Legend of Sleepy Hollow Scarecrow Contest

Washington Irving profoundly impacted American culture. He is known today for the American folktales found in The Sketchbook of Geoffrey Crayon, Gent., which celebrates its 200th anniversary in 2019-2020. This collection famously contains “The Legend of Sleepy Hollow” and “Rip Van Winkle,” two stories that romanticize colonial life on the Hudson River. The Farmingville Historical Society invites you to participate in this anniversary with our FIRST ANNUAL Legend of Sleepy Hollow Scarecrow Contest.

What is the Scarecrow Contest?

Anyone – families, businesses, students, teachers, community residents- can enter a scarecrow into the contest. The scarecrows must be inspired by the Legend of Sleepy Hollow. The story and character details are outlined below. Our community will cast their votes for their favorite scarecrow. The winning scarecrow will receive a community prize.

How do you enter the scarecrow contest?

You can register online for the contest – click here to register. The entry fee is $25 to enter 1 scarecrow. You must register by October 20, 2020. You can register more than one scarecrow if you choose.

Where and when do the scarecrows get displayed?

The scarecrows must be handed over to the Farmingville Historical Society anytime between October 1, through October 20, 2020. We will coordinate meeting you at the Historical Schoolhouse so you can hand over your scarecrow. The Farmingville Historical Society will hang your scarecrow for display. All scarecrows will be displayed by October 20th before the voting begins. Scarecrows will be displayed on a metal stake.

What should my scarecrow look like?

Your scarecrow should be inspired by the Legend of Sleepy Hollow story – see the story and character details below. It must NOT display any derogatory words, symbols, or nudity. It can display business, family, team, or group names. The Board Members of the Farmingville Historical Society will review all scarecrows before they are displayed to ensure they are in compliance.

Where will the scarecrows be displayed?

All scarecrows will be displayed on the front lawn of the Terry House and 1850 Bald Hill Schoolhouse for everyone to see.

What are the contest dates?

  • Register online by October 20, 2020 – click here to register.
  • Scarecrows will be set up for display from October 1 – October 20.
  • Online voting will take place from October 20 – October 30. Votes will be cast on our website during these dates.
  • The winner will be announced and presented with their prize on October 31, 2020.

What is the winning prize?

The prize is made up of several donations from our local community – food and service gift cards, a basket of chocolate and candy, and a copy of the Legend of Sleepy Hollow book. The prize is designed to support our local community – especially during these challenging times.

The Story of the Legend of Sleepy Hollow

The Legend of Sleepy Hollow is set in 1790 in the countryside around the Dutch settlement of Tarry Town (historical Tarrytown, New York), in a secluded glen known as Sleepy Hollow. In it, lanky newcomer and schoolmaster Ichabod Crane courts Katrina van Tassel, a young heiress who is also being pursued by the Dutchman Brom Bones.

The Legend of Sleepy Hollow Character List

Baltus Van Tassel

Baltus Van Tassel, also known as Balt, is a thriving and contented farmer, father of Katrina, who is perfectly happy within the confines of his farm. He lives abundantly but not proudly.

Brom Van Brunt

Brom, short for Abraham, is Ichabod Crane’s greatest rival in the fight for Katrina’s hand. He is boisterous, burly, and the hero of the area, known for his heroics and feats of strength, for which he earns the nickname Brom Bones. He is especially skilled on horseback. He is mischievous, but he is often motivated by goodwill. He is most likely the one in disguise as the Headless Horseman.

Hans Van Ripper

Hans Van Ripper is a choleric old farmer who is housing Ichabod Crane at the time of the Van Tassels’ party. He lends Ichabod the horse on that fateful night.

Ichabod Crane

A native of Connecticut, Ichabod Crane comes to Sleepy Hollow to work as a schoolteacher and singing master. His erudition and skill at singing are disputed only by the narrator. He is tall and extremely thin with a huge appetite and a certain amount of greed. He uses the rod as his preferred method of disciplining his students—but only on those strong enough to bear it. He is especially interested in ghost stories and the supernatural, because he believes in it. His attempt to woo Katrina Van Tassel fails just before he meets the headless horseman, who is most likely Ichabod’s primary competition in disguise.

Katrina Van Tassel

The only child of a wealthy farmer, Baltus Van Tassel, Katrina is eighteen and universally known for both her beauty and her riches. She is also a flirt, and she always dresses to show off her best features. She is one of Ichabod Crane’s singing students, and she is the object of his desires. Just at the point when Ichabod thinks he has won her over, the narrator suggests that an undisclosed attempt was unsuccessful, which means that Ichabod must leave her house dejected and susceptible to his worst fears.

Summary – The Legend of Sleepy Hollow

“The Legend of Sleepy Hollow” tells the story of Ichabod Crane and his attempt to win the heart and hand of Katrina Van Tassel in the context of a comical ghost story. Ichabod comes to Sleepy Hollow, New York, from his home state of Connecticut, to be the schoolmaster of the village. Sleepy Hollow is a small, very quiet town said to be under some kind of enchantment. Its residents all seem to move a little slower, daydream a little more, and be more prone to believe in the supernatural. Sleepy Hollow has more than its fair share of supernatural occurrences, or at least stories of them.

Sleepy Hollow’s most famous supernatural phenomenon is the ghost of the Headless Horseman, said to be a Hessian soldier who lost his head to a cannon ball during the Revolutionary War. The Horseman is seen most often riding by the church, where local historians say he was buried. He is believed to be always in search of his head. Ichabod is fascinated by this story, being especially interested (and prone to believe) in tales of the supernatural.

Ichabod is a strict teacher but not a cruel one, doling out his punishment of the rod only to those who can handle it. Ichabod makes almost no money, and it is customary in the village for the farmers whose sons he teaches to feed and board him in rotation. Along with this, Ichabod makes some extra money teaching singing lessons—he prides himself greatly on his magnificent voice. This keeps him employed and gives him many opportunities to hear ghost stories from the farmers’ wives and eat meals with the farmers’ daughters. He also has an insatiable hunger and a taste for the finer things.

Katrina Van Tassel, a beautiful young 18-year old woman, is one of Ichabod’s students. She is also the only child of Baltus Van Tassel, one of the more successful farmers in the area. Ichabod is quickly taken in by her flirtatious charms, but it is when he first visits her father’s abundant farm that he considers himself truly in love with her, or at least her likely inheritance.

He quickly sets out to win her hand in marriage, coming by the Van Tassel farm frequently to woo her. 

Ichabod is not alone in his attentions to Katrina. Her beauty, charm, and wealth have entranced many other men in the village, especially the formidable Brom Van Brunt, also known as Brom Bones. Brom is notorious for his boisterous personality, love of pranks, and great skill at horseback riding—all of which make him something of a village hero.

Brom has already scared off many of Katrina’s other suitors, but Ichabod is harder to shake, avoiding physical confrontation with Brom, which is Brom’s main method of intimidation. Without that option, Brom turns to his next best skill—pranks. He fills the school house with smoke, trains a dog to follow Ichabod around howling, and sets many other pranks to frustrate and humiliate Ichabod.

One day, a messenger comes to the schoolhouse to invite Ichabod to a party at the Van Tassels’. At this party, he apparently finds himself the best man in the house, and when the party is over he stays behind. For some reason, however, Katrina disappoints him. Ichabod leaves crestfallen.

Ichabod finds the path home dark and eerily quiet. He tries to keep himself from getting too scared, but soon after he has passed the possibly haunted Major Andre’s tree, he sees a large, dark figure looming nearby. It does not respond to his call, but as he passes by, it starts to move and joins him on the path riding a large, dark horse. Ichabod is greatly disturbed and tries to shake off his pursuer, but he fails. Finally, he notices that the rider has no head on his shoulders; the head seems to be sitting on the saddle in front of the man. Ichabod tries to get his decrepit horse to run home as fast as it can, but he is not a skilled rider and the horse resists.

They end up by the church, the scene of most of the stories of the Headless Horseman, and Ichabod races to the bridge where the ghost is said to disappear and not follow. Ichabod crosses the bridge and looks back, but he sees the Horseman, instead of disappearing, hurl his detached head at him. It knocks Ichabod off of his horse.

The next day, Ichabod’s horse returns to its owner’s farm, but there is no sign of Ichabod. A search party finds hoof prints and Ichabod’s hat, with a smashed pumpkin left next to it. Ichabod is never heard from again in Sleepy Hollow, although later on it seems that he is alive elsewhere and has told his story. Some of the townspeople believe that Brom Bones pulled off a great prank—which put Brom in the final position to marry Katrina—but the old women and local folklore maintain that he was taken by the Headless Horseman.