Sleepy Hollow – A Pleasing Haunt for Both the Living and the Dead

A Real Life Halloween Town.

As a 90’s kid (only 90’s kids will remember, only 90’s kids can do anything of value or significance, only 90’s kids are real humans and everyone else is a robot) I religiously watched all of the Halloween cult classics, namely Hocus Pocus, Nightmare Before Christmas and Halloween Town. I have fond memories of re-creating my very own cinema inspired Halloween Town in my parents’ basement with my cousins every October. I also have memories of asking my mom what a virgin was after watching Hocus Pocus, but that’s a tale for therapy, not here. As children, we were always enthralled with the idea of there being an otherworldly place entirely devoted to Halloween – full of monsters, skeletons, orange and yellow leaves hanging off of the trees, vampires, candy, and pumpkins for miles most importantly having a list travel destination for Halloween in New York .

The search for a real life Halloween town had become diminished significantly over the years, what with being an adult and all, but not completely dissipated. I always found myself looking forward to the new autumn season. It was a promise of new beginnings and adventures as well as the “breaking out“ of the cozy clothes wardrobe. A shift in priorities as a now married individual had resulted in a focus heavier on national travel as opposed to international travel for me. This disappointed me slightly because travel, is and was, how I restore my sanity, plainly put.

Travel is how I fix the broken pieces of myself that I often did not realize needed healing until I arrive at my destination. Eliminating travel altogether would never be an option for me, so I considered how to create travel experiences within my means, thus, a visit to Sleepy Hollow NY, New York for the Halloween season was in order.

Short of ghouls, goblins, and getting away from the papers desperately needing grading, I was not sure what to expect, or what I would find. At best, I figured I would get two full days of alone time with my husband, which is rare as we both work full time in demanding professions. I certainly never thought driving an hour past my home would serve any kind of meditative or anxiety easing purpose. The irony I experienced in Sleepy Hollow, during its signature Halloween season was indeed unexpected.

In a place that is so laden with skeletons, tombstones, as well as other motifs of death and decay, I felt incredibly alive and able to breathe for the first time in weeks.

The Quickest Road Trip Ever.

The noise and light pollution of New York city gradually faded into the palate of navy blue and gray sky behind us as we drove the one and a half hours (traffic, you know?) to Sleepy Hollow on Friday evening. What strikes one instantly upon arrival, is how far away it feels despite being SO close to the city. A back to nature experience is not something you need to go searching for in this part of New York, it permeates the entire area. On our drive to just about everywhere in the town, we passed lakes, trees performing their most popular act – the changing of the leaves, and woods which seemed to stretch on endlessly.

We stayed at a local Days Inn to save money, which was just fine, but definitely would not have surprised me in the least if an ax murderer showed up at our window one night to do his thing. The rooms and buildings were disconnected and not within a single building, that is to say, you had to step outside to get from one room to the next. It was in a small, quiet, area and as my husband stated, “This is nice, but I prefer hotels where everything is safely inside a building.” The feeling of being in an unfamiliar and remote location combined with the now blackened sky curtaining around us left us wondering if this were all part of the “spooky” experience. We did a quick unpacking of our belongings, and we were off on our 48 hours adventure.

Sleepy Hollow Cemetery (Classic Evening Lantern Tours).

A tour of the cemetery by LANTERN LIGHT! This was a truly unique, spooky, and informative event which damn near FORCED us to be in the spirit for Halloween. The stories and history about the people buried in the tombs – particularly one about a missing arm- that our group stopped at along the way were fascinating and highly entertaining. Such famous people as some Rockerfellers, Andrew Carnegie, and Washington Irving himself are buried at the Sleepy Hollow cemetery.

We also visited the cemetery in the afternoon the next day and found it to be tranquil and beautiful, I have already declared to my husband and parents proudly and loudly that I would like to be buried there some day to which are SO many opinions. Namely, “who the hell is going to visit you up there?” from my father, Steven Soprano. The cemetery’s purpose was and is to function as both a place of relaxation for visiting families as well as an outdoor art exhibit which is why perhaps it is so popular. It is more awe-inspiring than it is a reminder of dying.

Irving’s Legend – Old Dutch Church. 

Without a single doubt, the highlight of our trip. Here, you get to visit the original Dutch Church where Washington Irving’s Legend of Sleepy Hollow takes place. Without the use of fancy movie equipment, the story teller does a ridiculously good job of engaging his audience in the thrilling tale, leaving each guest on the edge of their seat as well as doubled over in laughter several times.

As a teacher, I could only aspire to be half as entertaining. The howling wind rustles the windows and squeaky floors of the original 1600’s Dutch church as the story teller performs nothing short of real life magic for all to see. I was contented to see that not a single phone was taken out, not a whisper uttered from one guest to another, that with his pure talent, he was able to capture the heart and full attention of all in the room for the duration of his performance. Book early because these performances fill up fast!

The graveyard behind the Old Dutch Church is a slice of American history, with some tombstones dating all the way back to the Revolutionary War (these are marked with a placard and an American flag.) Of course, there are homemade treats to be purchased (cider, beer, donuts, candy) while you stroll around. Try all of them and have no regrets about doing so.

Fare Finds.

We encountered several impromptu markets, fares (including a psychic fare!), and drives while we explored for the weekend. Spoiler alert, I didn’t go to the psychic fair because it would horrify my Italian-Catholic mother…womp. However, we did find an awesome scene happening at the Union Church where we purchased over 20 books in brand new condition for a mere 20 dollars! In keeping with the spooky spirit, my husband reminded me that these were a steal considering I often will pay $70 for a mere five books at Barnes and Noble. The realization left me turned white, as if I had seen a ghost…the ghost of remembrance of my last credit card statement.

The Un-Silent Picture.

A crowd of people fill into a giant tent in front of a projector screen where a live band sits to the left, and a skilled sound magician sits to the right. The black and white film begins and is about an hour long. It is completely silent, and the sound technician and band provide sound effects and music to correspond perfectly to the events happening with the movie. I had never seen a silent film before and my experience felt like a trip back in time to a period I often obsess over, the 1920’s. The film was eerie in some respects, yet light-hearted in others, with more moments of laughter than suspense. The acting was superb and I feel that this event is far underrated.

Sunnyside – Washington Irving’s Estate.

 I am unashamedly a literary and historical nerd. As such, I was very content that we were able to spend some time at Washington Irving’s former estate, Sunnyside. It is an idyllic and picturesque home situated right on the Hudson River. The staff are all dressed in period clothing and created a whole-hearted immersive experience explaining his life and inspiration for his work with enthusiasm.

While it seems small from the outside, the home inside was cozy, impressive, and felt as though it had been perfectly preserved. You are not allowed to walk about freely, at each room a costumed host tells you of how Irving would have lived and what he enjoyed doing in each location of the house. I was admittedly not aware of just how much of a literary giant that Irving was until I visited.

His Sunnyside estate was a featured painting in nearly every American home of the 1800s. Irving knew Romantic big wigs such as Mary Shelley (who pursued him as a love interest!) and Charles Dickens, who actually came to visit the home. As the story goes, Dickens was so fond of Irving’s 93 year old relative, Ebeneezer, that he may well have been Dickens’ inspiration for creating A Christmas Carol.

I was floored that such an important literary site was so close to my home. Irving and his work are renowned around the world and his legendary work featuring the headless horseman has permeated every form of media both nationally and internationally. Sunnyside is a true treasure which takes you back in time and makes learning about this American legend’s life rousing . Highly recommend!

Quality Food.

Breakfast, ashamedly, was not something we partook in during any of our days in Sleepy Hollow. However, these places…THESE places…could stand tall against anywhere in the Big Apple!

Pik Nik.

If you want to weigh your options of where to eat, then don’t even come in here looking for a menu to “browse.” Once you smell what’s cooking at this retro BBQ joint, you won’t leave. It is a “come to the counter” ordering system which allows you to see many of the sides offered on display before you choose them. We ordered the pulled pork, potato salad, kale salad to put on the appearance of being healthy, and mac and cheese. If you go somewhere, and the side option includes mac and cheese, then that is what you pick, or else you’re an objectively awful human.

The atmosphere does a fantastic job of making you feel as though you’ve wandered off the back woods of a southern road trip into some small feckless, yet charming town with banging food. The wait for your food is average, enough time that you know its actually being cooked with a personal touch, and not so long that you’re gnawing your arm off as an impromptu appetizer. Pay attention to the music and jam out as you wait, it’s an impossibly impressive mix of classic rock and roll. As expected, the mac and cheese, as well as all of its friends accompanying it were delicious and left us full enough to hate ourselves, which earns my applause. A job well done, unique, and highly recommended to all.

Horsefeathers.

A classic. Horsefeathers is the popular girl in town and rightly deserves the title. It’s a cozy, dimly lit tavern style eatery (which really puts one in the fall/Halloween spirit) with delightful staff, lively guests, and a dizzying array of mainly comfort food options. Having visited Rockerfeller’s grave earlier, I was inspired, and so splurged and ordered the Alaskan king crab legs with drawn butter which, I admit, I still dream about one week later. (Don’t judge me until you’re ready to share what YOU dream about.)

My husband, the half of us with self control, ordered a healthy, California style burger with avocado and all the green things. The beers were pouring, the chatter was loud and the laughter even louder. It’s an exceptional place for a date, with friends, or for a family. I don’t feel that my words nearly do it justice, and I was too shy to take a photo because it was PACKED, but something about sitting in low lighting, eating feel good food with warm faces all around felt so…right. It was a good reminder that I was indeed, despite being an hour away, NOT home anymore, and that I should let my hair down and enjoy the “all are welcome” attitude and merriment. Horsefeathers is a great way to start a weekend in Sleepy Hollow, it will get you into the spirit almost immediately.

Guadalajara.

KNOCK OUT Mexican food and atmosphere. The wall near the bar is full of famous people…although…it’s actually unclear to me if these celebs have actually eaten there, or if the staff just put their photos up because they like these people. BUT, if those framed faced HAVE NOT eaten here, they’re wrong. The food is fresh, rich, and you for sure get your bang for your buck as far as portions go.

The guacamole and fried ice cream are made table side, the margaritas are giant/will knock you on your ass, and the queso fundido is absolutely my last meal if I ever wind up on death row. I would drive from Brooklyn, to Sleepy Hollow, JUST for that dish alone. The staff is quick on their feet, pleasant, and the restaurant itself is warm, spacious, and inviting. There is outdoor seating in the front for when the weather is nice. I tried finding a website with a menu online, but it evidently doesn’t exist? Just live a little and go without cross examining the menu beforehand. You won’t regret it.

A Much Needed Mini Get-Away.

Traveling is not about getting the farthest away. A lot of times, it’s more about going closer, closer to your own self than you have ever been. The pace of life in Sleepy Hollow was relaxed, the stars iridescent at night, and the world more spacious. Before this trip, I had been working myself ragged. On top of this, I had recently found out I was pregnant. I had been staying up at night to complete assignments, working on weekends, and falling asleep to and waking up to full blown panic attacks which I hadn’t experienced in several months prior.

I’m not one of those people who wants to run out on New York and “quit my 9-5 to go remote.” I like working hard and long hours in the city that never sleeps, not many people have that opportunity. I’m deeply satisfied to have a foot long to-do list and to check the items off one by one. I get a high from that feeling of being bone tired, and peeling oneself out of bed at 5 a.m. after falling into bed at 12 a.m. and subsisting on coffee after coffee. Sometimes, as was the case before this trip, I don’t even realize how much damage I do to myself when I get into a cycle of work, sleep, packed out weekend with events and extra work, repeat.

Like a hamster on a wheel, I keep going and going running myself in circles until the next break from teaching. When I arrived in Sleepy Hollow and really took in the vastness, I remember feeling my shoulders soften for the first time in weeks. My constantly congested head felt as if someone gently put a pin in it and released all of the racing thoughts and massive tension within it. For two days and three nights I was free to do whatever I pleased. I woke up whenever I wanted, ate whatever I wanted (except for that blasted kale salad which could have been a carb.), attended events and site seeing at my leisure and on a whim, and stayed up late watching scary movies and catching up, yes, having face to face conversation with my husband. After the weekend was finished, I noticed a visceral change in my posture, facial expressions, mood, and mind.

I was recharged and refreshed in a way that my body desperately needed. I made the realization that this type of weekend is why I work, and I need to be cognizant of priding myself on “living to work“ so much that I run myself down, it’s not good for me, nor anyone as much as it might feel good to be a “hard worker.” My anxiety was significantly better after the weekend as was my sleep and stress levels. In addition to recharging my batteries, I reconnected with a silly little dream of mine since I was small, to find a real Halloween town. To find a place filled with magic, mystery, and coziness where one can enjoy the kid-like perk of no legitimate responsibilities, just fun…and a ton of candy.