Sleepy Hollow Country

Editor’s note: This article overlaps information I compiled for the Sleepy Hollow Cemetery and Friends of the Old Dutch Burying Ground web sites.
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Identifying landmarks from “The Legend of Sleepy Hollow” has long been popular among visitors to Sleepy Hollow Country. In spite of 200 years of growth that transformed this sleepy farming community into a modern suburb, most major landmarks from the story still exist in some form. Alas, the bridge upon which Ichabod Crane lost his race with the Headless Horseman and the Sleepy Hollow schoolhouse have been lost to the ravages of time and the elements.

If you don’t mind a little walking, you can easily trace Ichabod’s famous ride up the Albany Post Road (now US Route 9; named Broadway in Tarrytown and Sleepy Hollow). From the site of the Elizabeth Van Tassel house, walk north about 0.3 mile on Route 9 (North Broadway) to the André captors’ monument in Patriots Park, the spot where Ichabod was met by the headless horseman. From here you can, if you wish, approximate Ichabod’s flight by galloping frantically along Broadway until you reach the Old Dutch Church, about 0.6 mile.

The Van Tassell Homestead. Popular tradition attaches the coquettish Katrina to the Elizabeth Van Tassel house, a tavern before and during the Revolutionary War. Historian Edgar Mayhew Bacon, in his 1898 book Chronicles of Tarrytown and Sleepy Hollow notes that Irving was a frequent visitor at this old house “especially during the time that his [Irving's] sister boarded there with the Mott family.” In their 1975 History of the Tarrytowns, Jeff Canning and Wally Buxton concur, adding that the house was once part of the 165 acre John Van Tassel farm. The former Elizabeth Van Tassel house was located at what is now the northeast corner of Hamilton Place and North Broadway in Tarrytown. The Landmark Condominium building presently on the site was formerly the Frank R. Pierson School (ca. 1897), which itself was formerly the Washington Irving High School until the 1920s when the school district built a new Washington Irving High School at the corner of Franklin Street and South Broadway in Tarrytown. There is a bronze marker on the southwest corner of the Landmark noting that it occupies the site of the former Mott Tavern. Landmark Condominium, 18 North Broadway (1 block north of Main Street), Tarrytown, NY 10591

Patriots Park and the André Captors’ monument. The marshy area where Ichabod first encountered the headless horseman has long since been drained, but its stream still flows through a park shared by the villages of Tarrytown and Sleepy Hollow. A monument marks the spot where, on September 23, 1780, John Paulding, David Williams, and Isaac Van Wart captured British spy John André and exposed Benedict Arnold’s treasonous attempt to turn over West Point to the British. At that same location Ichabod, too, met a fateful sentry. André’s tree, the ancient tulip tree under which the spy was captured, no longer stands.

“About two hundred yards from the tree a small brook crossed the road, and ran into a marshy and thickly-wooded glen, known by the name of Wiley’s Swamp. A few rough logs, laid side by side, served for a bridge over this stream . . . It was at this identical spot that the unfortunate André was captured, and under the covert of those chestnuts and vines were the sturdy yeomen concealed who surprised him. . . .In the dark shadow of the grove, on the margin of the brook, [Ichabod] beheld something huge, misshapen and towering. It stirred not, but seemed gathered up in the gloom, like some gigantic monster ready to spring upon the traveler. . . He appeared to be a horseman of large dimensions, and mounted on a black horse of powerful frame. ” –The Legend of Sleepy Hollow

The millpond. The millpond where Ichabod Crane strolled with fair companions is intact and part of a living history museum where you can experience Sleepy Hollow’s agrarian past. It is a restoration of the 17th century Dutch manor that defined the economy of this area for generations. You may need to supply your own bevy of country damsels. Philipsburg Manor Upper Mills, 381 North Broadway, Sleepy Hollow, NY 10591.

“Our man of letters, therefore, was peculiarly happy in the smiles of all the country damsels. How he would figure among them in the church-yard . . . or sauntering, with a whole bevy of them, along the banks of the adjacent mill-pond; while the more bashful country bumpkins hung sheepishly back, envying his superior elegance and address.” –The Legend of Sleepy Hollow

Old Dutch Burying Ground and the Old Dutch Church of Sleepy Hollow. The burying ground in which the unfortunate Ichabod sought refuge is the yard of the Old Dutch Church, not the adjacent Sleepy Hollow Cemetery, which had not been established at the time Irving wrote “The Legend.” The burying ground is of course the purported haunt of a certain headless Hessian, but also the resting place of local citizens who likely inspired Irving’s characters of Katrina Van Tassel, Brom Bones, and others in “The Legend of Sleepy Hollow.” Purchase a copy of Tales of the Old Dutch Burying Ground from Sleepy Hollow Gifts Online or at the museum shop at Philipsburg Manor. A fold-out map at the center of the book guides you through the churchyard. Old Dutch Church and burying ground, 430 North Broadway (Route 9 across from Philipsburg Manor), Sleepy Hollow, NY, 10591.

The Headless Horseman Bridge (aka the Sleepy Hollow Bridge). Whatever wooden span crossed the Pocantico in the late 1700’s has long since rotted away. It’s successor is the 4-lane concrete and steel Route 9 (successor to the post road) bridge constructed by William Rockefeller in 1912. The blue-and-yellow state historic marker is at the south gate to Sleepy Hollow Cemetery, within sight of the Old Dutch Church. Read more about the bridge here.

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