A Guide to the 10+ Best Things to do in Sleepy Hollow

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Last Updated on March 16, 2021 by Sophie Nadeau

Situated just 30 miles north of New York City, Sleepy Hollow is a village which is to be found in the town of Mount Pleasant in Westchester County. Made world-famous thanks to a book of the same name, The Legend of Sleepy Hollow, by Washington Irving, today the town is one of the most popular places to visit in New York state. Here’s your ultimate guide to the best things to do in Sleepy Hollow, as well as travel tips and things to know before you go.

Lying close to the Hudson River, the village of Sleepy Hollow boasts just ten thousands residents or so, but is visited by countless others on an annual basis who are looking to experience the magic for themselves. The charming village is particularly busy during the autumn, around Halloween, and so be sure to plan accordingly.

Rather interestingly, Sleepy Hollow was first incorporated under the name of North Tarrytown in the latter half of the 19th-century, though this was changed in 1996 to reflect the traditional name for the area. Highlights of the village include the Philipsburg Manor House, as well as the Sleepy Hollow Cemetery, where Washington Irving himself is buried.

How do you get to Sleepy Hollow?

If you’re looking for a fantastic day trip from Manhattan, then it couldn’t be easier to get from the center of the city to Sleepy Hollow. You simply need to hop on a train at Grand Central Station and head to Tarrytown. The train trip takes around an hour. En route, you’ll be rewarded with beautiful views of the New York State countryside.

Best things to do in Sleepy Hollow

#1 Discover the Legend of Sleepy Hollow

Whether book, TV, or film is your preferred go-to medium, discovering the Legend of Sleepy Hollow prior to your visit to the village is an absolute must. The story goes that the local area is plagued by a Headless Horseman, alleged to be the ghost of a Hessian trooper… and I won’t spoil the plot further as it’s best to discover the tale for yourself!

#2 Visit Philipsburg Manor

One of the most historical locations in Sleepy Hollow is Philipsburg Manor, which dates all the way back to 1750 and was a milling and trading complex that was home to 23 enslaved individuals of African descent. If you want to learn more about the history of the complex, then you can embark on a paid historical tour. You can purchase admission tickets and learn more about the tour here.

Philipsburg manor house in New York

#3 Wander around Sleepy Hollow Cemetery

Of course, one of the most visited places in Sleepy Hollow is its sprawling cemetery, which is the final resting place of several notable people, including Washington Irving and Elizabeth. In total, around 45,000 people are interred in Sleepy Hollow.

The cemetery itself was established in 1849 as Tarrytown Cemetery and its name was only changed to ‘Sleepy Hollow Cemetery’ to posthumously honour a request made by Washington Irving. Since 2009, the cemetery has been listed on the National Register of Historic Places.

Entrance to the Sleepy Hollow Cemetery in Tarrytown, New York

#4 Visit the Old Dutch Church

Located adjacent to the Sleepy Hollow Cemtery, it’s hard to miss the spire of the Old Dutch Church, which dates back to the 17th-century. As well as the cemetery, the church is one of the key locations in the tale of the headless horseman.

The stone ecclesiastical building is the second oldest extant church and the 15th oldest extant building in the state of New York. Please note that the Old Dutch Church closes at 4:30 PM on a daily basis and so be sure not to get caught out by this fairly early closing time!

You should also note that the churchyard of the Old Dutch Church and the Sleepy Hollow Cemetery are not one and the same. Many visitors get confused and assume that the churchyard is the cemetery from the Legend of Sleepy Hollow Tale. It is not.

Old Dutch Church, Sleepy Hollow, New York

#5 See the Headless Horseman Bridge

Of the things to do in Sleepy Hollow which relate to the tale of the Headless Horseman, one of the most important pertains to the bridge which was key in the story. The real life bridge which inspired the gourd attack of Ichabod Crane is sadly no longer standing.

In the book, the bridge is described as wooden, and while a wooden bridge can be found in the Sleepy Hollow cemetery, this is not the same bridge that was described in the book. Instead, though the wooden crossing has long since rotten away, there is now a stone bridge in its place, with a metal plaque denoting that it’s “The Headless Horseman Bridge.”.

#6 Visit Washington Irving’s House, Sunnyside

Irving is often nicknamed the ‘Founding Father of American Literature’ and today history lovers have the opportunity to visit his former home turned museum, Sunnyside. Set amidst ten acres alongside the Hudson River, the house was constructed in 1835.

Before visiting, I really recommend reading a short amount about Irving’s life, so as to be able to put things into context when visiting his former house. You should also note that photography of any kind is not permitted within the house.

#7 Visit Kykuit, the Rockefeller Estate

Thanks to its ease of access to New York City and the rest of the New York State, many a wealthy businessman over the years has selected their base outside of the city to be Sleepy Hollow. The Estate was once home to four generations of the Rockefeller Estate and has since been turned into a house museum.

Constructed on the hills overlooking Tarrytown in 1913, the mansion is constructed in the Colonial-style. Among the collection, visitors can marvel at Ming dynasty porcelains, countless priceless artworks, and plenty of historic furniture. Paid tours takes place from Thursday through Sunday from May to November.

#8 Visit the Union Church of Pocantico Hills 

One of the better-kept secrets and hidden gems of Sleepy Hollow is the Union Church of Pocantico Hills. After all, though it is rather plain in appearance, the interior contains a rather unique secret:  stained glass windows by Henri Matisse and Marc Chagall.

Indeed, the rose window is Matisse’s final work, while nine other windows were created for the Rockefeller estate by Chagall. Please note that you must buy timed tickets in order to visit the interior of the church. Unfortunately no photos are allowed to be taken inside.

#9 Attend The Great Jack O’Lantern Blaze

If you’re planning to visit Sleepy Hollow in the fall (which will ensure that you get to enjoy all of the beautiful fall colors, albeit the village will be a little busier than during other times of the year), then you simply need to go for the The Great Jack O’Lantern Blaze.

The annual festival takes place in Croton-on-Hudson, which is around a twenty minute drive away from Sleepy Hollow itself, but is oh-so-worth it. During the event, over 7,000 hand carved pumpkins are illuminated and set against the backdrop of an 18th-century landscape. 

#10 Rockefeller State Park Preserve

Another acitivty to do close to Sleepy Hollow which is best done during the autumn is to visit the Rockefeller State Park Preserve, which can be found to the north of the village. The State Park lies in the eastern foothills of the Hudson River and comprises of 55 miles worth of carriage trails, which allow visitors to partake in activities such as horseback riding, hiking, cross country skiing, and sledding, among other things.

Rockefeller State Park Preserve

#11 Snap a photo of the Sleepy Hollow Lighthouse

Of all the places to visit in and around Sleepy Hollow, one of the most Instagrammable is that of the Sleepy Hollow Lighthouse. Also known as the aka Tarrytown Lighthouse and Kingsland Point Lighthouse, the beacon was once half a mile away from the shoreline.

However, silt and sand, and landfill from a since demolished factory have built up over the decades and so today the Lighthouse stands just a few feet away from the shoreline. Since retired, the lighthouse was in use for 78 years.

How to Visit the Sleepy Hollow Lighthouse

#12 Stay at the Castle Hotel and Spa

If you’re looking for the ultimate luxury while in Sleepy Hollow and wish to make a weekend of your trip as opposed to simply staying for a few hours, the best place to stay is the Castle Hotel and Spa. Set against the backdrop of a stone manor house, the Sleepy Hollow hotel boasts amenities such as an on-site restaurant, the Equus and a 24 hour fitness centre. Check rates and availability here.

Tips for visiting Sleepy Hollow

If you’re looking to enjoy the many attractions and things to do close by to Sleepy Hollow, then you may well want to consider spending the night in Tarrytown so as to make the most of your time in the area (and have the opportunity to see the town early in the morning, before the rest of the crowds arrive). Check Tarrytown hotel prices here.

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A Guide to the 10+ Best Things to do in Sleepy Hollow New York State USA

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