75 Unique Destinations
For Business & Pleasure,
With More on the Way

Engaging Getaways and Venues for:

  • Outdoors, History, and Food Enthusiasts
  • Meetings, Retreats, Weddings, Reunions

Click above to like this destination.

USA/Mid-Atlantic: Pocantico Hills and Sleepy Hollow, NY

The Home of Ichabod Crane


The Highlights: Stunning Hudson River views, colonial footpaths in legend-filled forests, the remains of a large riverside estate.

Places to Visit: An 17th-Century farmstead; Kykuit, home of the Rockefellers; the Old Dutch Church and old graveyard where Washington Irving is buried.

Meetings & Event Options: Hotels in nearby Tarrytown and other Westchester towns and cities provide many options. Historic homes and estates along the Hudson River can also be rented for unique, memorable events.

Sleepy Hollow

We can only imagine the rigors faced by the early Europeans who first settled the Hudson River Valley. After the stress of a long ocean voyage and the prospect of setting up a new life, they encountered a vast, virgin wilderness with strangely clothed inhabitants. The new world undoubtedly played on the minds of these travelers, whose first explanation for the strange phenomena they encountered often included some aspect of the supernatural.

As 19th-Century author Washington Irving tells us in his books, the early Dutch settlers who settled the Hudson River lands you travel on during this walking tour had particularly vivid imaginations, especially if you have a taste for the macabre. Irving passed through the Hudson River Valley in his youth and fell in love with its charms. Years later, while living in London, he wrote his famous The Legend of Sleepy Hollow, borrowing, it is said, from stories he heard while visiting a friend on an estate near Kinderhook in the Hudson Valley. One literary historian, however, has attributed much of Irving’s legends to German tales the author read while living in London.

In either case, the visitor to Sleepy Hollow should have little trouble imagining the valley in Irving’s time, because the land covered by this walk still maintains its quiet, rural character and has some of the same footpaths that were in use during Irving’s time.

Pillipsburg Manor

The area known as Sleepy Hollow that is covered by this walk was first inhabited by Native Americans, part of the Weckquaesgeek and Sintsinct tribes. The tribes spent summers on the Hudson River shore enjoying its plentiful harvest of oysters, before moving inland during winter to sheltered valleys away from the wind.

The first white settlers came to the area in the 1600s, after the voyage of Henry Hudson up the river. Although the Dutch West India Company offered generous incentives to attract settlers from Holland, including near-feudal powers for people with sufficient resources, few people took the bait, and settlement remained sparse throughout most of that century. The lack of competition made it possible for a penniless Dutch carpenter, who eventually changed his name to Frederick Philipse, to amass an extraordinary domain covering almost half of present-day Westchester County.

In the late 17th Century, he established a grist mill at the mouth of the Pocantico River, where river sloops could find harbor and transport animal pelts, grain, and other agricultural products down to New Amsterdam, which later became New York City. Early maps show that a number of tenant farmers rented land from Philipse in the area of the walk, so the fields and forests you cover probably have not changed much from that time. Gone are the few farmhouses that dotted the area, but some of the old farm roads remain.

If the legends of these early settlers are true, you may have one of several supernatural encounters along your walk. When you’re on the hilltop on a misty evening near the walk’s Waypoint 15, perhaps you’ll catch sight of the Flying Dutchman, the specter of a ship said to sail silently up river in defiance of wind or tides, with a Dutch flag flying from its mast. Or you may see the ghost of a young Dutch partygoer named Van Dam on the river in a rowboat hopelessly looking for shore. Against the advice of his friends, he had headed home from a party drunk at midnight on the Sabbath and was never seen again.

Rockwood Hall State Park

If you walk along the trail near Spook Rock, perhaps you’ll see strange lights produced by the ghost of a Native American who comes in search of her lost husband and baby. The men who built the Old Croton Aqueduct, which you pass on the walk, were terrorized by ghosts they said haunted the Pocantico River Valley near their camp.

As you walk along the river, you may be overcome by an unexplained drowsiness, if the stories of Washington Irving are true. It’s the result of a spell cast by a Native American wizard to subdue an enemy tribe, and it explains why the valley here is called Sleepy Hollow.

Of course, Sleepy Hollow’s most famous legend is the story of Ichabod Crane, who disappeared on his way home from a party late at night after encountering the Headless Horseman on a dark wooded trail. A setting much like the one described by Washington Irving can be found on Gorey Brook Road, one of the oldest roads in the area and just a few hundred yards from where Irving imagined Ichabod Crane made his fateful encounter. The setting probably has changed little in hundreds of years.

All of this magical land would have fallen into the hands of suburban developers, if not for the Rockefeller family, which began buying land here in the 1890s. Over the years, they created a vast preserve of manicured meadows and forests, crisscrossed with an impressive network of bridle paths. John D. Rockefeller built a great mansion he called Kykuit, which you can visit today, and his brother William constructed an impressive mansion called Rockwood Hall, which stood on sweeping grounds facing Hudson Rover. All that remains of this mansion are the foundations and beautiful grounds, now open to the public. There is not a prettier park along the Hudson River in southern Westchester, and its entrance is at the western end of Route 117, only a short drive from the main entrance to Rockefeller State Park.

Share | |
Subscribe to Digital/Print Editions

ExperientialView our digital downloads

Subscribe Today for Free


Pulse Experiential Travel

Kiawah Island Golf Resort