Headless Horseman Bridge

Washington Irving certainly put Sleepy Hollow on the map with his 1820 Gothic horror story, The Legend of Sleepy Hollow. In it, the gloomy town is said to be haunted by the ghost of a Hessian soldier in search of his head, which he’s said to have lost to a cannonball while fighting in the American Revolution. While the story may evoke more fear than intrigue in the small town, it is of course completely fictional (and in fact a rather charming town). The bridge that sets the story’s climax, however, is very much real. 

After the protagonist Ichabod Crane leads the Headless Horseman on a horseback chase through the woods in the dark of night, he’s finally caught at the foot of a wooden bridge that stretches over the Pocantico River (in many folktales, bridges symbolize a liminal space between the realms of the living and the dead). The Headless Horseman hurls a pumpkin at Crane, striking him in the head and leaving him to an unclear fate. Come morning, all that’s found are Crane’s trampled saddle and broken chunks of pumpkin.

At the time of its writing, there was an actual wooden bridge at the site of Crane’s fictional gourd attack. While it was replaced by a more modern, concrete iteration in 1912 by William Rockerfeller, the structure is still known as “The Headless Horseman Bridge.” You can walk across it or have someone chase you for the real Crane experience—just look out for pumpkins.