Why Sleepy Hollow is A Great, book, movie and Destination
I love Fall and Halloween. There’s just something about that time of year when the leaves change and a chill is in the air that is cozy and familiar. As a young kid I first saw the Disney animated short “The Legend of Sleepy Hollow” in school on Halloween and I was hooked. So get comfortable by your fireside in your favorite flannel shirt, pour yourself a warm drink and let’s discuss why this American classic is a Jay’s Faves.
Book
Let’s start at the beginning…the book, or more accurately, the short story. Either way, Washington Irving put quill to paper and in 1820 came up with “The Legend of Sleepy Hollow;” A story about a new, albeit awkward, school teacher, Ichabod Crane, who comes to the quiet glen and fast learns of the town’s reputation of ghosts, goblins and, of course, the Headless Horseman!
Irving paints a beautiful picture of Fall in the Northeast and you can almost feel the chill and dread in the air by the time the Headless specter shows his face, or um, doesn’t show his face, but shows up.
Fun fact, Washington Irving lived for a time in Sleepy Hollow, then just known as Tarrytown, and borrowed extensively from the actual surroundings for inspiration for his chilling tale (see more below about the Old Dutch Church and the famous bridge). Irving can still be found in Sleepy Hollow as his remains were buried in the Sleepy Hollow Cemetery.
Media
The story of Sleepy Hollow struck a chord with many folks and has continuously been retold in various formats for over 200 years now. It seems as soon as some new entertainment medium is created, a presentation of Sleepy Hollow in that medium is soon to follow and the classic tale has been presented in just about all media formats. The first movie was “The Headless Horseman, a silent film from 1922 that starred Will Rogers.
There have been many other movies and made for TV specials – one even starring Jeff Goldblum from 1980 – but perhaps the most popular movie to date is the 1999 adaptation by Tim Burton. This movie is wonderfully atmospheric, however not fully true to the original story, changing Ichabod Crane from a school teacher to a constable.
My personal favorite is the 1949 Disney animated short “The Legend of Sleepy Hollow.” This was played on TV every year. But back then you’d have to make sure you knew when it was airing as it was played once and there was no way of recoding it (yes I’m old).
The animated short is amazingly drawn by those excellent Disney cartoonists, paying attention to every detail. It’s narrated by famous crooner Bing Crosby, who also sings a couple of catchy tunes as well.
As mentioned above, the Disney short was also played in my school every Halloween while I was in Elementary School. You knew it was a special day when the teacher brought out the projector. Then, after lunch, we’d put our costumes on and each class would parade through the other classes. Basically, this was one of the best days of the school year and little work was accomplished that day as we’d all be anticipating that night’s trick or treating.
Sleepy Hollow has also been brought to the stage numerous times and been the subject of podcast retellings. I just recently was present for a taping of a telling of the story by some wonderful actors in studio, which will be broadcast on WBFO, a local radio station in Buffalo, NY.
The Village
As Washington Irving says in the opening of his novel, “In the bosom of one of those spacious coves which indent the eastern shore of the Hudson, at that broad expansion of the river denominated by the ancient Dutch navigators the Tappan Zee, and where they always prudently shortened sail and implored the protection of St. Nicholas when they crossed, there lies a small market town or rural port which by some is called Greensburgh, but which is more generally and properly known by the name Tarry Town…From the listless repose of the place and the peculiar character of its inhabitants, who are descendants from the original Dutch settlers, this sequestered glen has long been known by the name of “Sleepy Hollow”…”
I’ve been to Sleepy Hollow twice now and plan to make another trip there soon. Interestingly, the village officially changed its name to “Sleepy Hollow” in 1996 – previously being known as North Tarrytown – and has since fully embraced Irving’s story, to the point that the local high school football team is called “The Sleepy Hollow Horsemen.”
While I’m sure Sleepy Hollow is a nice place to visit year round, it really shines in Autumn. They smartly play up to their roots and there are many wonderful tourist attractions. First, no visit to the Hollow is complete without a visit to the Sleepy Hollow Cemetery. Here you will find where Washington Irving was laid to rest, as well as the Old Dutch Church that Irving describes in his story and where the Horseman is said to be seen.
At certain times you can get tickets to hear a reading of Sleepy Hollow in the church, spooktacular indeed!
When visiting the old church, make sure to stop by the bridge close by that is marked by a sign indicating that it’s the spot of the old bridge that Ichabod crossed to make his escape.
Another fun time is The Sleepy Hollow Experience. Walk around Washington Irving’s New York estate where at each stop you will be treated to actors playing out a part of the story, until the Headless Hessian comes storming by on horseback! This may be a tad intense for the little ones.
Hands down one of the most popular Fall events at Sleepy Hollow is the Great Jack O’Lantern Blaze.
Visitors will walk along the grounds of the Van Cortlandt Manor and witness over 7,000 carved craft pumpkins that have been formed to make various sculptures, from a train to a dragon.
And don’t forget the annual Halloween parade for some wholesome family fun. The parade kicks off from Patriot’s Park at 5pm and makes its way to Main Street, where the party continues with live music, food vendors and street performers adding to the festivities.
If you are going to give Sleepy Hollow a visit, make sure to book your room and get your event tickets well in advance. The events sellout quickly and the rooms book up fast in the Fall. It is not unusual to have some of the events sellout months in advance!
This Fall do yourself a favor and give Sleepy Hollow a read, watch or go visit that “Moonlit Town.” You won’t be disappointed. Happy Fall and Halloween. Boo!!
More Of Jay’s Faves
Check out the below, if interested in more of Jay’s Faves.
“How boring would the world be if everywhere and everyone were the same. Safe travels and good adventures.” Scuba Jay