Nothing says Halloween in Sleepy Hollow like a visit to the haunts of the headless horseman. Several major landmarks from the story and the entire route of Ichabod Crane’s flight from the horseman are easily identifiable: the location of the Van Tassel homestead, the spot where British spy John André was captured, the millpond at Philipsburg Manor, the Old Dutch Church, Raven Rock, and the secluded valley Washington Irving called Sleepy Hollow. Ichabod Crane’s schoolhouse and the bridge upon which he lost his race with the Headless Horseman have been lost to the ravages of time. You can read the full Legend here and buy a copy here.
Van Tassel homestead
Schoolmaster Ichabod Crane began his famous flight from the headless horseman at the home of the Van Tassel family.
Local tradition attaches the flirty Katrina to the Elizabeth Van Tassel house, which was converted to a tavern before the Revolutionary War by the Mott family. 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 agree, adding that the house was once part of a 165 acre farm owned by John Van Tassel.
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, three local militiamen captured British spy John André, exposing American general Benedict Arnold’s treasonous plan to turn over the fortifications at West Point to the British. Since Arnold’s plan also involved handing over George Washington, the three locals may have averted a very different ending to the American Revolution. In The Legend, this spot is haunted by the ghost of the ill-fated André (the spy was hanged at Tappan, NY across the Hudson River) and is where the headless horseman begins trailing Ichabod.
The park and monument are located on the west side of Route 9 (Broadway) at the border between Sleepy Hollow and Tarrytown.
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 manor house and mill are restorations of the 17th century Dutch manor beside whose millpond Ichabod Crane strolled with the local girls. Country damsels are in shorter supply in these parts than in Ichabod’s day, so you may need to supply your own. Frederick Philipse, builder of the mill and manor house, also constructed the Old Dutch Church of Sleepy Hollow.
Philipsburg Manor, 381 North Broadway, Sleepy Hollow, NY 10591, 914-366-6900
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 Church
Ichabod Crane’s flight from the headless horseman ends at the bridge leading into the yard of the Old Dutch Church. The 3-acre burying ground around the church is the purported final resting of local citizens who likely inspired Irving’s characters of Katrina Van Tassel, Brom Bones, and others in “The Legend of Sleepy Hollow,” and also of the horseman himself.
The church and churchyard are adjacent to but not affiliated with the 90-acre Sleepy Hollow Cemetery.
Old Dutch Church of Sleepy Hollow and Old Dutch Burying Ground, 430 North Broadway, Sleepy Hollow, NY, at the south gate to 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
Nestled in a far corner of the Rockefeller estate is a rock configuration known as Raven Rock. Local historians Jeff Canning and Wally Buxton describe three ghostly associations with this spot in their book History of the Tarrytowns. It is far enough off the beaten path that its location has remained obscure even for most locals. Until, that is, archivist Lucas Buresch did a little sleuthing that made a positive ID on the rock formation of Raven Rock. The rock and one of its legendary ghosts make an appearance in “The Legend of Sleepy Hollow:”
Several of the Sleepy Hollow people were present at Van Tassel’s, and, as usual, were doling out their wild and wonderful legends. Many dismal tales were told about funeral trains, and mourning cries and wailings heard and seen about the great tree where the unfortunate Major André was taken, and which stood in the neighborhood. Some mention was made also of the woman in white, that haunted the dark glen at Raven Rock, and was often heard to shriek on winter nights before a storm, having perished there in the snow. -The Legend of Sleepy Hollow
The Real Sleepy Hollow
The Sleepy Hollow of legend is the valley of the Pocantico River, a small stream that flows into the Hudson River. The valley and stream are remarkably accessible and sleepy to this day, flowing through Rockefeller State Park, Sleepy Hollow Cemetery, and the village of Sleepy Hollow’s Douglas Park. Roaming the endless carriage roads of the state park or wandering among the monuments of the cemetery it’s easy to conjure an image of Ichabod Crane making his way to his schoolhouse. In the gathering gloom of some overcast autumn afternoon, you might just hear hoofbeats approaching from behind. But don’t panic—the state park allows equestrian access to some trails. If you wish to make your own horseback ride through Sleepy Hollow, there is horse trailer parking at the park’s main entrance on Route 117.
Not far from this village, perhaps about two miles, there is a little valley or rather lap of land among high hills, which is one of the quietest places in the whole world. A small brook glides through it, with just murmur enough to lull one to repose; and the occasional whistle of a quail or tapping of a woodpecker is almost the only sound that ever breaks in upon the uniform tranquility.
I recollect that, when a stripling, my first exploit in squirrel-shooting was in a grove of tall walnut-trees that shades one side of the valley. I had wandered into it at noontime, when all nature is peculiarly quiet, and was startled by the roar of my own gun, as it broke the Sabbath stillness around and was prolonged and reverberated by the angry echoes. If ever I should wish for a retreat whither I might steal from the world and its distractions, and dream quietly away the remnant of a troubled life, I know of none more promising than this little valley.
From the listless repose of the place, and the peculiar character of its inhabitants, who are descendants from the original Dutch settlers, this sequestered glen has long been known by the name of SLEEPY HOLLOW…-The Legend of Sleepy Hollow
J.W. Ocker of Odd Things I’ve Seen retraces Ichabod’s flight from the headless horseman: