Halloween at Sleepy Hollow

New York, Cemeteries, CGT SocietyJ.R PepperComment

When spooks have a midnight jamboree, 
they break it up with fiendish glee. 
Now, ghosts are bad, 
but the one that's cursed 
is the Headless Horseman, 
he's the worst... 

Sleepy Hollow

My poor mother had to listen to this song countless times when I was a kid. It’s from Disney’s The Legend of Sleepy Hollow and regardless what time of year it was, it  echoed through the bones of my childhood home. 

It wasn’t until years later that I would finally travel to the actual Sleepy Hollow in Tarrytown New York.  A quick hour or so from Grand Central Station and you wind up in this quite literal sleepy lil' town. For obvious reasons, I highly recommend a visit over there around Halloween, not only for the beautiful brilliant hues of fiery-orange fall, but an opportunity to see a town that embraces All Hallows Eve and all its haunted glory.


When I went, dozens of handmade scarecrows were added to every light post on the main road.

In addition, there is a devilishly cool pumpkin-head scarecrow taking over the town's center. You will also find many of the shops adorned with pumpkins, corn stalks and of course, the occasional eerie headless horseman.

Any Creepy Girl Traveler is going to want to head up to the cemetery, and believe me it’s worth the trip! TIP: to all my heel sporting sisters- the walk from the train to Sleepy Hollow is basically up hill all the way. The cemetery itself really isn’t path friendly- so be prepared to get your cardio for the day. 

The tall cemetery gates will greet you at the top of your climb. If it’s on the weekend there will also be a small table of Sleepy Hollow merchandise. All proceeds go to the local historical society- so don’t fret buying that Sleepy Hollow coffee mug.

Fall Color New England Cemetery

Sleepy Hollow Cemetery is- in a word- gorgeous. Its undulating hills make it an incredibly picturesque New England cemetery. If you visit in the fall, you will be just as dazzled by the myriad of colors that surround the gravestones as the monuments themselves. 

Sleepy Holloe Gravestone

If you are like me with my interest in the Washington Irving story- you’ll begin noticing a number of names on the graves.

The most obvious of course is Washington Irving’s grave surrounded by an ornate black gate, which is also designated as a historical landmark. You’ll also notice several graves belonging to the Van Tassel family, the famous family from Irving’s story. I was admittedly; way more excited to find out about this then my traveling companion. 

Contrary to popular belief, the Tim Burton Sleepy Hollow was not filmed here- but there are a few features of creepy-worth that were. In 1989, The Ramones filmed their music video “Pet Sematary”1- burying the band mates alive. For those on the Gothic-side- Sleepy Hollow is also the place to Barnabas Collins of House of Dark Shadows. Who could blame them? The cemetery is awe-inspiring. The view is amazing and monuments are among some of the most dramatic I’ve seen in the States.

Lister Grave

The most stunning view is the monument to Edwin Lister, which is attended a beautiful woman eternally mourning at his grave. 


You can always casually wander the cemetery on your own, but there are of spookier options. Sleepy Hollow Cemetery offers a variety of tours (reservations required on their site, but I have to recommend the lantern tours. These evening tours are offered on Saturday night from 9:00pm until 11:00pm rain or shine. If you have to pick one- choose the Murder and Mayhem tour. The MAP link: HERE


Aside from the tours, the cemetery also offers a variety events throughout the year- all of which are detailed on their website. They also offer spectacular fantastic, albeit expensive Night Photography Workshop. Sleepy Hollow has dozens of Halloween themed events, as All Hallows gets closer, including a fabulous Jack O’Lantern blaze.


There are a variety of places to eat in nearby Sleepy Hollow. Highly recommended? Lefteris Gyro at 1 North Broadway- for tasty, and plentiful plates of awesome Greek food. If you are looking for a brew after your hill-filled cemetery walk try the Bridge View Tavern at 226 Beekman Avenue with its multiple taps. 




I currently live in Brooklyn, New York with her dog and guinea pig and calls Tulsa, Oklahoma her second home.


I am photographer and docent at the Morbid Anatomy Museum.


I'm an avid antique photography and oddity collector. I'm also a huge researcher of Victorian Spiritualism, and my 'ghost' photos have been featured in a few shows and publications. 


Pretty much every vacation I've had has had an odd component to it. I have stayed at the Lizzie Borden Bed and Breakfast last year, The Mutter Museum is one of my favorites and I even made one of my exes drive all the way the hell out to Area case you were wondering, we saw more cows then anything else.

WHY CGT SOCIETY: I'm thrilled that I'm meeting all these macabre and creepy ladies lately!!

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Sleepy Hollow Cemetery