The Legend…and the Reality, of Sleepy Hollow

I work in Tarrytown, which is in Westchester, just north of the Bronx. In 1996, North Tarrytown had its name changed back to its original, and much more famous, former moniker of Sleepy Hollow. When I found this out, I became desperate to come back to Westchester on a weekend so I could go and see the places made famous in Washington Irving’s The Legend of Sleepy Hollow, and this past weekend, with sunny skys and autumnal foliage, the timing was just perfect. The day before we went, I read The Legend of Sleepy Hollow for the first time. Having only known the story from the Johnny Depp film, I was expecting something frightening and bloody – how wrong I was!  Hollywood strikes again! The original tale couldn’t be more different, and is more of a love letter to the small, traditional Dutch community that once lived here, and the legends and tales belonging to the sleepy, wooded glen on the banks of the Hudson where they had chosen to settle. The power of suggestion and imagination is very prominent in Irving’s tale, and it’s pretty clear that the Headless Horseman exists only in the projected fears of the inhabitants’ minds, rather than in reality. However, as I found out during my day at Sleepy Hollow, there really was a headless horseman, and a Katrina Van Tassel (several of them, actually, as Van Tassel was the equivalent of the surname Smith in the area), and current inhabitants of Sleepy Hollow are no less enamoured with the legends of the area as their predecessors were.

My tour of Sleepy Hollow began at the Old Dutch Church and Burial Ground, which is a pretty flint church with lovely windows and duck egg blue interior that dates back to the 1600s. It was this church that Ichabod Crane taught his choirboys in, and where the Headless Horseman was buried and rose from for his nightly rides. Now the church is on a busy main road, but at the time, it was situated at the curve of an old post road, and surrounded by countryside. To the East of the church is the burial ground, filled with many beautiful, 18th and 19th century graves, many in Dutch, and all with fantastic carvings. Every other grave is that of a Van Tassel, and the tour guide explained how many families intermarried, and so most people in the graveyard were related to each other either by blood or by marriage. In the middle of the graveyard is an empty patch where no graves have ever been dug; legend has it that this is where the Headless Horseman was buried. The Headless Horseman was a real man; a Hessian soldier hired by the British to fight the Americans, he was beheaded in the battle of White Plains. The local people allowed him to be buried in the church yard because, legend says, he rescued the small daughter of a local family whose house had been burnt down by the British soldiers. This favour was remembered, but not to the extent that he was allowed a headstone. Over time this story developed into a legend about the Headless Horseman riding out at night to reclaim his head, though the tour guide couldn’t say whether anyone had seen him recently!

Right next to the old burial ground is the cemetery, which houses many more graves, mainly from the 19th century. This is where Washington Irving is buried, along with other American luminaries such as Andrew Carnegie and Elizabeth Arden. On Saturday, with the October sun burning brightly, and the forest of trees in the glen below the cemetery beginning to glow orange and gold, it was a beautiful, peaceful place.  Not as beautiful, though, as Stone Barns, a working farm a short car ride away, which has a delicious cafe and stunning vistas across the local countryside, just an hour outside of Manhattan. Here you can see all sorts of farm animals roaming free; turkeys, chickens, sheep and pigs; as well as their vegetable and fruit growing patches and greenhouses. It was lovely to get away from the hustle and bustle and get some fresh air, and I thought for a moment, as I looked across the rolling green fields, that I was back in England. It was a fabulous day, and has really whet my appetite for more adventures outside of  Manhattan.


  1. how nice that you found somehing this wonderful in your own (new) backyard! I love connecting books and places…and (guilty secret) I love to read menus…so I got great enjoyment from your outing. (And hmmm, my cousins live near Tarrytown, and I haven’t seen them in a while…)

    1. I know – it’s so lovely finding somewhere new that’s so lovely, and being able to make the connection between a book and a place. It has made the legend come so much more alive for me!

      Hahaha! I love to read menus and fantasise about being able to afford expensive dinners involving jus and terrines…one day!

      Go visit those cousins and make them take you to Sleepy Hollow and Stone Barns!

  2. Ooh, what a fantastic post! I think almost everyon can stumble upon interesting things in their backyards but you’ve found something particularly good.

  3. Aha, say I, you know I’ve been waiting for this post now, don’t you? I was so excited to see you had written about it, Rachel, and even more so that you enjoyed your visit to Sleepy Hollow. Reality is often so much more interesting than legend, but, legend is often what brings us to the reality, I think. I certainly understand how this little trip would remind you of your home.

    I love these old cemeteries and their stones with their stories. When we went to Boston, my husband finally put his foot down and said NO! No more cemeteries. I’ve had enough. ha! The stone you have pictured, so sad. Such a young woman and her baby.

    Stone Barns looks like my cup o’ tea. I do believe the Obamas were there in September. It sounds like a wonderful working farm and cafe. Thanks for another good post.

    1. Oh bless you Penny! I’m glad I didn’t disappoint. I know you would have loved Sleepy Hollow – it’s such a peaceful and beautiful place and they really value their heritage.

      I LOVE the cemeteries in Boston and find the inscriptions on old graves endlessly fascinating. A morbid interest, perhaps, but in understanding the dead we can understand the living better!

      You would adore Stone Barns. It’s a gorgeous place. I’m not surprised the Obamas went – there is a Michelin Star restaurant that looked beautiful – sadly it was the much cheaper cafe next door for me!

  4. Ah how wonderful! This looks like just the kind of thing i’d be doing if I were in your position so you are really enabling meto be a vicarious Manhattanite! How fascinating to be able to find out the truth behind the legend and enjoy the fresh air at the same time. I love small towns jn America – you’re reminding me of my brilliant New England/ Canada / New York road trip a couple of summers ago. Which reminds me, if you get the chance to visit the Catskills or Adirondacks whilst you’re there, they too are lovely escapes from the beautiful madness of the city. So much to see and do!

    1. Hahaha! I’m glad, Jane! Small town America is amazing – I can’t wait to see more of it. I did a similar road trip when I was 20 and I have so many happy memories of clapboard houses, American friends and warm and friendly people.

      I am actually going to the Adirondacks for Christmas and I can’t wait! New York state is stunning and I think it’s a shame most people stop at Manhattan!

  5. Ah, yes. I experienced the same letdown the first time I read Sleepy Hollow. In the end, though, I still like the story.

    Thanks for the graveyard picture. I love old cemeteries, and have spent a great deal of time in them lately, trying to find old family members. (Like most American history nerds, I’m becoming entrapped in genealogy. Turns out – I’m British! No shock there!) Our midwestern gravevstones are very different, though. No skulls, and much more polished granite.

    1. Yes, it’s a bit of a disappointment, isn’t it? I wanted more action!

      Old cemeteries are such a lovely and fascinating way to spend an idle afternoon – the artwork on tombstones is very underrated! You have British ancestry? How exciting! You know, I’ve lost count of the amount of Americans who told me that. I think it’s lovely that you are proud of your roots!

  6. Ha! I wondered what you would make of Sleepy Hollow!

    You’ve certainly given us a beautiful picture of a place I for one could only daydream about since I’m unlikely to ever cross the Atlantic. The photographs are lovely too.

    Graveyards are always sad places but the beauty of those old headstones and the peace you found there must have been so good for your soul.

    1. It’s such a lovely part of the world, Chrissy, and I’m glad I could show it to you. New York State is beautiful.

      Yes – I find them quite peaceful and serene places. Remembering that ultimately everything on this earth is temporary always makes me feel better – some people would be depressed by that but not me!

  7. I just read Sleepy Hollow this weekend, so I really enjoyed the virtual trip and historical tidbits! I would love to actually visit the area someday.

  8. When I saw that you worked in Tarrytown I was all set to tell you about Stone Barns. But as I read on I see that you have already been there. The cafe is fantastic, but the next time someone in your work world (with an expense account) wants to take you to a fancy dinner, go to the restaurant there. They don’t offer you any choices they just offer 5 or 8 courses of farm-fresh amazingness. In the summer of 2000 I worked in Manhattan and lived in Nyack, just across the Hudson from Tarrytown. There are two interesting secondhand book stores in Nyack. One is VERY tidy with lots of hardcovers, the other is VERY messy and kind of fun. In Tarrytown, you might also want to go to Kykuit and Lyndhurst. And not that you are looking for more books to add to your list, but The Rose Garden by Maeve Brennan is a collection of linked short stories, many of which take place in that part of Westchester. You might find that interesting given your work location.

    1. Thomas, as ever, you are a mine of useful information! Oh my goodness, I am desperate to go to that restaurant! It looks divine. An expense account is definitely needed though!

      I’m going to have to try and get to Nyack – I like the sound of it very much! One of the frustrations about living here is that I don’t have a car, though, which makes it difficult to get to places that aren’t on train lines. I’ll do my best though!

      More books!? The Rose Garden sounds just perfect – I want to know more about this region. I’ll see if the NYPL has it! Thanks Thomas!

  9. What a wonderful discovery and such a beautiful looking place! It’s so nice that you are able to escape the hubbub of the city sometimes and see different things – it always strikes me as odd when people come to London and don’t visit anywhere else to see some real British life.

    1. Oh Naomi, you would have died and gone to heaven. It was divine! Yes – you know London centric me, but even I have to admit that England’s beauty is overwhelming outside of the M25. Kent, Surrey, Sussex, Yorkshire, Cornwall…I could go on! I love England so much!

  10. Since you liked Legend of Sleepy Hollow, you should look into another short story of Irving’s called The Devil and Tom Walker.

  11. Lovely to see the actual place–I’ve read the story but am planning to read it again this weekend and now I will have visuals. I love the simplicity of the church–thanks for sharing photos.

  12. I just found this post and loved it. I grew up in Sleepy Hollow (back then it was North Tarrytown). Of course we took the place for granted. Only in retrospect do I realize how very special the town is. Thank you for the beautiful pictures.

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