5 awesome things to do in Sleepy Hollow, New York’s haunted hamlet

Get ready for things to get a little spooky with Watt Where How’s Top Things to do in Sleepy Hollow.

Sleepy Hollow the book, the movie, the legend, and the small town in Westchester County, New York, all owe their fame to author Washington Irving – but there’s more than just haunting tales of pumpkin slinging horsemen to attract you. Top things to do in Sleepy Hollow include visits to open-air museums, a Rockefeller estate, and fun Halloween events.

The 1820 story, The Headless Horseman’s roots are said to date back to 1798 when the younger Irving escaped the Yellow Fever outbreak by heading north from New York City’s cramped neighborhoods.

Sleepy Hollow is a picturesque area on the east banks of the Hudson River, just north of Tarrytown, and at the time, it was an area rich in farmlands and later, opulent mansions, like the Lyndhurst Mansion, Kykuit (the Rockefeller Estate), and The James House Mansion. But it’s only relatively recently that locals changed its less appealing name from North Tarrytown to Sleepy Hollow to benefit from the connection with the legendary tale.

Interestingly, Irving’s other famed story, Rip Van Winkle dominates the local tourist trails of the northern Catskill towns.

The Legend of Sleepy Hollow

As mentioned above, Sleepy Hollow was renamed from North Tarrytown during the 1980s, to ride on the coattails of a certain headless horseman. Around the area, you’ll find historic landmarks, two different sculptures, and come each October, a range of spooky family events around the Philipsburg Manor.

The actual story is said to be based on an actual Hessian soldier decapitated by a cannonball during the Battle of White Plains, conveniently around Halloween 1776. Set in 1790, Washington Irving’s tale is about a new schoolmaster, Ichabod Crane, who falls for a young heiress and student, Katrina Van Tassel, who is also being pursued by another suitor, Brom Bones, an early Dutch settler. Upon leaving a party at the Van Tassel home, Crane is chased outside the cemetery by a headless horseman, pursued over the bridge, where the horseman throws a pumpkin at him, knocking him off his horse, never to be seen again.

Headless Horseman Sculpture

Weighing in at 11-ton and standing 18-feet tall, the rusty steel sculpture depicts the Headless Horseman who is said to have chased Ichabod Crane down over the bridge just a few yards away. The bridge, of course, is a modern traffic version, and the only real connection to the time is the Old Dutch Church and Churchyard up the hill.

362 Broadway, Sleepy Hollow, NY 1059

Old Dutch Church and Burying Ground and Sleepy Hollow Cemetery

“Indeed, certain of the most authentic historians of those parts, who have been careful in collecting and collating the floating facts concerning this spectre, allege that the body of the trooper, having been buried in the church-yard, the ghost rides forth to the scene of battle in nightly quest of his head; and that the rushing speed with which he sometimes passes along the Hollow, like a midnight blast, is owing to his being belated, and in a hurry to get back to the church-yard before daybreak.”

The Legend of Sleepy Hollow, 1820

Dating back to 1685, the Old Dutch Church would have served the people of Philipsburg Manor and its tenant farmers and slaves. It is also the resting place of the Headless Horseman. Measuring just two and a half acres, the burying ground almost melds into the sprawling adjoining 90-acre Sleepy Hollow Cemetery, where Washington Irving is buried. Other famous internees include Brooke and Vincent Astor, Major Edward Bowes, Andrew Carnegie, and Walter Chrysler.

430 North Broadway, Sleepy Hollow, NY 10591, 914-631-4497. http://sleepyhollowcemetery.org/events/tours-and-events/

The Philipsburg Manor and Kykuit

The Philipsburg Manor (also known as the Philipse Manor) is an open-air farm that incorporates original estate buildings like a watermill, barns, a manor house, and outbuildings. Frederick Philipse I, a Dutch settler, made a three-way purchase of a huge parcel of land north of Yonkers from Adriaen van der Donck, adding extra land from the Tappan tribe for an incredible 52,000 acres (21,000 ha) estate.

His land was tended by tenant farmers and slaves, with the slaves constructing the current buildings. His family’s fortunes were lost when the third and final lord, Frederick Philipse the Third was detained for treasonous acts by the American revolutionaries. The estate was auctioned off in parcels, with the funds raised going to the war coffers.

The centerpiece of Philipsburg Manor is a working gristmill. Set on the Pocantico River, the waterwheel still turns ancient millstones and actors will demonstrate how the grain is crushed. The main manor is styled to its 1750 form when the lord was managing imports and exports from under its roof.

The garden at the back is stunning, with herbs, vegetables, and beautiful seasonal blooms. In the barn, Ginger, the barn cat holds court, accepting pats from visitors learning about the role of the barn in keeping the manor in good stead during the freezing winter months.

Today, the museum stands, mainly due to the philanthropic efforts of John D. Rockefeller Jnr, who funded its restoration. His sprawling 40-room mansion, Kykuit is managed by the same body, Historic Hudson Valley – and you can purchase tickets to it from the Philipsburg Manor visitor center.

While the museum is currently mothballed due to the global health situation when in full operations, it’s brought to life by costumed actors who play the role of early traders, artisans, and estate workers. Also check out the gift shop for an excellent array of regional crafts, delicacies, and history books.

381 N Broadway, Sleepy Hollow, NY 10591

Adult: $12
Senior (65+): $10
Student (18-25): $10
Child (3-17): $6
Members + Children under 3: FREE

$2/ticket surcharge for onsite and phone purchases

Where to eat

The Bridgeview Tavern is to the north of Tarrytown. It’s a cozy pub with an eclectic menu of pub fare with a twist. For example, you can order shrimp and grits, Banh Mi, or even Belgian curried mussels.

http://bridgeviewtavern.com/

While Sleepy Hollow dominates the Halloween to-do list, don’t forget to experience the Haunted Hayride or the Great Jack o’ Lantern Blaze at nearby Croton on Hudson.

Looking for more vacation and road trip ideas across the northeast of the United States? We have great ideas across New York State, Vermont, Massachusetts, Rhode Island, New Hampshire, and Maine.

WHAT?

Formerly North Tarrytown, there’s plenty of things to do in Sleepy Hollow, the haunted hamlet of historic buildings and a sprawling cemetery.

WHERE?

Sleepy Hollow is a couple of minutes drive from Tarrytown in New York’s West Chester County.

HOW?

To get to Sleepy Hollow, the best way is to drive, though you can take an MTA train to

Philipse Manor and walk the ten minutes to Sleepy Hollow’s main attractions.