POINTS FOR DISCUSSION
The Legend of Sleepy Hollow

Contrast Brom Bones and Ichabod Crane (actions/physical appearance)
The description of Ichabod on page four gives many good physical details. His awkward, skinny body which
makes him look like a scarecrow is a dramatic contrast with the “burly, dashing” Brom Bones whose
appearance and general behavior are described on page 19. Students should look at how Brom and his “gang”
are always looking for fights and fun. He is physical, rather than intellectual and appears most interested in
having a good time, whereas Ichabod takes himself and life in general much more seriously.
Ichabod:
Book smarts
Lanky and weak
Not from the area; doesn't understand the "locals"
Lets his imagination get away from him
Believes in ghosts
Wants to marry Katrina for the wrong reasons
Not athletic or good at riding horses
Brom Bones:
Very strong
A lot of friends
Street smarts
From the area; knows every inch of Sleepy Hollow
Likes to play pranks
Knows he has to find other way of getting rid of Ichabod other than fighting
him out in the open
Athletic and highly skilled at riding horses

Cite evidence of Ichabod’s active imagination
1. He loves ghost stories and takes great interest in alarming stories
and unusual facts.
2. After spending time reading, listening, or telling tales, everything
he sees and hears seems to come to life—he sees and hears things
while he walks home in the dark.
3. His active imagination also makes brings his fantasy of great
wealth to life.
4. When he sees the animals on the Van Tassel’s farm, he vividly
pictures them as various delicious dishes of food.
5. He can also clearly imagine his future with Katrina.
Although tales were a common way to spend long evenings entertaining
themselves, Ichabod seems to have an especially great interest in alarming
stories (“no tale was too monstrous for him” (p.11)) and unusual facts (“the
world turns round and that half the time they were topsy-turvy”(p.13)). After
spending time reading, listening to, or telling tales, everything he sees and
hears seems to come to life on his walks home in the dark (p.11-14). That is
why he is so frightened at the end and so willing to believe that it was indeed
the headless horseman that he has encountered. The other field in 40 which his
imagination is given full sway is in his fantasies about owning great wealth.
When he sees the animals on Van Tassel’s farm, he vividly pictures them as
various delicious dishes of food (p.17). He also had a very clear image of his
future with Katrina (p.17-18).

Importance of the title: The Legend of Sleepy Hollow
Legend: A story from the past that is believed by many people but cannot be
proven true
By calling the story a legend, Irving makes the reader aware that it is believed by many people, but
cannot be proven true. We as the reader now that the story is not proven true.
Sleepy refers to the setting of the story and the behavior of the people in the
town. It’s a sleepy, little town where nothing really happens and people spend
their time dreaming. It is very enchanted and has a comfy, cozy feel to it.
Hollow is a term used to describe towns in the Appalachian states. That means
we know right off the bat that it is an American story that takes place on the
East Coast.
So why does Washington Irving choose this title? Because, “The Legend of
Sleepy Hollow” is a story about a place, it’s not about Ichabod, it’s about
Sleepy Hollow. Irving wants us to know that before we even turn the first
page. It is a story that has not been proven true or false about Sleepy
Hollow.

Conflicts in The Legend of Sleepy Hollow
Man vs. Self: Ichabod is in conflict with himself because he is so
superstitious. He needs to overcome his own fears and needs to come to
terms with what is real and not real. His superstitious self is what lead to
his own demise.
Man vs. Man: Brom Bones plays pranks on Ichabod to get him to stop
trying to get Katrina. Bones tells a scary story of the Headless Horseman
in Sleepy Hollow, and tried to scare Crane off after the party.
Man vs. Nature (Ichabod Crane V.S. Sleepy Hollow) Ichabod Crane
began to take his fears in as reality and was frightened by anything around
him. From trees to bushes, from grass to branches.

Themes in The Legend of Sleepy Hollow: Central ideas within the text
Greed and Gluttony- Excessive eating
1. “Ichabod Crane had a soft and foolish heart towards the sex; and it is not to be
wondered at, that so tempting a morsel soon found favor in his eyes; more
especially after he had visited her in her paternal mansion.”
Allow us to translate: it was love at first sight—or actually, love at first sight of
her bank account. Ichabod is greedy! He becomes head over heels for Katrina only
after seeing her father’s house and her inheritance.
2. “The pedagogue's (teacher’s) mouth watered, as he looked upon this
sumptuous promise of luxurious winter fare. In his devouring mind's eye, he
pictured to himself every roasting-pig running about with a pudding in his
belly, and an apple in his mouth; the pigeons were snugly put to bed in a
comfortable pie, and tucked in with a coverlet of crust; the geese were
swimming in their own gravy; and the ducks pairing cosily in dishes, like snug
married couples, with a decent competency of onion sauce. (1.22)
Ichabod fantasizes about wealth and eating to great excess
3. “As the enraptured Ichabod fancied all this, and as he rolled his great green eyes over the fat meadowlands, the rich fields of wheat, of rye, of buckwheat, and Indian corn, and the orchards burthened with
ruddy fruit, which surrounded the warm tenement of Van Tassel, his heart yearned after the damsel who
was to inherit these domains, and his imagination expanded with the idea, how they might be readily
turned into cash, and the money invested in immense tracts of wild land, and shingle palaces in the
wilderness.”
In case you were thinking that Ichabod was just greedy for food, he very
quickly clears that up for you here. He is both greedy for food and the material
wealth that he hopes to get in marrying Katrina.
The supernatural
1. “A drowsy, dreamy influence seems to hang over the land, and to pervade the
very atmosphere. Some say that the place was bewitched by a high German
doctor, during the early days of the settlement; others, that an old Indian chief,
the prophet or wizard of his tribe, held his powwows there before the country
was discovered by Master Hendrick Hudson.”
Right away, we're told that something fishy/mystical is going down in Sleepy
Hollow.
2. “Another of his sources of fearful pleasure was, to pass long winter
evenings with the old Dutch wives, as they sat spinning by the fire,
with a row of apples roasting and spluttering along the hearth, and
listen to their marvelous tales of ghosts and goblins, and haunted
fields, and haunted brooks, and haunted bridges, and haunted houses,
and particularly of the headless horseman, or galloping Hessian of the
Hollow, as they sometimes called him.”
The natural and the supernatural seem pretty cozy in "Sleepy
Hollow." You know, cooking, sewing, and telling ghost stories—The
towns people find entertainment in sharing ghost stories.
 Warfare: Revolutionary war—love is a battlefield
1. “When he entered the house the conquest of his heart was
complete.”
Love = battlefield.
2. “Ichabod, on the contrary, had to win his way to the heart of a
country coquette, beset with a labyrinth of whims and caprices, which
were forever presenting new difficulties and impediments.”
Hitting on a girl seems to be more dangerous than fighting a dragon
for our Ichabod.
3. “To have taken the field openly against his rival would have been madness; for he was not a man to be
thwarted in his amours, any more than that stormy lover, Achilles.”
 Symbols in The Legend of Sleepy Hollow: the use of one thing to
represent another
1. Hessians: German soldiers who were hired to work for the British
during the American Revolution. There were many of them and
they were trained to fight—based on their training and amount of
them, there was a very good reason to be scared of them.
2. Ichabod’s never ending hunger is a symbol for his greediness—
even if he were to get Baltus’ wealth, chances are he still would
not be satisfied.
3.
Ichabod sings psalms in order to calm his nerves, on the night
of his meeting with the headless horseman he is unable to sing,
what does this symbolize? Symbolizes that the apparition may be
real, or that something is different this time.

How would the story of "Sleepy Hollow" have been if it were written from Katrina's point of view?
Would the ending still be the same? OPINION
 Would you recommend the story to a friend? Would you read other works by Washington Irving--based
on your reading of this story? OPINION