Wendy's trip log: Sleepy Hollow NY Home of the Headless Horsemen.

Sleepy Hollow, NY

10/5/23

I am sorry that I rushed through the last post. It was actually a sad trip, and I had already expressed all the good things in the 2022 Vermont trip. My mind was elsewhere on this trip and although I tried to keep a happy face while in Vermont, I have dealing with things back at home. Promise this trip will be a ton more exciting, and it totally is.

When Nikki said she wanted to take a trip to Sleepy Hollow this fall, I was all in. I love this kind of stuff and I had been wanting to go see the area that inspired the Legend of Sleepy Hollow for some time. This was a perfect time to go, Halloween is coming and where better to enjoy the season but in the area of where the HEADLESS HORSEMEN rides.

It was about a 31/2 hour drive from our home in central NY. The trip included this traveling trio. Me, Nikki and Tammi. The plan was to do everything Sleepy Hollow had to offer and drive home. It was a feet, but we were going to make it happen. Those three and 1/2 hours flew by as we chit chatted the whole time. It was soon and we were in this historical little hamlet.

Sleepy Hollow was originally land inhabited by the Weckquaesgeck Indians. (I've never heard of this tribe.) In the 1600's as the Dutch began to settle in NY and establish farms in the area. A wealthy Dutch colonist named Fredrick Philipse acquired the property which includes most of todays Sleepy Hollow. It was known in Dutch as Slapershaven which translates to Sleepers Haven, and inlet of Terrytown.

In the 19th century Sleepy Hollow was the home of the company Stanley Steamer and General Motors also had a large company located here.

There really is no guide on how to explore Sleepy Hollow, so we were just kind of going with the flow. We decided that we would go the the Sleepy Hollow cemetery first. The old church that sits on the edge of the cemetery is The Old Dutch Church and it is the second oldest church in NY and 15th oldest building in the state. That makes it pretty old. The original building was built in 1685. A fire destroyed some of the structure in1837 and it was restored to its current presentation. The building was designated a National Historic Landmark in the 1960's.

(the church was not open, but I did try to get a picture through the window)

The village of Sleepy Hollow would possibly be like any of the other small towns dotted across the lower east part of NY except that there was a popular writer named Washington Irving who made the village famous with his writing of the Legend of Sleepy Hollow. Irving lived in the nearby Terrytown on his estate named Sunnyside. He is also buried here in this cemetery. The story of skiddish teacher Ichabod Crane was set here.

We decided to take a walk in the cemetery in search of Washington's grave site. If you are interested in old cemeteries this one has lots of highlighted stops. There are two War Monuments; The Civil War and The Revolutionary War Monuments, several mausoleums, the grave of Andrew Carnegie (which we did search for but couldn't find), Washington Irving's grave site, (which we did find) and the Headless horseman bridge. (Other notable gave sites include Elizabeth Arden, Leona Helmsley, William Rockefeller, and Walter Chrysler).

There are definitely some old stones here. I wasn't fearful during the day, but I am sure that this place can be scary at night.

After some exploring of the cemetery, we headed to the famous bridge where Ichabod rides to escape the Headless Horsemen. (this is not the original bridge, but it was neat to imagine.)

Here I will retell in summary the tale of The Legend of Sleepy Hollow.

The short story was written in 1820 and set in the 1790's in the quiet town of Sleepy Hollow. School Master Ichabod Crane has been enchanted by the beautiful Katrina Van Tassel. Unfortunately for Ichabod, there is another who finds Miss Katrina just as enchanting. Abraham (Brom Bones) Van Brunt. Brom, unable to get Ichabod to fight for Katrina, sets about to ruin Ichabod through jokes and harassment. It is at a party held at the Van Tassels estate where Brom tells party guests the tale of the Headless Horsemen. Superstitious Ichabod, believes the tale of the headless ghost decapitated by a cannonball during the Revolutionary War.

Brom continues the tale reporting that the ghost, buried in the local churchyard rises from the grave each night in search of his missing head. In the story Ichabod's fear increases upon every word. Brom concludes the story by noting that the only way to escape this Headless horseman is to cross the wooden bridge. Katrina denies Ichabod, and he leaves the party both heartbroken and scared. In order to get home, he borrows a plow horse named gunpowder. Upon his ride he encounters a dark cloaked rider. Ichabod believes this to be the headless horsemen and begins to ride for his life towards the bridge. This headless rider in pursuit, sends his head towards Ichabod knocking him from Gunpowder. Ichabod was never seen again, the only thing left of him was his hat, which was found next to a smashed pumpkin.

Apparently he never made it to the bridge. The story leaves the reader with questions. Was there a real Headless Horsemen? Or perhaps it was just Brom hoping to scare Ichabod out of town? He did end up marrying Katrina in the end. One may never know.

We headed towards the main street of town, stopping to see this sculpture.

We then went to the downtown area and walked the streets in search of lunch. We had pizza at Beekman's Ale house.

There were some creepy things on the street.

The pizza was so yummy.

We did a little shopping and exploring of the town. It is very cute. We could easily spent several day exploring the area, but we had to get back home. We did try and visit Sunnyside, but it was closed by the time we would have gotten there.

Fortunately we were allowed into the grounds of Lyndhurst. The cost to visit this place is $27-per person but the guy at the gate made us promise to just look. How nice of him.

We did more then just look, but I am pretty sure he knew that. This place is beautiful. Designed in the Gothic Revival style in 1838 by Alexander Jackson Davis. Three families resided within the home.

Mayor of NYC William Paulding and his family resided here and it was known as Paulding Manor. His son Philip made the place his home until the 1950's.

George Merritt purchased the property and worked with Davis to expand the property. (1864-1865) With this expansion the property became Americas most impressive Gothic Revival homes. Merritt died shortly after the expansion, and his wife and children were left to run the expansive property. She decided to sell in 1880. It was then purchased by railroad tycoon Jay Gould. He and his family enjoyed the property even after he and his wives death. His daughter Helen maintained the property and she and her family used it as a summer home. After Helens death the youngest daughter Anna took ownership of the property. Upon Anna's death the property was left to the National Trust for Historic Preservation. It opened as a museum in 1965. So many of these amazing mansions along the Hudson river were barley lived in, often used as summer homes or vacation retreats. I so wish I had one, even a little small one would be ok, just to live in full time.

We walked the grounds and visited the welcome center and store. Apparently there are haunted events that take place during the season so the yard was decorated for the festivities. There is also a nightly pumpkin event that is held during the Halloween season, among other themed events throughout the area. I would recommend that you look into the many tours and events that take place during the season.