5 Best Movie Adaptations of the Hudson Valley’s Headless Horseman

If you live in the Hudson Valley, there's virtually no way you haven't heard about the legend of the Headless Horseman. To be frank, when it comes to legends and tales that make the hair on your arms stand at end or send a chill up your spine, the legend of the Headless Horseman ranks high on just about any list.

History of the Headless Horseman

If you haven't heard the legend of the Horseman before, here's a little history for you. It is said that the Headless Horseman to this day haunts the Hudson Valley village of Sleepy Hollow. His legend began over 200 years ago when famous author Washington Irving wrote his famous story "The Legend of Sleepy Hollow" in 1820.

Though Irving wrote The Legend of Sleepy Hollow it's origins date back even further back in time. The most known story about Headless Horseman and his origin dates back to Revolutionary War times.

It's said that the Horseman was a casualty of war and had his head blown off by cannon fire. The identity of the Horseman has never been confirmed beyond a reasonable doubt but most say he was a Hessian Soldier.

What Inspired the Legend of the Headless Horseman?

The Hessian Soldiers were more or less a group of mercenaries of German origin who came to America to reinforce the British in their war effort. Some stories say that it was not a Hessian Soldier but an American soldier who lost their head on the battlefield but either way the legend goes the Horseman haunts the land in search of his missing head.

Celebrating the Headless Horseman on the Silver Screen

The thing with legends like that of the Headless Horseman is that over the decades and in this case centuries, the story tends to re-told a time or two. In those retellings, many like to pay homage to the legend and the history and other cases, some like to add their own unique twists.

With over 200 years of time having gone by since the legend began, many have created their own iterations of the story and many of those iterations have been featured on television and in movies, so without any further adieu, here are some movies you can watch this Halloween season in honor of the legend himself...

5. Headless Horseman: The Final Cut

Many of you out there like myself probably remember that not to long ago the SYFY network aired a number of straight to TV movies. To be blunt, most of these movies never had a snowballs chance in hell at winning a major award, however many of them of them were and are fun watches that were worth about 90 minutes of your time.

That's exactly what we have here with Headless Horseman: Final Cut. It starts out like many slasher-type horror films, with a group of teenagers eagerly making their way to an "epic party". And also not uncommon in movies like this, the group of teens hits some car trouble while trying to take a short cut while traveling to the party.

The teens land in the middle of nowhere town called "Wormwood" and while their, the spirit of the Headless Horsemen begins to hunt them down one by one.

4. The Hollow

Next up on our list we have "The Hollow". The movie debuted in 2004 and like our last entrant also involves a group of mischievous teenagers looking to have some fun, cause a little trouble and maybe pull off a prank or two before Halloween.

Things however don't exactly go according to plan though when , you guessed it, the Headless Horseman arrives on the scene and causes havoc. Also, for fans of the massive successful comedy "The Big Bang Theory", it's an opportunity to see star of the show Kaley Cuoco before the Big Bang fame.

3. Headless: A Sleepy Hollow Story

This is our first entrant on the list that takes the legend of Sleepy Hollow and the Headless Horseman and...turns it on its head....

Okay bad jokes aside, this is a series that I just came to learn of while researching the best shows and movies about the Headless Horseman. It is a modern day series available to watch on YouTube that gives the legend it's own quirky and comedic twist.

It starts central character Ichabod Crane coming to the Sleepy Hollow as he's beginning his new chapter as teacher at a local school. He's hit with quiet the rude awakening though when he meets his new landlord who raises his rent astronomically just because he was a few minutes late to their meeting.

Ichabod must now figure out a way to be able to afford his newly increased rent price, so he does what many do and puts out a flier looking for a roommate. Who better to answer that call than the Headless Horseman. Now I have only watched the first episode myself and now plan on watching the remaining 15, but from what I gather the goal is to help the Horseman find his head. How the Horseman will help with paying rent, I don't know, I haven't gotten that far yet.

2. Sleepy Hollow: TV Series

The next addition to our list is television series quite frankly I couldn't believe debuted on televisions across America over a decade ago. It's Sleepy Hollow the television series. The show originally aired on FOX from 2013-2017 and had four seasons for a total of 62 episodes.

The show is the perfect combo of crime thriller meets the world of the supernatural. In this rendition, the character of Ichabod Crane awakens from the dead after 250 years and must team with a Detective to solve a murder dating back to the Revolutionary War era.

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Rising from the dead with Crane though is the Headless Horseman and in this version the Horseman is not just a spirit but rather one of the infamous Horseman of the apocalypse. Crane and Detective Abbie Mills along the way fight a number of other supernatural phenomena and stop the vicious cycle of evil.

1. Sleepy Hollow

I mean come on now...did you really expect anything else to be number 1 on a list like this? Our final entrant on this list is non other than the wildly popular and beloved film from the mind of the one and only Tim Burton...it's Sleepy Hollow.

The movie starred Johnny Depp as Ichabod Crane, Christina Ricci as Katrina Van Tassel and Christopher Walken as the Headless Horseman himself.

There's not much to say about the film other than it is without much argument, the definitive Hollywood telling of the famous tale. Many people hear the name Headless Horseman and think of this movie.

That brings this little countdown to an end. Happy Halloween, hope you enjoy the holiday binge watching, I know I will.