The Headless Horseman Bridge

Sleepy Hollow Bridge

Undated photo of purported Sleepy Hollow bridge.

We often get requests for directions to the bridge from Washington Irving’s short story “The Legend of Sleepy Hollow.” Unfortunately, the bridge where Ichabod was unseated by a pumpkin is the most popular destination in Sleepy Hollow that doesn’t exist—at least, not in its original form and original location. Whatever simple wooden span crossed the Pocantico River in the late 1700’s has long since rotted away. In fact, Sleepy Hollow village historian Henry Steiner has documented at least five distinct bridges that carried the Albany Post Road over the stream. Scarcely a trace remains of any except the most recent, the 4-lane concrete and steel U.S. Route 9 (the modern successor to the colonial-era Albany Post Road) bridge constructed by William Rockefeller in 1912.

placenamesIf you’ve got the inclination, pick up a copy of Steiner’s The Place Names of Historic Sleepy Hollow & Tarrytown and venture off in search of the footings of one of the earlier bridges. Faint traces are said to be found inside what is now Sleepy Hollow Cemetery. If you strike out, the cemetery’s own bridge, upstream from where the post road bridge stood in Washington Irving’s time, is rustic enough to make a dandy souvenir photo.