Halloween Adventures in the Hudson Valley

For the spookiest time of the year, I felt it was fitting to plan a visit to an equally spooky and legendary part of New York - Sleepy Hollow. In that area of the Hudson Valley, I planned to see New York’s beautiful landscape, amazing architecture, and of course, the home of the Headless Horseman the weekend before Halloween. If you enjoy reading, I would suggest reading (or listening to) Washington Irving’s book, The Legend of Sleepy Hollow, before your visit. Ramón and I listened to the audiobook on the drive up (this version which includes spooky music), and it definitely set the scene for what we were about to see.

As an aside, I would like to point out that this blog will discuss what did go to plan and the hiccups that occurred along the way. While some of my blogs focus on the picturesque or a perfect day, I believe that by recounting the fantastical and the trials of this adventure will help some witches, ghosts, and spooked souls to plan accordingly for a Halloween trip to Sleepy Hollow. With that said, let’s begin.

Since Sleepy Hollow is about an hour away from where we live, we headed off the island at about 9:00. Once we were out of the Bronx, the colourful fall foliage and outcroppings of bedrock greeted us to mainland New York. Instead of going straight to Sleepy Hollow, we stopped short of the town and went into Tarrytown to visit the Lyndhurst Mansion. To facilitate visiting the estate, I would either bring cash or buy tickets ahead of time. Also, if you want to explore inside the Gothic Revival mansion, you will need to buy the “Self Guided Tour” ticket (we learned that after we purchased the grounds ticket and had to do some extra walking.)

Lyndhurst Mansion is a unique building in New York, as it was designed in the 19th century by Alexander Jackson Davis to be a Gothic Revival mansion. This is a stark contrast to the mansions found on the Golden Coast of Long Island. As we walked up to the mansion, its grey stone architecture was beautifully juxtaposed by the bright leaves surrounding the building. Once inside, the warm tones of the wood and art collections breathed light into the building. From a staff member inside, we learned that William Paulding, the first owner of the mansion, had desired the place to be made in the Gothic Revival style, even down to the furniture pieces seen within. In the two part library, we were able to see where the original structure ended, and where the extension constructed under George Merritt’s residence began. Yet, the upper floors held more intriguing finds.

In one of the bedrooms on the right hand side, I was caught off guard when I saw a portrait of Anne Boleyn. Maybe the wife of George Merritt loved Anne Boleyn’s story (or loved his wife enough to cause a dramatic shift in the country’s religion)? From another staff member, he explained how after the beheading of Anne Boleyn, most images of her were ordered to be destroyed, a damnatio memoriae of sorts. However, this painting in the Lyndhurst Mansion was done based on an image of Anne from a coin. The point is, portraits of the late Queen were rare and treasured. This context helped explain the consecutive collection in the following hall.

Down the hall, we walked into a spectacular gallery filled to the brim with grand pieces of art, along with an extraordinary stained glass window ahead of us. This almost cathedral gothic style window with plentiful fruit designs was made by, I assumed, Louis Comfort Tiffany. However, after further investigation, while Tiffany worked with Jay Gould on the mansion, some of the windows in this house may have been created by John LaFarge. The mystery surrounding the craftsmanship of different windows in the house did not diminish how astounded I was as I explored the window; some of the vegetation was sculpted as three-dimensional pieces of glass. This helped explain why some plants could look so lifelike and have the light be captured in the same way as a still life. Amazing. I should note that there are many decorated windows in this mansion that are truly exquisite. Yet, this work left me staring in awe for a while.

After a bit of meandering, we headed out of the mansion and down the hill, closer to the Hudson River, to see the Bowling Alley. Yes, the bowling alley is a completely detached building. Out of the mansion, taking a left turn, and then a short descent down the hill, we arrived at the Bowling Pavilion. Inside, I was shocked. Again, we were transported to a different era; wood paneled rooms with a rustic Americana design, made around 1894. Helen Gould had the alley constructed to be the first official standard bowling alley for both men AND women. At one point, I turned around to find Ramón glued to the guide discussing the “pin boys” that were here to reset the bowling pins after each round. I believe he wished he could be a pin boy for a game during our visit.

Eventually, we trodded back up the hill to explore the Carriage House (now the Visitor’s Centre), along with the Gothic Fair that was taking place. Though, with the day moving along faster than we would have liked, we knew we should head into Sleepy Hollow sooner than later.

As we drove from Tarrytown to Sleepy Hollow, I saw that there would be a Halloween parade from 14:00-17:00. Perhaps a blessing in disguise for us, the place I was planning for us to eat at had an extremely long line, which happened to also be on the parade route. To ensure that we would not be stuck for an eternity nor go hungry, we chose a cute Greek restaurant nearby for lunch (and found different parking). After a relaxing meal, we walked off the calories and stopped into the Sleepy Hollow Bookshop. For those looking for some fantasy or spooky books, I recommend stopping in. Staff members also have a free stamp they can put in your book showing you visited Sleepy Hollow.

Now, if we thought the parade would be our only hiccup, we were wrong. With the time remaining, our goal was to visit Kykuit, the Rockefeller Estate (or what I thought was the Rockefeller Estate), the Headless Horseman Bridge, and the Old Dutch Church. Parking was overflowing at the Visitor’s Centre, so we were sent to overflow parking. Which, to be honest, included a beautiful autumn walk to the ticketing building. Yet, once at the Visitor’s Center, we learned a few things. First, tickets can be bought here to visit and tour Kykuit, but the estate was actually a seven minute drive away. Secondly, even if we wanted to visit, all the tours were gone and booked. Same for the Philipsburg Manor across the pond from where we were standing. Note to self, book in advance if I want to visit around Halloween again.

I would like to say that there were no other speed bumps the rest of the day after this, but I would be lying. However, we kept the mood positive as the day started on a high note. Also, I knew at the start of the day that we can always return next Halloween.

As we walked away from the Visitor’s Centre towards the Old Dutch Church, we saw the Headless Horseman Sculpture to our right, and soon after the Headless Horseman Bridge to our left. In addition, one of the houses across from the church was apparently the house of the former Gatekeeper of Sleepy Hollow. While the church and graveyard were unfortunately closing up by the time we arrived at its gates, we were able to at least get a sneak peek of the area for next time.

As we walked back to the car, we took some time to enjoy the fall foliage and views of the Philipsburg Manor. Eerie music was playing in the distance - most likely for the evening events - and slowly ushering us to our car. Little did we know, something spookier was about to happen… traffic.

The traffic we experienced was not just any traffic, but the holiday, small town traffic where the main road and some side roads were closed down for the town’s Halloween block party. In a way, it felt almost apocalyptic as I wondered, will we ever escape? On the bright side, we were able to see all the creative costumes people wore to this event. I would say the most popular costumes were clowns, witches, and dinosaurs.

Regardless of the twists and turns of the day, it was still an amazing day in Tarrytown and Sleepy Hollow. With the orange street signs, the Headless Horseman plastered all over school buildings, and every house decked out with Halloween spirit, I could tell that this town lives for this season and its literary history. If I were to explain this trip as a long story made short, I would describe the adventure as a taste of all that we could see here, with more unknowns to explore for next time.

In order for future visits to be less hectic, I would recommend a few housekeeping items:

• If you are not a fan of crowds, I would avoid visiting in October.
• For major landmarks in town, get to Sleepy Hollow early and book tickets ahead where applicable.
• Take note of any events and their locations that are happening in this area during your intended visit.

In the meantime, I look forward to our next visit up to Sleepy Hollow, and the surrounding Hudson Valley area, to discover more hidden treasures.

Thanks for reading, and until next time.

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For any questions you may have about this adventure, head over to my Instagram or Buy Me a Coffee page to share your inquiry. I will respond to these questions in the next blog.

Also, if you are interested in any art related to this blog, head over to my Etsy page where I have shared a watercolour inspired by our visit to the Lyndhurst Mansion.