dies, but always haunts the living.
In Irving’s story, the headless horseman is believed to be a Hessian soldier, decapitated during the war, who seeks revenge—and a head—which he thinks was unfairly taken from him. To this day, he supposedly continues to haunt the town in search of his head.
Heading up the road (no pun intended!), you will arrive at the entrance of two famous sites …
Dutch Reformed Church and Cemetery
Listed on the National Register of Historic Places, the Old Dutch Church of Sleepy Hollow is a beautiful 17th century stone church. Visitors are allowed to enter and take a look inside the small church. Masks are required.
A View through the church window of the Church Burial Ground. 
Its windows provide views of the church’s 2.5-acre burying ground which is, of course, the purported haunt of the headless horseman. It is also the resting place of local citizens who likely inspired Irving’s characters of Katrina Van Tassel, Brom Bones, and more.
Next stop is …
Sleepy Hollow Cemetery…
which surrounds the Old Dutch Church Burial Ground. Whether you are a history buff, love sculpture, or enjoy pretty scenery, a visit to its 90-acre grounds is must.
Andrew Carnegie’s Grave 
In front of Washington Irving’s grave 
William Rockefeller’s grave
Open daily from about 8 a.m. to 4 p.m., visitors can walk the many paths and explore the graves of the famous and not so famous. Washington Irving is buried here on a hill overlooking the older cemetery. It is also the resting place of many famous people including William Avery Rockefeller Jr., Andrew Carnegie and Harry and Leona Helmsley.
Please keep in mind, however, that this cemetery is still used for burials. Be respectful.
Located about .3 miles from the cemetery’s south gate is the…
Headless Horseman Bridge
In local folklore surrounding the Headless Horseman, it is believed his crossing of this bridge carries him from the land of the dead to that of the living – and back again. In Irving’s story, the main character, Ichabod Crane, flees from the Horseman. He rides towards the bridge in the hope of crossing a magic line of safety, a point where the Horseman’s powers dissolve.
In real life, this cemetery bridge is used daily by funerals and mourners visiting graves. Be respectful of those living and those who are deceased.
After getting our fill on all things related to “The Legend of Sleepy Hollow,” we were ready for a change of course. A relaxing riverside stroll was in order so we headed down towards the…
Scenic Hudson River Walk Park
On our way to the river, we walked through some amazing neighborhoods that showed the beauty and diversity of the area.
Hudson River Walk Park is quite beautiful, offering stunning views of the Hudson River and Tappan Zee bridge. A good part of this expansive area is currently under construction. Ultimately, when completed, it will provide its residents access to the Hudson that has been inaccessible for more than a century.
Sleepy Hollow Lighthouse 
The Hudson 
Tappan Zee Brigge
Walkways will connect to new and existing trails and parklands in a gorgeous outdoor recreation space. I can’t wait to come back and see when it’s finished.
Towards the end of the walk, you will arrive at the Sleepy Hollow Lighthouse, erected in the 1880s. In 1979 it was listed on the National Register of Historic Places. Unfortunately, you couldn’t go inside by we still got a picture!
(Important tip: Sunnyside, Washington Irving’s home, which is a bit outside of the main area of town, is the first stop for many tourists when visiting the area. If this is top on your list of things to do, book your tickets online asap. Unfortunately, since our getaway was spur of the moment, we couldn’t get tickets. But no worries. As you can see, there is a lot to experience in this lovely Hudson Valley gem.)
After a full afternoon of exploring, our tummies were grumbling. It was dinner time! As always, I did a bit of research before we left home and put together a short list of possible eateries. Our choice was Leftisit Greek, located on Main Street, offering a traditional Greek menu. Yummy!
After filling our bellies, we topped off our day with a stop in a local shop to pick up a few souvenirs. What a beautiful day!
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Sleepy Hollow is a perfect Hudson Valley getaway for a day or even a weekend. The history and beauty of the area offers much for visitors. My husband and I hope to return soon and explore more of the area. Top on our list includes: Sunnyside (Irving’s home), Rockefeller Park State Preserve (for hiking) and Kykuit, the Rockefeller estate.