The History Of Sleepy Hollow, NY

Sleepy Hollow is a town in lower Westchester County, NY. The local settlement by the Dutch and the local
history pre-dates the American Revolution by over 135 years. Members of this community played an
important role during the Revolution and in the development of Westchester County and New York State.

In the year of the Half Moon, 1609, the two square miles that make up the Village of Sleepy Hollow belonged
to the larger domain of the Weckquaesgeck Indians. This Native American tribe is variously described as a
Delaware Tribe or a Mohican Tribe, or perhaps some mix of the two. During the early days of New
Netherlands, relations been this tribe and the Dutch were relatively peaceful, but by 1643 the Dutch were at
war with the Weckquaesgecks and several other tribes of the region. Exactly when Europeans first settled
in the Sleepy Hollow area is unclear.

The legends of Sleepy Hollow span the centuries from Native American times to the present. The names of
the famous and the infamous, both historic and legendary, have all left their mark on this quiet Hudson
River village 25 miles north of Manhattan. Defying the passage of time, this magical area has managed to
preserve much of the history and natural beauty which have always drawn people to it.

Some sites in this town include:

The Old Dutch Church of Sleepy Hollow (a national historic landmark)
The Old Dutch Burying Ground
Sleepy Hollow: Valley of Legends
The Sleepy Hollow Bridge (The Headless Horseman Bridge)
Philipsburg Manor: 18th Century Restoration
Ichabod’s Flight: Backdrop to the legend
Kykuit: The Rockefeller Family Estate
Washington Irving’s Grave
The 1883 Lighthouse
Captain Kidd’s Rock
The John C. “the pathfinder” Fremont House
The Croton Aqueduct Trail
The Rockefeller State Park Preserve

This town became a household name after the “legend of sleepy hollow” written by Washington Irving, and
later the Tim Burton movie “sleepy hollow” starring Johnny Depp and Christina Ricci

some key towns people buried in the Old Dutch Burial Ground
Frederick Philipse (1626-1702) – early settler, founder of the Old Dutch Church in Tarrytown, and builder of
Philipse Manor
Eleanor Van Tassel Brush (1763-1861) (model for Katrina in The Legend of Sleepy Hollow)
Joseph Youngs (1722-1789) and Susannah Youngs, (1732-1783) were the parents of Samuel Youngs (model
for Ichabod Crane). Samuel Youngs was originally buried there but his remains have been removed to
Ossining’s Dale Cemetery
Abraham Martling (1743-1830), inspiration for Brom Bones


Sunnyside : Former home of Washington Irving is reportedly haunted by his ghost and those of his nieces
who used to take care of the place. He likes to pinch women, and the nieces have been known to tidy the
place at night after the interpreters have left for the evening. Located in nearby Irvington

Patriot’s Park: Patriot’s park is a small, quiet spot juxtaposed between the two villages of Sleepy Hollow
and Tarrytown. The infamous Major Andre was captured, and later executed by American Patriots in or near
this park during the American Revolution. He is said to haunt the park. Patriots Park is where Ichabod Crane
first saw the Headless Horseman.

Sparta Cemetery is said to be haunted by a number of spirits unknown as of this date. People have
reported inexplicable mists and voices late at night in the fall at or around this old cemetery.
others have claimed to have seen the headless horseman riding through the Sleepy Hollow Cemetery
(other than on Halloween night during the haunted hay ride).

The cemetery covers about 100 acres, and has over forty thousand burials within its grounds including
Leo Baekeland (1863-1944) – the father of plastic: Bakelite is named for him. The murder of his grandson’s
wife Barbara by his great-grandson, Tony, is told in the book Savage Grace
Major Edward Bowes (1874-1946) – early radio star, he hosted an “Amateur Hour”
Andrew Carnegie (1835 – 1919) – businessman and philanthropist
Walter Chrysler (1875-1940) – businessman, commissioned the Chrysler Building
Samuel Gompers (1850-1924) – founder of the American Federation of Labor
Mark Hellinger (1903-1947) – film producer. The Mark Hellinger Theater in NYC is named after him

The legend of Rip Van Winkle takes place in Palenville, in southern Green County. It was written by
Washington Irving. The legend says that Rip Van Winkle took a twenty year nap at Sleepy Hollow after
drinking liquor that was given to him by some supposed followers of Henry Hudson. When he woke up he
went back to his town of “Laughing Water” and found many changes. One good change that he found was
his wife was dead. He was glad of this because she was a thorn in his easy going life.

Another legend involves a famous pirate named Captain Kidd who at one time landed in Sleepy Hollow. He
supposedly sailed up the Hudson River as far as the Catskills in search of a place to hide his Spanish bride
from a vengeful rival. Unfortunately, she was found by the rival and carried to Leeds where she was
imprisoned, persecuted, and finally killed. Residents now say that her ghost is pulled through the streets by
ghostly horses at midnight

According to Temple and Sheldon (1875), Captain Kidd and his men ascended the Connecticut River
searching for a place to bury a treasure of gold, somewhere secluded but distinctive. They buried the chest
of gold and drew lots to see which of their number would be killed so that his body could be left on top of
the chest to protect it from all treasure hunters. Over the years a legend grew up around the treasure – the
gold could be dug up only by three people at midnight when the full moon was directly overhead. They must
form a triangle around the exact spot and work in absolute silence, words would break the charm!
In the early 19th century, Abner Field and two of his friends attempted to find the treasure by following the
directions exactly. At midnight, under a full moon shining directly on them, they sweated and dug, silently.
Shovelful by shovelful, they dug deeper and deeper. The sweat poured off their bodies even in the chill
night air. The mosquitoes swarmed around, biting, but the three men were afraid to kill them for fear the
sound would break the charm. Any amount of discomfort could be tolerated in order to find the buried
treasure chest. Suddenly there was the echoing sound of crow-bar striking against iron. Just as the men
saw a corner of the chest emerge from the dirt, someone exclaimed,”You’ve hit it!” and the trio of treasure
hunters watched in consternation as the chest immediately began to sink out of reach.