Spooky Halloween Tradition: The Headless Horseman

Sleepy Hollow Cemetery

On the banks of the Hudson River, is a quaint little town called Sleepy Hollow, formerly known as North Tarrytown. Housed here is the Sleepy Hollow Cemetery, one of the most historic cemeteries in New York. Maybe even in the Northeast. The Sleepy Hollow Cemetery is a large property with rolling hills with a rushing Pocantico River racing through.

This is the final resting place of New York royalty such as Elizabeth Arden, Brooke Astor, Andrew Carnegie, Walter P. Chrysler, and the Hemsley’s. Leona Hemsley is famous for leaving millions of dollars to her pets when she passed away. While the rich and famous did not spare a penny on their lavish tombs – The Hemsleys have an impressive massive tomb with 4 stunning stained glass windows of the Manhattan skyline, our reason for visiting is the much more humble graves that surround the original Old Dutch Church.

Every year, since Lily was about 7, we have made it our annual tradition to go to the Sleepy Hollow Cemetery for our spooky Halloween fix. I think it was in 1st grade that Lily was reading some of Washington Irving’s books and when we realized the wealth of secret – not so secret-history that lived… or had died... just a few miles away, we had to visit.

Washing Irving, author of some of our favorite books – Rip Van Winkle and The Legend of Sleepy Hollow – lived in Sleepy Hollow. This town was originally known as North Tarrytown and was only recently changed to Sleepy Hollow as an ode to the famous story.

But that’s not all. Did you know that Washington Irving himself is buried at the Sleepy Hollow Cemetary? And it gets even better… He found the names of his characters from the graves that surrounded the Old Dutch Church. Ichabod Crane… found his grave. Katherine… she’s there too.

The story of Rip Van Winkle was inspired by the Town of Irvington with its steep hill down to the train station and Hudson River.

The story goes that the Headless Horseman to this day roams the grounds of Sleepy Hollow Cemetery looking for his … head. There is also the legendary bridge that he can’t cross. (not the original).

Lily loves this tradition and while we have taken Thomas the past few years, he doesn’t quite remember.

This year was just like any, gorgeous fall weekend, stunning colorful firey leaves all over the grounds. We parked right in the cemetery. Insider tip: enter through the north entrance and park in the cemetery so you avoid the crowds through the south entrance. It’s a beautiful walk through the cemetery grounds with draping trees, stairs, hills and stunning views. We like reading the descriptions on the graves. Some of the graves were just stunning and ornate and others much more simple. Nevertheless, it’s beautiful.

We made our way down the hill to the Old Dutch Church to find Ichabod and Katherine and walk through the oldest graves on the property. On the way, we stopped by Washington Irving’s grave and collected leaves for our collection.

While I was nose deep in reading tombstones, Matt gave me a nudge… and there he was!!! THE HEADLESS HORSEMAN!

Of course, we had hyped this whole thing up with the kids. And talked to them about how the Headless Horseman roams the cemetery and that he is always looking for new souls to take and heads to attach onto his headless body and if any of us ever see him… the emergency plan is to RUN to the nearest body of water – the Pocantico river that flows through the cemetery – because the Headless Horseman can’t cross water.

So here we are… the Headless Horseman and there is Thomas… RUN!!!!!

It was all in good fun. He ended up petting the horse and wasn’t too afraid after all.

The cemetery also has a Beerfest and cider and baked goodies and food so we stayed and filled our bellies before heading off to the next fall adventure.

What a treat! The Sleepy Hollow Cemetery should be a MUST for your Haloween Spooky Fun. There are no jumpy castles or face painting… thank goodness… but just pure cultural references and amazing views and some old history about this country.

Happy Halloween everyone. And if you are ever in Sleepy Hollow… remember RUN for the water if you find yourself face to face with the Headless Horseman.

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