Visiting Ichabod on Eisenhower’s Plane: My Trip to Sleepy Hollow


Unless you work for the Ghostbusters, most of your business trips probably do not involve walking around an old graveyard late at night. But when I learned that business would be taking me to Sleepy Hollow, New York, I knew I would probably spend my free time doing more interesting things than binging shows on Netflix in my hotel room. Visions of Ichabod Crane were filling my head.













I flew into Newark from Dulles on what must be the oldest airplane in United’s entire fleet. I’m reasonably certain that General Eisenhower crossed the English Channel on this plane after D Day. It’s funny how long an hour can feel when you spend the entire hour hoping and praying that the propellers won’t stop working.

After a safe arrival in Newark, I met a colleague who had flown up from Atlanta and we picked up our rental car. We made the drive up past New York City and into the Hudson Valley. I have spent a fair amount of time in NYC, but had never had the pleasure of visiting the Hudson Valley before. It definitely lived up to my expectations of beautiful hills, lush forests and quaint river side towns. It’s easy to see why the wealthy folks of New York view this area as a way to escape from the insanity of the city.

We made our way up to our hotel in Tarrytown, NY. Tarrytown is right next to the village of Sleepy Hollow. We settled in after a nice dinner at a local Greek restaurant in Tarrytown. As the sun was setting over the Hudson Valley I decided to head out in search of the old paths trod by Ichabod Crane.

I made my way to the Sleepy Hollow Cemetery just as the sun was setting. There are a number of famous “residents” of the cemetery. Fittingly, one of them is Washington Irving, the author of “The Legend of Sleepy Hollow”. Unfortunately, I was not able to make my way onto the cemetery grounds, as it had just closed for the night. However, I was able to catch some pretty good views of the cemetery through the gates.

Right next to the cemetery is the Old Dutch Church. Students of history know that New York used to be called new Amsterdam and that the Dutch played a significant role in the settling of New York. This church really earns the title of “Old.” It opened its doors in 1685. Washington Irving mentions it specifically in his story:

“Indeed, certain of the most authentic historians of those parts, who have been careful in collecting and collating the floating facts concerning this spectre, allege that the body of the trooper, having been buried in the church-yard, the ghost rides forth to the scene of battle in nightly quest of his head; and that the rushing speed with which he sometimes passes along the Hollow, like a midnight blast, is owing to his being belated, and in a hurry to get back to the church-yard before daybreak.” —The Legend of Sleepy Hollow

I spent some time walking around the church yard snapping photos. It definitely had a cool, spooky feeling. The only detraction from the spooky mood is the fact that it sits right next to a busy road. I walked around the graveyard looking at headstones that go back many generations and I could not help but wonder what those people would think of what their area has become.

I definitely recommend a trip to this area. It makes for a good break from the hustle and bustle of the City, and I’m sure it is beautiful in the Autumn when the leaves are changing.

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