The Truth Behind the Legend of Sleepy Hollow


The line between historic fact and fiction, or folklore, often becomes blurred as stories are passed down from earlier generations.

Linked forever to Halloween, The Legend of Sleepy Hollow is a famous story by Washington Irving that touches on the culture and many of the traditions of the Dutch who inhabited New York’s Hudson Valley. The names of the characters depicted in the story, along with their personalities, are composites of actual people and families known to Irving. Some of the names, including that of Katrina Van Tassel, can be found today on the tombstones in the churchyard of the Old Dutch Church in Sleepy Hollow. The church, the Revolutionary War and the stories about the Dutch residents of the area all are part of Irving’s story.

Frederick Philipse, lord of Philipsburg Manor, built the church during the late 1600s. The surrounding cemetery grew over the years and now contains 1,743 tombstones. That number, however, only approximates the number of people who have been interred there over 300 years. Some stones contain more than one name and the oldest markers, made from wood, are long gone. Very little is known about the early burials, and, according to the records of Historic Hudson Valley, the only record about the first internment in this ground is that it occurred “on the knoll above the river.”

The burying ground started as the town cemetery. Some available space remains but it won’t be used for future internments since historians believe burials in this area already could be five layers deep. Legend has it that the earliest burials were relocated when the church was built. In addition to the several thousand resting outside the church, a crypt in the church has about 20 internments that include Philipse, two wives, two sons who never married and his other children.

The cemetery’s residents include the military secretary for General Ulysses S. Grant, the drummer boy for General Philip Henry Sheridan and William Paulding, a mayor of New York City during the early 1800s. Also at rest here is “Hedda the Witch.” Her last name is not known and since she was branded a witch, though many believed she was a good witch, a headstone could not be placed on her grave. Her approximate resting place was marked with a nondescript fieldstone. A number of years ago, a small plaque referencing her was added to that stone.

Who Was Ichabod Crane?

The real Ichabod Crane was a gunnery officer who served with Irving during the War of 1812. Irving, however, fashioned the character of his Ichabod Crane after a school teacher named Jesse Merwin from Kinderhook, New York. Merwin had hired Irving to tutor the sons and daughters of politicians.

Don’t look for Crane’s tombstone in the cemetery. Though he sang in the church choir, he was buried in a family plot on Staten Island.

Brom Bones is a composite of two people acquainted with Irving – Abraham Martling was the village blacksmith and his son, also named Abraham, was the village cobbler. It is believed the name “Brom” was derived from “Abraham” and that “Bones” was borrowed from the blacksmith who used it as a nickname for his skinny son.

Headless Horseman Was German Soldier

The Headless Horseman is a character based on a Hessian soldier, one of the many mercenaries hired by King George to fight Americans during the Revolutionary War. This soldier is believed to have been decapitated by a cannon ball during the nearby Battle of White Plains. (The land surrounding the church also was the scene of a skirmish during the war.)

A member (Elizabeth) of the large Van Tassel family that inhabited the area during the war, is credited with giving the headless soldier a proper burial in the Old Dutch Burying Ground to repay kindness from another Hessian soldier who saved her baby from a burning building. The homes of many area residents, including a number of them that belonged to the Van Tassel clan, were burned during the war.

Though it could be a stretch that an unknown dead enemy soldier would have been transported about 10 miles from White Plains rather than buried on or near that battlefield, Irving learned about this story and the internment in the churchyard from the church sexton. Historians believe the solider is there, but exactly where is not possible to determine due to the multiple layers of graves.

The Old Dutch Church is located across a main road from the original Philipsburg Manor house. The area is a popular tourist attraction year round, but especially during October. While some of the nearby roads have been widened or added over time, it is possible to shed the modern world and imagine the activity in this area before and during the Revolution, and during the time when Irving fashioned his story.