Writers Reading: Halloween Edition: The Legend of Sleepy Hollow by Washington Irving

Writers Reading:

Halloween Edition:

The Legend of Sleepy Hollow


Washington Irving


quidor_sleepyhollow“Certain it is, the place still continues under the sway of some witching power, that holds a spell over the minds of the good people, causing them to walk in a continual reverie. They are given to all kinds of marvellous beliefs, are subject to trances and visions, and frequently see strange sights, and hear music and voices in the air.” –Washington Irving


I can’t remember when exactly I started the tradition of reading The Legend of Sleepy Hollow every year at Halloween, but I think it started sometime in the seventh grade. My middle school had just opened a brand new library and I was scouring the stacks when a well-worn copy of Washington Irving’s classic caught my eye.

I was immediately swept up in the language and style of the novella, everything about it was enchanting and it was very easy for me to get transported to the small, mystical hamlet of Tarrytown. Irving lovingly describes each glen and brook, enamored by the beauty of New England. He weaves a great American folklore, an homage to a place in time that has since dissolved into history books. The Legend of Sleepy Hollow is both a folk tale and a time capsule, a classic in English literature that stands the test of time.

While it’s not very hard to see why The Legend of Sleepy Hollow is constantly adapted, I’m a stickler for the classic. Whereas today, Ichabod Crane is portrayed as a GQ-esque sex symbol (e.g., Tom Mison and Johnny Depp, respectively), Irving portrays Ichabod as an unattractive antihero:

“To see him striding along the profile of a hill on a windy day, with his clothes bagging and fluttering about him, one might have mistaken him for the genius of famine descending upon the earth, or some scarecrow eloped from a cornfield.”

Ichabod isn’t much of a standup guy, either. His intentions with the heroine Katrina Van Tassel are less than honorable. Because Katrina’s father is the wealthiest man in Sleepy Hollow, Ichabod makes it his personal mission to schmooze his way into their lives. The brawny Bram Bones is wise to Ichabod’s sleazy act and while they have a few skirmishes through out the story, none beats the Halloween party when Bram tells the story of the headless Hessian general who haunts the bridge adjacent to the Old Dutch Burying Ground. Shortly thereafter the Halloween party ends and Ichabod is thrust back into the cold October night. He and his horse Gunpowder, must trot along under cover of darkness back to their house, alone and afraid. In time, Ichabod reaches the infamous Dutch Burying Ground adjacent to the old covered bridge, and that’s when the terror happens.

“The hair of the affrighted pedagogue rose upon his head with terror. What was to be done? To turn and fly was now too late; and besides, what chance was there of escaping ghost or goblin, if such it was, which could ride upon the wings of the wind? Summoning up, therefore, a show of courage, he demanded in stammering accents, ‘Who are you?’ He received no reply. He repeated his demand in a still more agitated voice. Still there was no answer.”

The Headless Horseman is undoubtedly one of the most terrifying classic villains in horror canon. Granted he might not be as scary as Pennywise the Clown, but it would still be terrifying to meet an immortal, decapitated Hessian solider in the woods. Through his polished storytelling and signature style, Irving kicks up the level of terror by using apt descriptions of the monster stalking Ichabod. The reader gets absorbed by the expertly written acoustics and the terror Ichabod experiences as he slowly realizes he’s doomed to meet his fate.

The story ends with a brilliant and ominous postscript, setting the bar high for all other horror stories to come out of North American literature forever. If you haven’t yet, read The Legend of Sleepy Hollow and see why it’s stood the test of time.


The Legend of Sleepy Hollow and Other Stories


Washington Irving

Penguin Classics; Reprint edition (September 30, 2014) 

400 pages