The Boys of Sleepy Hollow

Near the beginning of the story, Irving describes the secluded little valley known as Sleepy Hollow and the descendants of the Dutch families who live there. Then he tells us that the “rustic lads” of the valley are known throughout the surrounding countryside as the Sleepy Hollow Boys.

And among those boys, Irving introduces the most formidable of them all: Abraham Van Brunt. Better known as Brom Bones.

Suddenly, Brom becomes more interesting. Because Brom isn’t simply the handsome, troublesome rival standing between Ichabod Crane and Katrina Van Tassel. He belongs to Sleepy Hollow. More importantly, he belongs to a group of young men who are already part of the social fabric of the place.

Brom is their most prominent member. He’s the local horseman, prankster, fighter, and troublemaker. Irving describes him as someone always ready for either a fight or a frolic, a young man known throughout the countryside for his strength, horsemanship, and mischief.

And Brom has his own smaller circle within the larger group of Sleepy Hollow Boys. Irving gives him three or four close companions who follow his lead as they ride through the countryside looking for amusement or trouble. When their horses thunder past farmhouses in the middle of the night, everyone knows exactly who is responsible: Brom Bones and his gang.

Ichabod Was the Outsider

And that made me look at the story a little differently. Ichabod Crane doesn’t belong to Sleepy Hollow. He has come from Connecticut to teach the local children. He moves among the families, teaches singing lessons, attends gatherings, listens to their ghost stories, and eventually begins courting Katrina. But he is still an outsider.

Brom isn’t. Brom grew out of the place. He knows its roads and farms, its people and customs, its horses and stories. When the community gathers at the Van Tassel farm, Brom is already part of the world Ichabod is trying to enter.

That makes their rivalry about more than Katrina. It’s also a conflict between the outsider and the man who belongs. And perhaps that’s one reason the final chase works so well. By the time Ichabod rides home alone through the darkness, he’s traveling through a landscape filled with stories that belong to the people of Sleepy Hollow.

Stories he’s spent the evening eagerly listening to. Stories Brom Bones knows just as well. Including the story of the Headless Horseman.

Every Town Has Its Stories

As a writer, this is the detail I love most. Irving didn’t simply invent a ghost and send it chasing a frightened schoolmaster through the woods. He created a community.

There are old Dutch families and farmers, young women and young men, storytellers and gossips. There are local legends everyone knows. There are places people avoid after dark. There are stories that have been repeated so many times that nobody quite remembers where truth ends and embellishment begins.

And there are the Sleepy Hollow Boys. The young men who grew up there. Who know one another. Who ride together. Who cause trouble together. And who understand the stories and secrets of their home in a way an outsider never could.

It’s something writers of small-town fiction still do today. Because a fictional town becomes real not when we draw its streets on a map, but when we understand the relationships among the people who live there.

Who belongs?

Who doesn’t?

Who has known everyone since childhood?

Who knows the old stories?

Who knows which stories aren’t true?

And who might have a very good reason for making sure the newcomer believes them anyway?

More than two centuries after Washington Irving wrote The Legend of Sleepy Hollow, we’re still asking those same questions. And that’s why I keep returning to old stories. This time, I went back to Sleepy Hollow looking for ghosts. Instead, I found the boys who lived there.