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  • Writer's pictureMarsha

Halloween at the Headless Horseman's haunt

Halloween. The night when the veil between worlds is thinnest. It's important to chose wisely where you'll spend this spookiest time of year.


For us, it was Sleepy Hollow, home of the Headless Horseman.

Halloween or no, it's worth spending time in this charming New York town. When you're famous for something, you might as well embrace it...and this place does. Washington Irving's legendary horseman imbues every aspect Sleepy Hollow.


From the street signs...

To the fire department...

...you can't miss who's the most infamous resident around.

Even if you're a Washington Irving aficionado, take some of the tours offered. The guides are knowledgeable and entertaining and they're a great way to delve deeper into the local history.


We took a candlelight tour of the Sleep Hollow Cemetery Friday night and a tour of its neighbor, the Old Dutch Church and cemetery the following morning.


I was expecting the candlelight tour to be spooky. Walking around in an old graveyard in the dark during scattered light rain showers with only an oil lamp for light has some promises to live up to.

It wasn't spooky but it was a great time. We saw numerous mausoleums lit up against the darkness, varying in stature, standing vigil against time and raiders protecting their inhabitants. Even those without the funds to erect such monuments to their wealth and power have gorgeous tombstones and grave markers. The atmosphere was more surreal beauty than night terror.


The Old Dutch Church, founded in 1685, houses the cemetery made famous by Washington Irving's legend (which is not the more elaborate one we visited the night before. They are two separate places), has simpler and older gravestones dating back to the Revolutionary War.

It was a fortuitous, if unplanned, arrangement of walking tours as the information gleaned that grey overcast morning built upon the knowledge from the previous evening giving us a better understanding of the town.

There's more to Sleepy Hollow, and its neighbor Tarrytown, than a single indominable spirit though. Dressed in our Steampunk finery for the weekend, we strolled around the farmers market in the town park after our tour and I must say, tying strangers to the fence was an old fashioned warning we heeded...and stayed well-behaved.

No trip of ours would feel right if we didn't take time to wander aimlessly around in search of...anything and nothing. Our random exploration let us catch a glimpse of the Armour-Stiner (Octagon) House. Built in the 1860s, it replicates Donato Bramante's 1502 Tempietto in Rome. Rome's Tempietto is supposed to be the site of St. Peter's martyrdom. Once owned by the National Trust it's now a private residence with limited tours. Limited tours require preplanning. Our cap of which had been reached with the morning's lecture outing.

The Lyndhurst Mansion on the other hand had explore the house and grounds on your own terms available and not too many people, so we did.


This stunning gothic revival style mansion was built in 1838 and if you love architecture and historical furnishings, it's a must see. The woodwork, the ceilings, the stained glass, the artwork. All are breathtaking.


But the Sleepy Hollow cemetery called us back on All Hollow's eve to see how it appeared in daylight (not surprisingly, the cemetery is closed in the evenings except for the tours). Cemeteries on the east coast never seem to disappoint with their timeworn and often elaborate headstones.

What about the famous covered bridge from Irving's legend?

It doesn't exist.

There are several that say they are in the same spot or are replicas of what would have existed during Irving's time including a well known one in the Sleepy Hollow Cemetery...if you need pictures of a bridge like we did.

Halloween evening itself was perfect. The clouds had passed by, the temperature was one of a crisp autumn day without being too cold. The pandemic may have prevented several of the normal festivities from occurring but there where enough people milling about to make it feel like Halloween without actually fearing for your life. And almost all of them where in some level of costume! There was live music in a couple of places and an overall mood of fun.


You gotta love the Headless Horseman's Haunt.

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