15 Best Things to Do in Sleepy Hollow, NY

Sleepy Hollow, NY
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The village of Sleepy Hollow lies at Westchester County, New York, in the town of Mount Pleasant.

It has a well-deserved reputation for being haunted.

The ancient village immortalized in Washington Irving’s short fiction published in 1820, entitled “The Legend of Sleepy Hollow,” has long been a popular tourist destination.

Incorporated in the late 19th century as North Tarrytown, the residents changed the name to Tarrytown in 1996.

As a homage to Irving, who grew up in Tarrytown and now rests at Sleepy Hollow Cemetery, people regarded the place as Sleepy Hollow.

Sleepy Hollow is known as one of the world’s most haunted locations.

Ironically, Sleepy Hollow has also been named “America’s safest little city.”

Despite the spooky story surrounding the village, there is so much more to Sleepy Hollow than we think.

Located on the Hudson River’s banks, the Sleepy Hollow of today provides breathtaking views, a historic downtown, and a pleasant family atmosphere that is common to many Hudson Valley small towns.

In its early days, Native American tribes inhabited the area and afterward by European settlers.

The Rockefellers, basically New York’s royal family, made the village a part of their treasured residences.

In addition, because so much of the surrounding land is a protected property, tourists and locals alike will have plenty of opportunities to explore the area.

The best part is Sleepy Hollow’s attractions are within walking distance from one another.

Excited to discover what this historic village has to offer?

Here are the 15 best things to do in Sleepy Hollow:

Explore the Grandeur of Kykuit Estate

Outside of Kykuit Estate
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You do not want to forget the magnificent Rockefeller family’s Kykuit Estate.

Kykuit is one of many magnificent homes and estates that visitors to the Historic Hudson Valley can view.

The Rockefellers are the closest to New York royalty that you can imagine.

Standard Oil’s founder, John D. Rockefeller, built his fortune in the petroleum business throughout the nineteenth century.

A Statue in Kykuit Estate
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The Rockefeller family has left a lasting imprint on New York City and the Hudson Valley.

John D. Rockefeller commissioned the construction of the colonial-style house in 1913, and it now sits perched high over Sleepy Hollow and Tarrytown.

It stands six stories high, with ivy covering the front and stone arches, and the gardens are immaculate.

In addition to the outside, the interiors are also lovely.

The Rockefellers’ private collection of contemporary art, including Picassos and Andy Warhol, is housed beneath the mansion’s basement.

Inside Kykuit Estate
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Now, however, the home is available to the public, despite its continued ownership by the Rockefellers.

There are various ticket choices available for the Kykuit Estate.

The Classic Tour is less expensive and briefer.

Meanwhile, the Grand Tour covers much more ground, including an upper floor, but tickets were much more costly, and excursions lasted longer than two hours.

Stroll Along Sleepy Hollow Main Street

Sleepy Hollow's "Beekman Ave" main street is worth a visit in October when the town clock is decked with "Jack" the scarecrow.

Seeing their orange street signs and noticing the various allusions to the ancient horseman mythology is an experience.

As an illustration, look at the firetrucks, which prominently display him on the side of their vehicles.

Visit Sleepy Hollow Cemetery

Outside Sleepy Hollow Cemetery
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Our first stop is Sleepy Hollow Cemetery, a must-see destination for horror and history enthusiasts alike.

Established in 1849, the Sleepy Hollow Cemetery serves as the nexus for many of the village’s historical origins.

It’s hard to believe, but this cemetery covers an area of over 90 acres, making it doubtful that you’ll see it all in one visit.

Learn about prominent people buried at Sleepy Hollow by visiting their gravesites, such as William Rockefeller and Washington Irving.

Angel in Sleepy Hollow Cemetery
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The cemetery is one of the New York State and National Registers of Historic Places.

Sculptures dot the landscape, as do magnificent mausoleums, and the Hudson River is only the beginning.

The Pocantico River meanders through the cemetery, adding to its allure.

You may purchase tickets for tours of the cemetery, such as the Classic Evening Lantern Tour, which visits the graves of the cemetery’s most notable inhabitants.

You may also try the Legend of Sleepy Hollow tour, which focuses on Irving and his legacy.

Bring Home Fresh Produce from the Tarrytown-Sleepy Hollow Farmers Market

The Tarrytown-Sleepy Hollow Farmers Market plays an important role in the Hudson River region.

Every Saturday, the market opens at Patriots Park which lies between Sleepy Hollow and Tarrytown.

It features fresh fruits, pieces of bread, baked products, meats, cheeses, homemade meals, and more.

There are around 30 merchants selling their products throughout the park.

There's always something going on, from chef demos and kid-friendly events to painting workshops, in addition to the diverse array of colorful products.

Residents and visitors alike enjoy the annual Tree Lighting Festival and Christmas pop-up stalls that the farmers market hosts during the holiday season.

Pray at the Historic Old Dutch Church

Outside historic Old Dutch Church
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The Sleepy Hollow of Washington Irving’s day was a real place, and it served as inspiration for the Headless Horseman story he wrote.

In the story, Ichabod Crane has to go to the church to escape the Horseman’s grasp.

The Old Dutch Church in Sleepy Hollow is the actual church mentioned in the story, which also happens to be New York’s oldest church.

Old Dutch Church in Sleepy Hollow
Daniel Case, CC BY-SA 3.0, via Wikimedia Commons

It was established in 1685 and is still going strong today.

The church was designated a National Historic Landmark in the 1960s.

In the fall, hundreds of people flock to the church and surrounding area to see the frightening sight and participate in the seasonal activities that celebrate its well-known folklore.

Learn New York’s Past at Philipsburg Manor

Outside View of Philipsburg Manor
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Philipsburg Manor is a great site to see what New York used to look like in the mid-18th century.

Once known as Philipse Manor to the European settlers who lived there, the site now takes visitors back to 1750, when it was a thriving gristmill.

In addition to the mill, farm, and manor home, the Philipse estate encompassed 52,000 acres along the banks of the Pocantico River.

There was a dark side to the Manor as well, as 23 slaves of African ancestry lived there.

Outside Philipsburg Manor
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Today, the Manor functions as a living museum to educate visitors about slavery in the United States and agricultural life in the 18th century.

In addition to exploring the Manor’s façade, you may also explore the Manor indoors, where you will find replicas of the period’s antiques.

Staff dressed in period costumes commemorate the Philipse family and recount their story.

Watch the Unsilent Picture

Want to discover even more of what Sleepy Hollow has to offer?

To see something fresh and exciting, check out Unsilent Picture!

Instead of an Irving short story, "The Adventure of the Mysterious Picture" serves as the inspiration for this film.

Live music, such as accordion, cello, and electric guitar, accompany the silent film on one side of the screen, resulting in an unsettling soundscape.

A Foley artist, on the other hand, creates real-time sound effects like footsteps or a glass breaking.

What we have here isn't simply a movie; it's an amazing live performance that's unlike anything else.

The 40-minute short film runs at Philipsburg Manor's 444-seat tent theater.

Cross the Spooky Headless Horseman Bridge

A Sign in Sleepy Hollow Bridge
Gryffindor, CC BY-SA 3.0, via Wikimedia Commons

We learn about the Headless Horseman's most common haunting in Washington Irving's The Legend of Sleepy Hollow.

The Sleepy Hollow Bridge turns out to be a true landmark.

Although the bridge is not the same as the one built during Washington Irving’s period, it crosses the Pocantico River on the grounds of Sleepy Hollow Cemetery in a similar manner.

The actual contemporary bridge is long and wide, but in cinematic versions of the legend, a more romantic and frightening covered bridge is shown.

In today's world, a historical marker claims to show that the current bridge is located precisely where the fabled one once stood, although this isn't entirely true.

It would take half a mile or so to get there.

Legend has it that the Headless Horseman chases Ichabod Crane through the woods until he is ultimately captured on a wooden bridge across the Pocantico River.

Here's where the Headless Horseman tosses a pumpkin at Crane, and in the morning, all that's left are the saddle scraps and the shattered pieces of the pumpkin.

Take Photos With the Headless Horseman Statue

Because of the statue's location in the middle of a busy highway, you should exercise caution when stopping here.

But it is worthwhile to make the detour at this spot.

The statue is only a few minutes' walk from the Old Dutch Burying Ground.

After viewing the location of the original Headless Horseman bridge, continue walking and you will soon come upon the statue.

Climb Up Sleepy Hollow Lighthouse

Outside View of Sleepy Hollow Lighthouse
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The Sleepy Hollow Lighthouse, also known as the Tarrytown Lighthouse and the Kingsland Point Lighthouse, although they all refer to the same historic site.

Since its construction in 1883, the lighthouse has kept a watchful eye on the Hudson River's eastern shoreline for potentially hazardous situations.

The lighthouse used to include five floors of living space, including a kitchen, and a dining room.

It also has a living room, three bedrooms, a work room, and a tiny watchtower chamber on the top.

The lighthouse's light used to be red, but the owners changed it to a revolving white light in 1902.

In the 1950s, the lighthouse became mechanized, but before that, it had a history of 12 lightkeepers and their families living in the tower.

When the Tappan Zee Bridge opened in 1961, the lighthouse became obsolete.

Today, tourists may explore the lighthouse and learn about its history while posing for photographs from some of the greatest vantage spots along the Westchester RiverWalk.

Other Things to Do Nearby

Wander Around Rockefeller State Park Preserve

Rock Bridge in Rockefeller State Park Preserve
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A five-minute drive from Sleepy Hollow, Pocantico Hills and Rockwood Hall County Estates now constitute part of the Rockefeller State Park Preserve.

Once owned by John D. Rockefeller, it is located north of Sleepy Hollow.

The Rockefellers turned the 1771-acre preserve over to New York State as a way to protect its natural beauty and wildlife for future generations.

The Beauty of Rockefeller State Park Preserve
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You may walk around Swan Lake and the Pocantico River, over stone bridges and picturesque views.

Here, you will see various animals, including 202 different kinds of birds, as well as amphibians, fish, and monarch butterflies.

Even today, the ancient Rockwood Hall mansion is still visible from the Hudson River and the Palisade Cliffs that lie on the other side.

From 1886 through 1922, William Rockefeller lived at Rockwood Hall's 202-room home.

A Tunnel Rockefeller State Park
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Check Out the Sunnyside House of Washington Irving

Outside view of Sunnyside House
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Five minutes away from the Sleepy Hollow, Sunnyside was Washington Irving's Tarrytown home when he wrote The Legend of Sleepy Hollow.

In the 1960s, it was recognized as a National Historic Landmark.

It was formerly a part of Philipsburg's Manor.

Irving bought the two-room Dutch stone home on the Hudson River in 1835 for $800.

He added Tudor-style chimneys, gable ends, Gothic windows, and a Spanish-style bell tower.

He was also involved with the landscaping of the property.

The ice house at Sunnyside
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Many of the original furniture is still in the home and gardens, which have been restored to their 1850s appearance.

The estate is a popular tourist destination for anyone interested in learning about Washington Irving's life and times, as well as the local legends and history.

The mansion, on the other hand, is said to be haunted.

On Halloween, it's a favorite destination for people searching for shivers.

While it may have a spooky reputation, the lovely grounds and well-preserved buildings make it a great spot for a picnic.

The inside of the home feels like a time machine transported back in time.

A tour guide dressed as one of Washington Irving's characters accompanies you through the museum to get to know each area.

Even if you've never read anything by the author before, you'll like this tour.

Tour the Tarrytown Music Hall

Outside View of  Tarrytown Music Hall
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Just a three-minute drive away from Sleepy Hollow, many people think that the Tarrytown Music Hall is haunted due to its deep history.

Completed in 1885, the Music Hall has served as a place for entertainment for some of the village's most renowned residents, including the Rockefellers.

Outside View of  Tarrytown Music Hall
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It has also functioned as a forum for numerous national causes, a movie theater, and is currently a performing arts center.

Ghost tours and paranormal investigations are also available at the Music Hall on several occasions.

Stay at Castle Hotel & Spa

Have you ever been to a castle?

How about a castle-turned-hotel?

Few hotels and spas in the Hudson Valley can match Castle Hotel & Spa in terms of sheer luxury.

The massive stone mansion is perched atop a bluff above the Hudson.

The estate has 31 guest rooms and suites and is a member of Small Luxury Hotels of the World.

It features a 24-hour fitness facility, whirlpool, and groomed jogging pathways, so guests don't have to miss out on anything.

The hotel's well-known Equus restaurant has gotten four diamonds from AAA.

In addition, the Sankara Spa is among the best in the area.

Castle Hotel & Spa makes a great home base from which to explore Sleepy Hollow which is roughly six minutes away from the hotel.

Experience the Great Jack O’Lantern Blaze

Lights in  Great Jack O’Lantern Blaze
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To get to Croton-on-Hudson, you'll have to make the twenty-minute trip.

Keep going despite the distance; it would be a real pity to miss this magnificent display of pumpkin lights.

You'll walk through a beautiful park of 7,000 illuminating pumpkins at Blaze.

The place will transport you into a scene from Tim Burton's The Nightmare Before Christmas.

Pumpkin Museum of Art, windmill, two beautiful bridges, and the enormous Statue of Liberty are just a few of the jack-o-lantern-themed attractions you'll find throughout the area.

Final Thoughts

As you may know by now, New York isn’t all about skyscrapers and crowded streets.

Here, a peaceful, historical village awaits you, which is only a train ride away from Grand Central Station.

However, if you're going during the Halloween season, be sure to reserve your tickets in advance.

Despite the seemingly limitless number of events in the village, some venues are enough to cover a particular number of visitors with a limited number of tickets available.

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