We took the Metro North train to Tarrytown, and during the ride, I caught a glimpse of the beautiful foliage along the Hudson River, which excited me for the trip ahead. Once we arrived, we strolled along the scenic Riverwalk, which runs alongside the Hudson River and offers a picturesque view of the new Tappan Zee Bridge, which opened in 2017.
I recalled an old college roommate who used to drive across the old bridge with the windows down, just in case it collapsed. LOL. Thankfully, it never did. The bridge was built to last only 50 years due to material shortages during the Korean War. Despite the heavy traffic it handled between Rockland and Westchester counties, it had been deteriorating over the years.
Just a day before our trip, I stumbled upon the Horseman Pumpkin Arch that beautifully frames the iconic Tappan Zee Bridge. It was a pleasant surprise, especially since the algorithm for once worked in my favor! As a huge fan of pumpkin arches, I was excited to capture some photos. Fortunately, the Riverwalk was ideally situated just a short stroll from the train station, making it incredibly easy for us to pop over and soak in the picturesque views.
Taking good photos turned out to be quite a challenge. The sun was blazing overhead, creating harsh light that made it difficult to capture the right angles. To add to the frustration, the ground was unexpectedly muddy despite no significant rainfall in the forecast. I made a concerted effort to navigate the slick patches carefully, trying to keep my boots and skirt as clean as possible.
We took an Uber to Sleepy Hollow Cemetery after finishing our visit to the Riverwalk. Upon arrival, I was surprised to learn we only had an hour to explore because the cemetery closes at 4:30 PM. This oversight was due to my assumption that all cemeteries have similar hours—after all, Green-Wood Cemetery in Brooklyn usually stays open until 6 PM. Oops! Despite our limited time, I made the most of the visit and enjoyed the vibrant foliage throughout the grounds. The colors were simply stunning, and the raining leaves made for a beautiful fall setting!
Fortunately, the Headless Horseman Bridge is only a five-minute walk from the cemetery’s south gate. This rustic wooden bridge has real charm. Sadly, the original bridge that inspired the famous chase between Ichabod Crane and the Headless Horseman in Washington Irving’s “The Legend of Sleepy Hollow” no longer exists. Still, this one has been adopted in its place. A plaque on Highway 9 marks the site of the original bridge.
On our way to the iconic "Welcome to Sleepy Hollow" sign, we took photos with the Headless Horseman statue and the beloved Jack O’ Lantern scarecrow on Beekman Avenue. We wanted to eat at the infamous Horsefeathers restaurant, but unfortunately, it was closed! That was another oversight on my part; I guess they’re not open on Mondays. While it wasn't a must-do for me, it would have been a nice experience. Since no other restaurants caught my interest, we returned to Grand Central and grabbed a Shake Shack meal, enjoying an avocado bacon burger and a creamsicle float.
If I were to do things differently, I would start at the Sleepy Hollow cemetery and make my way down to the Riverwalk, as the sunset would have worked better for the pumpkin arch. Next time, I hope to visit Philipsburg Manor and try Posh Pretzels. One of these years, I will also get to see the Headless Horseman at the Tarrytown parade.
I would love to return to Sleepy Hollow in November if the foliage is still beautiful. Living in Brooklyn makes me miss the greenery and actual landscaping. In my early twenties, I wanted to be a city girl, but now I realize I was mistaken. I need more nature in my life.
With that being said, Happy 150th anniversary to Sleepy Hollow!
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