Despite its young age, the United States is full of haunted history. And fans of the paranormal love to immerse themselves in the lore of these locations, myself included.
One landmark on my spooky bucket list has always been Sleepy Hollow. Though based on a work of fiction, I’ve always found it captivating that an author like Washington Irving simply took his surroundings and built a supernatural ghost story around that setting, populating it with real people and letting his imagination run wild to become the stuff of literal legend.
And in the spring of 2023, I was lucky enough to make my pilgrimage to the quiet little town. Below is my day trip to Sleepy Hollow.
Traveling to Sleepy Hollow
My sister and I took the train from New York City to Tarrytown via Grand Central Terminal. It was the first Wednesday in May. And while we didn’t have that rich fall foliage to really set the mood, the day was cold and gray with periods of sunshine which set a nice balance of a spooky atmosphere with ideal travel conditions.
We caught the train at 10:20 am, waiting until after peak hours when the ticket rates fell. And at our scheduled time, we made our way to our platform to the open train. We purchased our tickets at a machine. So, we were a little confused as to when to hand them over. As we boarded, the conductor stood there preoccupied with something else, and everyone else just boarded without showing or scanning a ticket.
Once we were underway, I thought about old movies that I’d watched where conductors walk from train car to train car and punch the tickets of the riders as we go. Sure enough, a few minutes into our trip, someone did come around asking for our tickets which we handed over and were then punched.
We took the Metro-North through the Bronx and Harlem, stopping every so often, just like the subway. Eventually, the urban scenery turned rural as the Hudson River came into view on our left and thick, green trees were our only view to the right.
Arriving in Tarrytown
We exited our train at the Tarrytown station and found ourselves in a parking lot full of cars but no people. Ahead of us was a steep, curved hill which, according to our map, we needed to climb.
As we ascended into Tarrytown, we passed by standard suburban homes. They didn’t look historical or nostalgic in any way, just comfortable, lived-in houses that wrapped around this hilly town, similar to our own hometown.
As we continued to climb, the homes turned to small businesses, including the music hall which reminded me of a tiny Radio City Music Hall with its neon lighting outstretched over the metal awning of an old, red brick building. The road was under construction, and the sound of jackhammering reverberated down the street.
First stops in Tarrytown
At the top of the hill, we stopped at a 7-Eleven on the corner for a cold drink before proceeding to the end of the road to a pair of churches. One, a red brick church called Christ Church, contained a plaque describing this as Washington Irving’s church. Behind the sign was a patch of ivy-covered wall which the sign explained was constructed from clippings taken from Irving’s home in Sunnyside.
We made a U-turn and continued down the other end of the street, passing by more homes. It was quiet. Occasionally, you’d see someone working on a car or gardening. But it seemed that most people were at work. And since it wasn’t their peak tourist season, and tours at this time of year only take place on the weekends, we were literally the only two tourists visiting that day.
At one intersection, we came across The Landmark Condominium, a wide, red brick building that served as inspiration for the Van Tassel mansion in The Legend of Sleepy Hollow.
The front yard contains a statue in honor of the locals who served in World War I. The building itself is in good shape but doesn’t give off a particularly creepy vibe. It feels more like an old school or a public building.
The front of the building is filled with windows of all shapes and sizes, and the yard is neatly landscaped. Tulips were planted along the wall that boarders the sidewalk, and giant trees stood tall in the grassy yard.
We passed by Bella’s Boutique and, intending to buy our souvenirs there, we came to find that the store was opening an hour late that day. So, we headed down the street and came across Warner Library. There, we stopped to use the bathroom.
Though it has an older look to it, the library was updated inside and felt like any local library I would visit at home. Old men sat in cushioned chairs reading the newspaper while other patrons were typing away at the computers. From one of the rear windows, I could see the river and the Governor Mario M. Cuomo Bridge in the distance.
Shopping and dining in Tarrytown
By then, it was noon. So, we backtracked to Bella’s Boutique which was now open. The front door was open, and masks and hand sanitizer were placed next to a sign in the entryway, though there was no requirement to wear one or sanitize before entering. It’s just one of those lasting effects of Covid that I think is here to stay.
The shop had a nice variety of gifts with about half of the store devoted to The Legend of Sleepy Hollow merchandise. I bought a long-sleeved shirt with the headless horseman rearing his horse in one of the upper corners. I also bought a magnet featuring The Old Dutch Church.
A lot of the Sleepy Hollow merchandise was made by local artists. So, it felt good to be supporting independent creators rather than the junky souvenirs that you usually find on vacation.
We then crossed the street to a restaurant called Horsefeathers. This restaurant is prominently featured online, and I was afraid that it would be hard to get into. But because it was a weekday and just opening, we had no trouble getting in.
The outside seems pretty modern and is connected to a few other stores in a long building with tables set up in the front over a blue awning.
We decided to eat inside which had a tavern-style design with wood paneled walls and tables. We ordered lunch which was served on metal plates. Our waitress was friendly, the service was fast, and the food was good.
Patriot’s Park and a parade
After lunch, we continued down Broadway and approached a sign reading “Village of Sleepy Hollow.” A long line of children were pressed up against the fence looking at the street. I assumed they were school children at recess, but I also thought it was strange that they were all just staring at the road instead of playing in the playground or the grassy hill behind them.
On the other side of the street was Patriot’s Park. Again, it pays tribute to the town’s Revolutionary War heroes, something that feels as important to the town’s history as the famous horror story.
There, we walked around a stone set of stairs and three bridges that surrounded a brook complete with mini waterfalls down below. A few mothers were out pushing their young children in strollers, and a few police cars were parked at the edge of the park facing the road. I noticed that the logo on their doors featured The Headless Horseman which made me so happy.
As we emerged from the park back on the road, a parade of police vehicles drove past with their lights flashing and sirens wailing. The children behind the fence cheered and rang cowbells as they passed, and I realized that this is what they had been waiting for. Towards the end of the procession, a group of joggers passed by, two of them holding unlit torches and carrying flags for the Special Olympics.
After the parade had passed, we continued on our way. We passed a stone Catholic church nearby with a plaque reading that the church was dedicate to Washington Irving, as most things are there.
Entering Sleepy Hollow
On the opposite corner of the street, we spotted the famous “Welcome to Historic Sleepy Hollow” sign and proceeded into this section of town. Empty recycling cans were lined up on the sidewalk of the neighboring homes, and again, I was delighted to find that The Headless Horseman is prominently featured as the town’s logo. I was told that a local woman looked at me funny as I took a photo of one of the bins.
On this stretch of road, I started to see some more interesting homes with octagon-shaped spires, wide front porches, and intricately painted trims. But most of the homes were simple brick or wood frame structures that looked unassuming and lived in.
This is a fully functional, idyllic town that just happens to be the setting of a famous story. We saw signs for upcoming children’s programs and other local events. They work around the historical stuff, leaving it intact while building a real life around it.
When we reached Phillipsburg Manor, its parking lot just appeared in the middle of this suburban landscape. The manor was closed that day, but we walked up to the fence and snapped a few pictures of the house and mill overlooking the pond. The sky had grown overcast at the time, forming that perfect eerie lighting that reflected off of the water and made the surrounding pastel colors of spring pop.
The Sleepy Hollow Bridge
As we walked further downhill on Broadway, we reached the Sleepy Hollow Bridge, the one from the story. It wasn’t that red, covered bridge that you know from the movies and never had been. It’s just a simple concrete bridge that overlooks the Pocantico River which narrows into a small creek in this area.
There’s a stone railing on one side of the bridge and a wide sidewalk that makes it safe to cross on foot while vehicles pass by on the road. There’s a lot of vehicle traffic, and it doesn’t really have the allure of the story. However, it does lead to the Old Dutch Reformed Church and Cemetery, a small, stone church that sits sideways on the hill.
The Old Dutch Church and cemetery
We entered the cemetery through the tall, open iron gates, passing by a sign warning that the cemetery closes at 4:30 pm. We pondered what would happen if we left the cemetery at 4:31 pm. Would we be able to get out?
Not far from the entrance is a narrow concrete path leading into the cemetery. The ground is packed tightly with gravestones of all shapes and sizes, many of which look ancient, particularly the graves that surround the church.
We first followed the path towards the church. A blue shed on the edge of the property near the driveway contains several pairs of wooden shoes nailed to the wall. I later looked up the meaning of the shoes being nailed to the shed and found that it’s simply a tribute to the church’s Dutch heritage.
Several flowering trees are located in the churchyard. Thanks to some YouTube research, we had no trouble finding the grave of Eleanor Van Tassel, the inspiration for Katrina in the story. The Van Tassel family is spread throughout the cemetery, but she’s located in the front of the churchyard and is one of the taller, more eye catching stones in that part of the cemetery.
We also had no trouble locating Washington Irving’s grave. He and his family are buried in an enclosed plot of land complete with a set of stairs and a low, gated metal fence. We paid our respects standing at the top of a set of concrete steps on the outside of the gate.
The cemetery seems small at first, and I didn’t expect to be there long. But as the path continued uphill, we encountered section after section filled with graves.
Ancient mausoleums lined the path heading upwards. These buildings were constructed of ivy-covered stone with creepy-looking doors, some of which were secured with locks. I wondered if these locks were meant to keep people out or keep whatever was inside in. The glass of one of the doors was broken, and I peeked inside to reveal that it was completely empty inside.
At one point, my sister was startled by a deer. Deer are nothing new to us, and this one was minding its business, but it was also wearing a brown collar, and its ears were tagged.
We continued around the path, seeing impressive buildings, statues, and other grave markers for seemingly important people. A canon was positioned at the top of one hill overlooking the trees.
We continued to follow the winding path which led us deeper into the cemetery at this vast landscape of tall, thin graves. I kept an eye out for Andrew Carnegie’s grave and even pulled up a photo of it, hoping that the surrounding landmarks would help me spot it, but I never did.
The wooden bridge in the woods
Finally, the path curved downwards, and over the hill, I could see the wooden bridge which is named “Old Style Horseman Bridge” on Google maps. It has a spookier feel that’s more like a scene from Irving’s story, but it’s still not a covered bridge.
The bridge is drivable and leads over another part of the Pocantico River which was still very shallow, though the water rushed more aggressively under the bridge. It leads up to a long walking trail.
We stopped to rest at the bridge and take in the setting. Here, I busted out a famous New York black and white cookie that I had purchased at a bakery in Grand Central Terminal early that morning.
We then followed the road down, hoping that it would lead us back to a main road and found that it led us exactly back to the entrance of the cemetery. We exited and down the road, we came across the metal statue of Ichabod and The Headless Horseman on a patch of green.
Suburban Sleepy Hollow
From the statue, we continued through the town, walking past more homes and shops. By then, the kids at Sleepy Hollow High School were dismissed for the day, and we walked home with many of them as they ran down the street with their friends.
We also passed a children’s bookstore which was a tiny little shop filled with classic picture books. By then, I was running out of steam from all of the miles we had logged and had yet to cover. My step count by the end of the day between Sleepy Hollow and New York City totaled 14 miles.
Tarrytown Riverwalk
At the end of the road, we again reached the Hudson and the start of a path known as the River Walk Park. We walked out to the pier overlooking the river and got a closeup view of the Cuomo Bridge that I had seen at the library earlier that day.
There is a lighthouse along the river, but it was under construction at the time as was the road that leads to it. So, we didn’t get very close to it.
We followed the river downward and ended up back at the train station. There, I found a bathroom, and afterward, we weighed our options.
Do we hike the two miles to Sunnyside, The Octagon House, and Lyndhurst Mansion? None of these buildings were open for tours that day. So, we’d only be seeing the outsides of them. From there, we could take another train station back to New York City, but we would have to pay up since it would be back to peak hours by then.
We elected to take the 3:58 pm train back and save some money on our ticket. I’m always worried that if I don’t see everything at a new place the first time, that I’ll never get the chance to come back. The town is small, but its attractions are spread out. My exhaustion outweighed my tenacity. And as a result, I know I’ll have to come back some day, preferably later in the calendar year when the tours are running regularly and everything is open.
Final thoughts on Sleepy Hollow
As much as I love to travel, I can’t see myself living anywhere other than my hometown. Sleepy Hollow is the one place I’ve been where I found myself thinking that I could live there. It felt like home to me with that added allure of being a historical site, not only in a literary sense, which is why I came, but also as a prominent place in American history, particularly our early history.
The lack of spookiness on that quiet spring day did not deter me from finding the charm and excitement in that town. Instead, it made me appreciate it for its realism rather than its legendary status. And don’t we all want to be appreciated for our most authentic selves?
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