Sleepy Hollow: More Than A Legend

Last updated on January 7, 2020.

Just like Salem was on my travel list for years, so was Sleepy Hollow. The classic tale turned movie by George Washington Irving has always been a favorite of mine, and I was always intrigued to visit the town of inspiration! Slightly north of Sleepy Hollow is Croton-on-Hudson, home to The Great Jack O’Lantern Blaze.

When I saw that my cousin was interested in the blaze on Facebook, I immediately had a trip itinerary brewing! We got together a bunch of the girls in the family and headed down to Sleepy Hollow for a weekend earlier this month. I’m really happy with the timing of our trip; it was almost two weeks after Halloween. That meant that the crowds had died down (the opposite of our trip to Salem) and the fall colors were gorgeous. So if you’re planning a trip to Sleepy Hollow – early November is perfect!

Originally published January 16, 2018. Most recently updated January 7, 2020.

First Stop: Brewery!

Our first stop on our trip was at Captain Lawrence Brewing Company. The parking lot isn’t quite big enough to handle it’s popularity, so be careful if you’re planning to park on the road.

Since it’s recent expansion, Captain Lawrence retired its beer token system and now offers typical flights and pints. More options are available in cans and bottles to go. I was a bit disappointed that the Imperial “Rye”der (a seasonal pumpkin beer with a local Sleepy Hollow theme) was not available to sample, but it worked out for the better since I could bring it home to share with my husband and our friends. It was pretty good!

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I have to say the food was the highlight of the visit. My cousins loved the chicken wings, while I thought that the cornbread was great! We also split a huge order of truffle fries – yum! It’s counter service with a buzzer; so you order and then find a spot to sit. While it was a bit too brisk to sit outside, we didn’t have much of a choice because the inside was very crowded. But there were plenty of tables outside and even cornhole (if we hadn’t been too cold!).

The Great Jack O’Lantern Blaze

If you’ve never heard of The Great Jack O’Lantern Blaze, you’re missing out! So listen closely… I’d heard such great about the blaze for years. Every Halloween I’d want to go, only to realize too late that I’d already made plans or the tickets were sold out, or some other lame excuse. But this year was different. I made a point to buy tickets well in advance (this is SUPER important!) and make all of the arrangements. That way we were able to sit back and relax in anticipation of our upcoming girls’ weekend in Sleepy Hollow.

Important Things to Know

There are a few things you should know before visiting the blaze, and their FAQs are pretty humorous to read! First, you MUST buy your tickets in advance. They do sell out! Get there early. By at least an hour. They are not kidding when they say that the traffic gets backed up – majorly. Dress warm! It gets pretty chilly in New York in the fall. Unfortunately the blaze is not pet-friendly, but it is handicap accessible.

Another important piece of advice: bring a camera! The blaze is absolutely stunning to photograph – and it’s not only allowed, but encouraged! Just avoid heavy flash. Lastly, give yourself time to enjoy it. The blaze takes about an hour to walk through if you take your time to enjoy it and take photos. At the beginning/end there is a gift shop and a few pop-up cafés with food and drinks.

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Highlights of the Blaze

I can’t say enough about just how amazing the blaze was. Having high expectations going there, they were far exceeded. I just sat there in awe from the very first moment. Even the walk leading into the event is lined with pumpkins carved into lanterns and street lights – amazing! Every corner of the blaze has a theme and there is so much to see. Thousands and thousands of pumpkins, both real and fake, are hand-carved to create this incredible experience. A few of my favorite parts included the planterium, the headless horseman’s path, and the VanCortlandt Manor – all of which are accompanied with light displays that change. Another necessary photo is on the “PumpkinZee Bridge”, designed as a replica to the nearby Tappenzee Bridge. Enjoy every moment; it’s a truly amazing experience!

Sleepy Hollow Cemetery

The following morning we headed to Sleepy Hollow Cemetery for a tour. Located right behind the Old Dutch Church, the cemetery spans over 90 acres. You could easily spend the majority of your day there – and it is so photogenic! Especially in the fall with all of the trees changing colors. Also, from the highest hill in the cemetery you can even make out the faint skyline of New York City on a clear day!

Book a guided tour

While you could explore the cemetery (for free!) on your own, I highly recommend the tours put on by the cemetery. They offer tours both day and night. We chose the Original Knickerbocker Tour – only $10 for an hour-long informative tour on a Sunday morning. Our tour guide was fantastic; she lived and breathed the history of Sleepy Hollow. She knew so many of the stories that make up the area’s rich history.

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Along the tour we learned about Washington Irving, author of The Legend of Sleepy Hollow, and his life in the area. It was very interesting to find out about his house and the eventual train tracks laid down beside it. Irving was so unhappy about this that the railroad company made several agreements with him, including adding a train stop right at his house!

Further into the cemetery are several vaults built into the hillside. Our guide explained all about the symbolism seen on the doors and tombstones. One of the vaults had an hourglass as its handle – an indication that time had run out. We were able to enter one of the mausoleums, inside which was an open vault. The vault had a flower and a frame of Barnabas Collins – enshrined for the memory of the television series and film Dark Shadows. We learned so much along the tour; you’ll have to experience it yourself to learn it all!

The Old Dutch Church

As we neared the end of the tour, our guide gave us some information about the Old Dutch Church and its Burying Ground. Since they each run their own tours, she was unable to take us in there herself, but gave us information about the gravestones of importance. Most of Irving’s stories, particularly The Legend of Sleepy Hollow, are based off of real people buried there. Surprisingly, there is no one with the name “Katrina Van Tassel”, the heroine of the novel. But, you will find a Caterina Ecker who later married a Van Tessel. And there is also an Eleanor Van Tessel in a family plot on the side of the church. Locals think that Irving was fond of the name Katrina, but took the characteristics of Eleanor for his story. No matter the reasons, the history is amazing to walk through. And an added bonus – the shed in the burying ground is covered with old Dutch clogs! Beautiful.

Next to the cemetery you’ll find the Headless Horseman Bridge – where the horseman was said to have crossed into town as he looked for victims. Another few steps and you’ll be at the headless horseman statue. It’s a metal statue on a small plot of grass next to the main road. Good for a quick photo opp and then move along.

More Sleepy Hollow Wonders

Did you know that the town of Sleepy Hollow did not exist as such until after the novel? Part of Tarrytown was renamed in honor of Irving’s legend (and to put the town on the map!). But the legend isn’t the only famous piece of town; there are several mansions and other buildings to visit. I’m still waiting for the Sing Sing prison to be turned into a museum, but for now there are many mansions worth visiting. Fun fact: you can visit the grounds of the Lyndhurst Mansion for free! You only need to purchase tickets if you are going inside for a tour. But walking around the lawns and taking photos of the gothic castle are completely free! And highly recommended.

I hope you’ve enjoyed learning all about Sleepy Hollow and its many wonders. Have you ever been? Let me know in the comments below!

Can’t get enough cemeteries? Check out my post about visiting the two most famous cemeteries in New Orleans.