Sleepy Hollow: Journey Into a Fairytale

To me, love of travel and love of literature really go hand in hand. Reading about something instantly makes me want to experience it. Of course this isn’t always so easy and sometimes visiting a place I read about just has to go on the bucket list. Luckily for me, this was not the case with the mystical village from Washington Irving’s short story “The Legend of Sleepy Hollow”.The idea of visiting this town arose from conversing with a friend – he talked about an interesting day trip he and his wife took to a town called Sleepy Hollow, only 40 minutes away from my hometown. My literature-loving ear was immediately intrigued. Could it be that Washington Irving’s tale took place just a short drive away from where I live? Apparently yes. Sleepy Hollow turned out to be a small town on the Hudson, neighboring the larger Tarrytown.


I traveled to Sleepy Hollow with my friend Nathan, and both of us studied up for our trip by reading “The Legend of Sleepy Hollow”. This short story (approximately 40 pages in length) is about a superstitious schoolteacher named Ichabod Crane, who competes with the macho Brom Bones for the hand of coquettish Katrina Van Tassel. Katrina is the only daughter (and heir) of a wealthy farmer, and Ichabod hopes that marriage to her will advance his social standing in the community. One spooky evening though, Ichabod finds himself violently chased by “the headless horseman”, the ghost of a beheaded Hessian soldier, who is purported to haunt Sleepy Hollow. Ichabod disappears and all that’s found of him are some articles of clothing and a shattered pumpkin. Though the townspeople chalk what happened up to spirited intervention, Washington Irving pretty clearly implies that Brom Bones was “the horseman” and that the shattered pumpkin was the head that the horseman hurled at Ichabod to unseat him. The story is ripe with vivid language (particularly describing the placid demeanor of Sleepy Hollow), powerful observations on the nature of the human condition, and pointed social commentary. And though it may be located in the children’s section of your library, due to the archaic flowery language Washington employs, it is by no means an easy read.

Nathan and I set out on our trip at 8 am on the 14th of September, a Sunday. Rather than going straight to Sleepy Hollow, we started out day by going to the Irvington Farmer’s Market. The market was cute albeit tiny, with lots of homemade food samples and cute doggies trotting around. We had delicious light breakfast at the market, mostly by going around from stand to stand and trying samples.

With full bellies, we then set out to retrace the iconic places mentioned within “The Legend of Sleepy Hollow”. Mostly we wanted to follow the path that Ichabod rode on as he was being chased by the headless horseman. Therefore we drove to Patriot’s Park, where a memorial commemorates the foiled betrayal of Major John André, who was discovered colluding with Benedict Arnold and was hanged for his treachery. In the short story, André‘s ghost haunts the area and here Ichabod first sees the headless horseman. Additionally, the creek constantly mentioned in the text runs through this park. In terms of touring, there isn’t really much to do in Patriot’s Park. We took some scenic photos of the monument and the creek and were promptly on our way.

Next stop on the trip was The Old Dutch Church of Sleepy Hollow and the Headless Horseman Bridge. This is one of the oldest churches in New England and has an ancient adjoining cemetery. Within the legend, Ichabod desperately races to a bridge to cross the creek to ride into the church, because folklore dictates that spirits cannot enter the holy territory of a church. This doesn’t work out too well for Ichabod though since the headless horseman crosses the churchyard just fine and unseats him with the pumpkin on this bridge. The bridge that leads to the churchyard now obviously isn’t the original rickety wooden bridge of the story. Instead it’s an imposing but very picturesque stone structure. Even though there is fancy plaque on this stone bridge stating that it is located where the original bridge used to be, this is blatantly false. The location of the original bridge was about 0.3 miles upstream.

The church itself, built in 1685, has a very historical vibe to it. Looking at it really transports you into the Sleepy Hollow Irving described. In the adjoining Old Dutch Church Cemetery we found the graves Eleanor and Katrina Van Tassel. Though Irving’s character has the name Katrina she was actually was based off of Eleanor Van Tassel, who was friends with the author as a child.

Ichabod rode from Patriot’s Park, down the street in Sleepy Hollow now called U.S. Route 9, all the way to the creek and then crossed the bridge leading to the Old Dutch Church. It’s hard to imagine that this route was covered with forests at one point as it is such a quaint and bustling little village now.

Road down which Ichabod rode. Back then it was covered with forest.

At this point, we had ended retracing Ichabod’s steps and took a fascinating walking tour, called “The Original Knickerbocker Tour”. This tour took us through the Sleepy Hollow Cemetery (not to be confused with the 2.5 acre Old Dutch Church cemetery which adjoins but is not part of it). The tour references Knickerbocker because “The Legend of Sleepy Hollow”, published originally in The Sketchbook of Geoffrey Crayon is supposedly narrated based on the notes of someone named Diedrich Knickerbocker. Both Geoffrey Crayon and Diedrich Knickerbocker were pseudonyms of Washington Irving. Apparently, Irving was a famous author even during his lifetime, so famous in fact that the basketball team the New York Knicks was originally the New York Knickerbockers, named after this pseudonym of Irving.

The walking tour, which lasted about an hour, took us to the Irving family burial plot. Irving’s tombstone had to be replaced twice because his fans kept cracking pieces off it for good luck. The tour guide then led us through other notable monuments in the cemetery from the Victorian era: a revolutionary war memorial, the gothic revival monument of a New York City dry goods merchant, a marble monument created by Augustus Saint Gaudens (sculptor of the golden “Diana” with a bow from the Metropolitan Museum of Art). John D. Rockefeller and Andrew Carnegie are also buried at the Sleepy Hollow cemetery but we didn’t get a chance to see their monuments (Nathan being a Carnegie-Mellon student was very upset about missing that last one).

We ate lunch at the Bridge View Tavern, which serves delicious burgers and has breathtaking views of the Hudson and the Sleepy Hollow lighthouse. After lunch, we took a two hour tour of Kykuit, the magnificent Rockefeller family estate right near Sleepy Hollow. The estate overlooks the Hudson and the New York City skyline and is almost 250 acres. Four generations of Rockefellers lived in there and two-thirds of it was donated to the National Trust for Historic Preservation. The last surviving Rockefeller lives on the remaining third. John D. Rockefeller Jr. was the contractor for the estate since, as he wasn’t much of a businessman, his father John D. Rockefeller Sr. (the founder of Standard Oil) gave Kykuit to him as a pet project. He became such a good contractor went on to construct many other notable buildings of the Rockefeller legacy.

The estate consists of a six-story stone house, lovely gardens and a coach barn. Symmetry was essential to the estate’s architecture. The house and gardens showcase magnificent art collections, particularly pieces of modern art loved by New York Governor Nelson Rockefeller. Works by Pablo Picasso, Andrew Warhol, Marc Chagall, Henry Moore, Alexander Calder, Louise Nevelson, and David Smith are all exhibited. The gardens of Kykuit were designed by architects William Bosworth and Frederick Law Olmstead (who designed Central Park). They were specifically planned to showcase the modern sculptures of Governor Rockefeller’s collection. The tour was very informative – we learned a lot about the devoutly Baptist Rockefeller family and their history and way of life. It’s pretty crazy to think that these people could go and chill in a basement with their personal world-renowned art collection.

Our last stop was the Union Church of Pocantico Hills. This is a gem housing stained glassed windows by Henri Matisse and Marc Chagall, which were commissioned by the Rockefellers. The Rockefellers begged Matisse, who at that point was a sick old man, to create a design for the stained glassed window above the altar. Matisse was terribly sick at the time and did not want the commission. Yet after Abigail Aldrich Rockefeller (John D. Rockefeller Jr.’s wife) who had been Matisse’s close friend passed away, he agreed to do this window as a memorial to her. Matisse died two days after finishing the paper cutouts of this window and the actual stained glass was manufactured by his daughter after his death. The Chagall windows were commissioned by his brother David Rockefeller, to memorialize Rockefeller Jr. after his death. David saw Chagall’s windows from the Hadassah medical center in Jerusalem and asked the artist to create a stained glass window of one of the great philanthropist’s favorite bible passages, The Good Samaritan. Later Chagall created 8 more windows of biblical scenes featuring prophets from the Old Testament, which memorialize members of the Rockefeller family. The church really is magical with its romantic neo-gothic architecture and its tiny, cozy interior. Chagall’s expressive and colorful stained glass windows come to life and highlight the lovely Matisse in the center. Photos are not allowed inside the church, but feel free to google to find out what the windows look like.

Unfortunately Nathan and I didn’t have time to visit Lyndhurst (a gothic revival mansion) and Sunnyside (Washington Irving’s estate) which are also in the area, but we are definitely planning to go again. If you live in the vicinity or are passing by Sleepy Hollow/ Tarrytown, I would highly recommend not just one but multiple visits. Of course start by doing your research: read “The Legend of Sleepy Hollow” and check out for additional information about the sights there. You will be enchanted by the lovely, fairytale village, its rich history, and the incredible estates that it houses. Make sure you give yourself time to walk around and soak it all in.

Thanks for reading. All photos in the post are originals. Feel free to comment or reach out to me with any questions. Till next time!


2 thoughts on “Sleepy Hollow: Journey Into a Fairytale

  1. Sounds like a really fun trip! There are so many cool places to explore near us! Also, this piece was really nicely written 🙂 can’t wait to hear where you go next (and hopefully not just with Nathan, lol).

    Liked by 1 person

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