Book Review: The Legend of Sleepy Hollow by Washington Irving


Another legendary story, another example of how a great idea can transcend time, place and the rules of writing. First published in 1820 as part of a larger collection, The Legend of Sleepy Hollow is a short story that has gone on to overshadow everything else Washington Irving has ever written.

Ichabod Crane is a teacher from Connecticut (where all teachers at the time are from apparently), educating the children of the Dutch farmers in New York and accepting their hospitality – he doesn’t have a place of his own and bunks in with anyone willing to offer him a place to sleep so he moves around quite a bit. To remedy his lack of fortune, he has his eye on the attractive daughter of a local wealthy man but the Headless Horseman – the legend referred to in the title – has his eye on Ichabod (well, maybe not his eye since he doesn’t have any but you know what I mean).

The story is told from the perspective of someone named Diedrich Knickerbocker with a note at the beginning of the story and a postscript describing how it was found in his papers after his death. This is an interesting device because I kept wondering who Diedrich Knickerbocker was and why he was so interested in this story, so much that it detracted from my interest in the story of Ichabod. But that is part of the story’s brilliance. It feels like so much is left explicitly unexplored so that readers wonder about the importance of what they aren’t being told.

It’s also one of those stories that high school English teachers can analyse until they go crazy. Is it a commentary on fear? Is it a commentary on the outsider, the other? Is it a commentary on greed? Ichabod Crane’s desire for Katrina Van Tassel seemed just as much a desire for the material things her father’s wealth could provide him and when she eventually turns him down, it seems like his just deserts (although it’s a stretch to say he deserved his other fate as a victim of the Headless Horseman).

For the rest of us, we can just focus on the creepiness of the premise as we are left to wonder what really happened, whether the Headless Horseman truly existed or whether the legend was simply exploited for its benefits.

The story is a perfect example of telling rather than showing in breach of the “show, don’t tell” rule but it’s also an example of how it can sometimes work. Still, it could have worked a little better. There’s only one line of dialogue in the entire book and dialogue is how long tracts of prose get broken up for the reader’s relief. And yet for a story to have resonated for this long, there’s got to be something to it.

As with many older stories, I feel it could do with a little bit of editing but it’s a nice blend of plot and well-executed writing. The characters aren’t that well developed but it contributes nicely to the sense of mystery, sort of a Blair Witch of its time.

Some people say that all the stories have been told now and the new ones are just variations on the originals. Well, this is one of the originals. Enjoy.

3 stars

*First published on Goodreads 20 December 2016


2 thoughts on “Book Review: The Legend of Sleepy Hollow by Washington Irving

  1. I’ve been a big fan of this story since rereading it as an adult several years ago. I do take exception with one point of your review. I feel Rip Van Winkle is the “lasting” tale from W Irving. LOVE that one. I must have read a condensed version to my kids 200 times when they were small.


    • I’ll concede that Rip Van Winkle is a part of his legacy that I overlooked but I’ll stand by The Legend of Sleepy Hollow being the most lasting in my perception because it’s the Irving story that I read during my formative adolescent years. I guess it’s all about individual experience – and isn’t that reading in a nutshell? Thanks for reading, Jeff! 🙂

      Liked by 1 person

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