There is Nothing Sleepy About Sleepy Hollow, NY on Halloween

My kids, ages almost 8 and 9, are finally getting old enough to enjoy the creepier parts of Halloween. Nothing violent, of course, but just scary enough that they can enjoy it without too many nightmares. Last year we went to the Pumpkin Blaze in Sleepy Hollow, NY which is around 45 minutes from our home. This was an amazing experience but definitely rated G. They would have enjoyed doing that again, heck, I loved it, but I thought we needed to step it up a notch. I did some digging and discovered The Sleepy Hollow Experience, performed in Sleepy Hollow, NY on Halloween.

The Sleepy Hollow Experience is an immersive, theatrical reenactment of Washington Irving’s The Legend of Sleepy Hollow. You know the story, this gawky guy takes a walk through the woods at night, runs into the headless horseman and… well, I won’t spoil the ending for you. Anyway, The entire evening went off without a hitch from dinner to the drive home and the kids had a blast. They were only mildly frightened.

Get Ticket FAR in Advance

I am on the Sleepy Hollow Facebook page which gave me a heads up when the tickets went on sale back in August. There are only so many performances during the weeks leading up to Halloween, so be sure to get them far in advance. I decided the kids were old enough for the 8:30 PM show and I wanted to make sure it was extra dark and spooky.

Bundle Up

The temperature was supposed to drop to 40 degrees that night and I didn’t want any complaining so we dressed everyone in jeans, sneakers and sweatshirts and brought along jackets, hats, gloves and scarves. The entire event takes place outside, on the property of Washignton Irving’s Sunnyside, which was his home when he wrote the story.

Keeping Hunger at Bay

When we went to Sleepy Hallow last year, we discovered that restaurants in the area are few and far between. They have an influx of tourists at this time of year and not enough eateries to go around. There are neighboring towns, like Terrytown and Irvington, but these places are also packed, trying to handle the masses of Halloween visitors. I wasn’t worried. I had a plan. We left the house at 4:45p and got to The Bridge View Tavern at about 5:30. There was a line outside, which was what I was expecting. The owner came out a number of times and encouraged people to find food elsewhere if they didn’t have a Halloween event to go to. Wait times were between an hour and an hour and a half, depending on group size. We had plenty of time so I wasn’t worried and I find that we are usually seated much earlier than the wait time suggests.

We chit-chatted with the people in front and behind us in line. One group was going on a far scarier Sleepy Hollow Experience with a little more blood and gore… maybe in five (ten?) years, I thought…. The group in back of us decided to check the availability of the restaurant next door and when the hostess informed them there was no room, they grabbed a handful of mints on the way out the door, which they generously shared with my kids. Not long after, we were seated, waiting only about 20 minutes.

They put us in the heated outdoor beer garden which was cozy and full of character. The kids loved the numerous license plates adorning the walls and the colored lights enveloping the trees. Our waitress was spunky, lovely, and accommodating. She attended to our every need, even with the mass of patrons she juggled.

The kids shared a burger, my mother got a shrimp po’ boy and I got fish tacos, all of which were outstanding. Apple cider sangria for my mom and I and hot virgin cider for the kids was a tasty autumn treat. We waited a bit longer than average for the food, but it was nothing I wasn’t prepared to handle and the kids had plenty to distract them from their hunger between the ambiance, people and the fun conversation. All in all, it was an excellent dinner and we were back in the car with an hour to spare before the Sleepy Hollow Experience.

The Sleepy Hollow Experience

It was about a 10-minute drive to Washington Irving’s Sunnyside from The Bridge View Tavern. We drove down a dark road and parked where directed. There is really nowhere to kill any time and we had about half an hour, so we sat in the car until the previous group let out and we could get in line. Once there, everything moved quickly. We were led down a dark, shadowy path lit only by the dim flicker of candlelight. I’m always amazed at how brave my kids are compared to myself as a kid. At their age, I would have imagined things lurking in the shadows, ready to spring out at any moment. If they have any of these fears, they don’t show it.

We broke through the darkness to an area that is covered by a tent. There is a table selling snacks and drinks and a gift shop, of course. There are portraits hanging from the ceiling and an old-fashioned writer’s desk at the heart of the space. It has papers and books strewn across it, a quill and ink, and candles illuminate the surface. Black cloaked, masked figures wander through the crowd, gazing ominously.

Without warning, a tall, dark haired man dressed in the 1800s garb sat down at the desk and started to write. This was Washington Irving, himself, writing his story. Sporadically, he noticed the surrounding crowd. He was surprised and a little nervous when he saw the flash of a camera phone. When he observed my son staring at him, unabashed, he greeted him with a “good evening, young sir”.  My son laughed nervously and mumbled “good evening”.

When the time came for the performance to start, we were led down another dark and windy path by the cloaked masked figures. The scent of horse manure and candle wax engulfed us. It was pitch black other than the lanterns lighting our way. We stopped in front of an ancient manor house. Suddenly, the door opened and four figures emerged. They were ghostly and sallow. Their period clothing was dirty and tattered. They made jerky movements as they walked and at certain points, looked as though their bones could barely support them. It was spooky to say the least and at this point, I wondered if I had made a mistake bringing the kids. All at once, one of the female characters broke into song, and the story began. We met Ichabod Crane, the school teacher who was new in town, Katrina Van Tassel, his love interest and Abraham “Brom Bones” Van Brunt, the competition, also vying for Katrina’s affections. The Old English language was a bit heavy for the kids but they got the gist.

We followed the actors through the story of The Legend of Sleepy Hollow and watched it unfold. We saw Ichabod’s school house and observed “Brom Bones” Van Brunt’s jealousy grow. We went to a party at Katrina Van Tassel’s house where they told ghost stories that piqued the nerves of Ichabod’s overactive imagination. We anxiously followed him through the dark woods to his alleged demise. I don’t want to give too much away!

The performance was Broadway quality. The actors were truly believable and extraordinarily entertaining. The story was creatively interpreted.

Following the finale, my daughter did say she was ready to go home and it took her an extra few minutes to get to sleep that night, but both kids thoroughly enjoyed themselves, we all did. It is an experience none of us will ever forget.


    1. Gin

      Thanks so much for the kind words! Sleepy Hallow is amazing! I did reviews on some other cool locations in the North East for Halloween, if you are interested. Such an awesome time of year! Check back often. I am adding stuff all the time!

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