I have been wanting to visit Sleepy Hollow since we moved to New York. I’ve always been fascinated with the legend of the Headless Horseman in the timeless book, The Legend of Sleepy Hollow. This past weekend, we finally had the opportunity to go.
There isn’t a lot of information about Sleepy Hollow available on the internet. It’s not a “must-stop” for New Yorkers. Because of this, I was a little nervous about hopping off the train at Philipse Manor. Would it be a literal ghost town? Would it be safe? Would they welcome out-of-towners? Would it be walkable?
Train travel is amazing. We prefer it over driving almost any day. However, if you get caught in a sticky situation, you’re there for at least an hour until the next train rolls through… Hopefully I’ve planned accordingly! 😂
As soon as we stepped off the train and crossed the street, a set of old stairs led us up the cliff to the historic town. As we reached the top of the stone stairs, we were amazed at how beautiful it was. This is a very well-to-do and well-kept community. Legends be damned – these residents are proud – and deservingly so. The yards were meticulously maintained. And, our pathway was covered with beautiful fall leaves on the way into the historic downtown, yet the leaves were cleared within an hour of our walking back to the train. There were people working in their yards and waving at us or saying “hello” as we passed by. This is a lovely and warming community.
As we arrived at the main road, we stood staring up at the graveyard, which sits on a stone wall about 15 feet above the road. This is certainly the primary point-of-interest. The community may be lovely, but there is an unmistakeable past. And, the legend lives.
All of the primary sights are within a quarter-of-a-mile from each other. You’ll pass by the Sleepy Hollow Cemetery where Washington Irving, Andrew Carnegie, Walter Chrysler, Samuel Gompers, Elizabeth Arden, Leona Helmsley, Brooke Astor, and William Rockefeller are buried. Then, you’ll see a humble church. The Old Dutch Church has been in Sleepy Hollow since 1685. It was built by Frederick Philipse, a rich merchant and trader.
This church and the yard surrounding it were the inspiration for Irving’s “The Legend of Sleepy Hollow.” The church is still active, and you can join the congregation for services at any scheduled service time, or for tours throughout the month of October, on Christmas, throughout the summer music festival, and at Easter.
Just past the church, you will stumble upon a bridge – yep – you guessed it! The Headless Horseman Bridge. Although not the same bridge as would’ve been here in the 1800s, this bridge was erected in the same spot as the horrifying tale. However, I didn’t hear any hooves…only the trickling of the creek below.
The last primary point of interest for tourists is the Headless Horseman Sculpture just across the street. A work of modern art, this sculpture brings the Headless Horseman to life in the middle of town.
Other cool items to see and do would be the lighthouse, checking out where all of the movies have been filmed (including The Legend of Sleepy Hollow, The Preacher’s Wife, The Thomas Crown Affair, Mona Lisa Smile, and The Good Shepherd, among many others!), and all of the historic mansions in the area.
The Blaze at Van Cortlandt Manor
We had heard that there was a fun jack-o-lantern festival near Sleepy Hollow at the Van Cortlandt Manor. Being a big follower of all things kitschy, I had to check it out. I went to buy tickets for Halloween weekend on the last weekend of September. It was sold out until the middle of November. Halloween would be long over, but we were still going anyway!
We anticipated lots of plastic/metal/ceramic pumpkins and lights strung up in a garden area. We thought there would be some fun things to see, but we didn’t expect much. It’s a themed-festival…We’ve all been to them… Right??
Wrong. This was quite possibly the biggest shrine to the art of pumpkin carving that we’ve ever experienced, and never imagined. The entire event was made of live pumpkins – carved specifically each year for this event. There are more than 7,000 pumpkins carved by hand for the event each year. And, we’re not talking about the standard jack-o-lantern; these are full-on art installations with multiple pumpkins being used to create each piece. There were even pumpkins on motors to create a functioning windmill and vintage-carousel.
If you have the opportunity to check out The Blaze someday, you certainly should! If not, let these photos offer you some inspiration for your next Halloween decorating and pumpkin carving.
Other NYC Ideas…
Check out our previous posts for other NYC neighborhoods to check-out!
- Long Island City, Queens
- North Fork, Long Island
- Red Hook
- Rockaway Beach
- Murray Hill and Midtown East
- Central Park
- Discover the Best NYC Landmark and Lookout – Just For You!
- Spookiest Spots in NYC
More coming each week!
And…it’s 2020…So, here’s my weekly reminder.
Should I Come to New York in 2020?
If you are living outside the Northeast, the answer is still, sadly, no. For more on this, check out our other posts on 3 Months of New York City, Riding the Second Wave, Wandering and Wondering in NYC, and New York: Awakening from COVID-19 Slumber. Although the numbers are starting to climb again, New York still seems to be under control (at this point). The government is doing its best to make sure it stays below a certain percentage. With so many people living in such a close proximity, pandemics are especially lethal here.
***UPDATE*** Starting on November 4th, the mandatory 14-day quarantine has ended! New York is moving to a test-based travel restriction. You have to show a negative COVID-19 test result from the past 72 hours upon arrival, then, three days after arrival (and quarantine), you have to receive another test here. If it’s negative, you’re good to go. If it’s positive, you must continue to quarantine. So, this means shorter quarantines (yay!), but two tests… Stay home if you can…If you can’t, you’ve been warned!
Wait this one out…New York will still be here when the dust settles.
As always, don’t forget to Toast The Moon to all of your international travels by visiting our store, and make sure to follow us on Facebook, Twitter, and the ‘gram to catch all of our latest posts and adventures!
Stay in your region this year, stay safe, stay distant, and be like the NYC statues – wear your masks! We’ll see you on the other side.
Noah and Majhon