A lot of people don’t know this but Sleepy Hollow is a real place. Yes, it was also the setting of the fictional Headless Horseman story by Washington Irving. But the little village near Tarrytown in New York does exist and served as his inspiration.
Apart from the iconic Sleepy Hollow cemetery, church and bridge, there are other things to see in Sleepy Hollow and Tarrytown. Here’s a quick overview to make your trip upstate a memorable one.
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Is Sleepy Hollow real?
Everyone has heard of it, but many people wonder: where is Sleepy Hollow in NY? Sleepy Hollow was a fictional small village created by Washington Irving. He basically wrote about a place near his hometown of Tarrytown by New York State’s Hudson Valley.
However, the village North Tarrytown in Westchester County was officially renamed Sleepy Hollow in 1997, though it is believed that actually the town of Kinderhook was the original inspiration. Either way, so now there is an official Sleepy Hollow.
What is the Story of Sleep Hollow again?
In case you forgot, here is a refresher of the original short story “The Legend of Sleepy Hollow ” by Washington Irving. (Not the Tim Burton movie or the TV series.) He based his story in a town named Sleepy Hollow near Tarryown where supernatural things seemed rather common.
The particular incident he describes is the appearance of the damned soul of a former Hessian solider, locally known as the headless spectre “Galloping Hessian of the Hollow”. The main protagonist, lanky anti hero Ichabod Crane, visits a party at the Van Tassel mansion to try and court his crush.
His hopes are crushed and he rides off into the night, encountering the aggressive headless horseman by the bridge, who’s throwing his pumpkin head at the scared Ichabod! It remains unclear what happened to either those figures as Ichabod was never seen again.
How to Get to Sleepy Hollow
The town is an easy 30 minute ride away by car. If you intend to explore much of the surrounding area during your Sleepy Hollow travel, renting a car is highly recommended as public transportation options are limited once you are out of New York City.
To reach Sleepy Hollow from NYC by train, simply take a train on the Hudson line from Grand Central and get off at the stop in Tarrytown. Trains run every 30 minutes and cost $10-20 depending on the time of day.
When to Visit Sleepy Hollow
The town is sleepy indeed throughout the year with occasional events. Check the event calendar for details.
Still, THE best time to visit Sleepy Hollow is of course in autumn. Come for the special Halloween events to really get your spook on.
From spring to late autumn, you can join guided tours around Sleepy Hollow cemetery to learn more about the local history, literary heritage and see the tombstones of famous personalities and entrepreneurs.
For a Halloween worthy experience, head to Philipsburg Manor in October for its newly transformed haunted landscapes. It’s not for the faint of heart! There will be a headless Sleepy Hollow horseman and haunted trail waiting for you at Horseman’s Hollow.
Tarrytown NY Things to Do
Although it’s frequently overshadowed by the far more famous Sleepy Hollow, there are a few unique and exciting things to do in Tarrytown, NY too. Lyndhurst Mansion is a jaw dropping Gothic Revival mansion and one of the coolest Tarrytown attractions.
Surrounded by enormous evergreen trees, the estate spans 67 acres and seems straight out of a fairytale. Spend a peaceful day exploring the grounds and marveling at the stunning architecture.
Stone Barns Centre for Food and Agriculture
The Stone Barns Centre for Food and Agriculture is all about creating a sustainable food system. They invest in farming methods that are sustainable and healthy, with the goal of cleaning up the path food takes from the farm to our plates.
There’s so much to do at the centre if you’re interested in learning more about farming and natural foods. On weekends in the warmer months, enjoy pop up talks and informational guided tours of the grounds.
Check out the calendar on their website to stay up to date on what they’re offering during your trip.
This English manor takes you back to 1750, when the building was a thriving milling and trading complex, as well as a (forced) home to 23 African slaves.
The manor’s dark past may contribute to the eerie feel it gives off today, as it fits in very well with the rest of Sleepy Hollow’s vibe.
Tour the manor house and learn about a day in the life of those living and laboring at Philipsburg Manor. The manor is closed on Mondays and Tuesdays and is only open from May 1 to November 10 each year.
Have you ever dreamt of staying in a real castle? In the US that’s not as easy as in Europe but you can do exactly that in Tarrytown of all places. The historic Castle Hotel & Spa is a beautiful building.
Its rooms are a tasteful blend of old heritage and modern style, you can take advantage of the full-service restaurant and spa as well as the outdoor pool complex with its hot tub. Some rooms come with views of the Hudson River.
Breakfast is served on the Garden Terrace and you are only 3 miles away from John D. Rockefeller’s Kykuit estate. On Booking, solo travellers especially love this one-of-a-kind Tarrytown hotel. Reserve your spot here.
Union Church of Pocantico Hills
It might not look like much but the neo-Gothic Union Church of Pocantico Hills is linked to famous French artists Henri Matisse and Marc Chagall.
The former was commissioned to design a rose window in honour of the deceased wife of John D. Rockefeller, Jr, who had the church built in the first place.
When he himself passed, his children hat Chagall create a Good Samaritan window dedicated to him.
Sleepy Hollow Things to Do
Old Dutch Reformed Church
When travellers visit Sleepy Hollow, they will come to see the iconic sites. Especially the more creepy ones. The Old Dutch Reformed Church should be on the top of your things to see in Sleepy Hollow list.
This 17th century stone church is the building that inspired Washington Irving’s beloved tale! It stands at the start of the cemetery of Sleepy Hollow and is a landmark for sure.
On your visit, imagine Ichabod Crane leading the choir in the church, courting Katrina Van Tassel in the graveyard, and keep your eyes peeled for the Headless Horseman hiding between the tombstones.
You need a vivid imagination for this as on a sunny day, it looks very beautiful around here actually.
Sleepy Hollow Cemetery
Many famous figures have found their final resting places at the Sleepy Hollow Cemetery, including Washington Irving, the author of “The Legend of Sleepy Hollow.” His grave is clearly marked by flags and an information plaque.
The tombstone you see isn’t the original one as it has been chiseled down twice by tourists who wanted to bring home unique souvenirs. So now getting close is no longer possible. You can see Washington Irving’s grave through the iron fence, however. And that’s totally enough.
To learn the most about this spooky landmark, join one of many organized walking tours through the cemetery. Tickets should be purchased in advance as they tend to sell out quickly, especially around Halloween time.
When you arrive, pick up a Sleepy Hollow Cemetery map for free at the cemetery office or the cemetery’s south gate when the information booth is set up.
On it, you can see the location of other famous personalities’ graves, including Andrew Carnegie, William Rockefeller, Elizabeth Arden and Walter Chrysler. And of course, there are a lof graves by the Van Tassel family, which are mentioned in Irving’s short story.
Kykuit – The Rockefeller Estate
There is absolutely no shortage of things to do in Sleepy Hollow. Kykuit, also known as the John D. Rockefeller Estate, is a 40 room mansion that housed 4 generations of Rockefellers. The former home is now a historic site and is open to the public for tours.
Kykuit represents decadence at its finest. The house also has magnificent gardens and even several art galleries. Several tour options are available, and they range in price from $15-40.
Sleepy Hollow Lighthouse
This spark plug lighthouse sits on the east side of the Hudson River. It was built in the 1880s and was added to the National Register of Historic Places in 1979.
A spark plug lighthouse (also known as bug light or caisson lighthouse) has the spcial feature of resting entirely on a concrete or metal watertight structure.
It’s the only spark plug style lighthouse to contain family housing, making it a unique find for anyone interested in the history of lighthouses. Guided tours of the lighthouse are available on select days for $5 per person.
Sleepy Hollow Bridge
When you cross the main bridge of Sleepy Hollow, you will see a sign telling you that this was the site of the famous bridge crossing by Ichabod Crane.
The original bridge is long gone and I’ve heard that the actual location is still a little bit farther and not exactly where the traffic is nowadays.
Rockefeller State Park Preserve
This picturesque park near Sleepy Hollow village offers a plethora of varied activities. At the park you can go horseback riding, jogging, bird watching, carriage driving, fishing, and more.
These quiet countryside grounds are beautiful and meditative and make for a great relaxing time after a your time sightseeing Sleepy Hollow.
Visiting the Rockefeller State Park Preserve is an excellent way to relax and unwind or to get active during your trip to Sleepy Hollow, NY.
Sleepy Hollow is quite sleepy indeed throughout the year but come Halloween, the village lives up to its hype. A headless horseman rides the town, a field of pumpkins is illuminated, there are haunted tours and houses to attend…
It’s one of THE best places to be for Halloween in the US and as a result gets packed. So plan your trip in advance and make any hotel reservations asap.
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