Headless Horseman Bridge

Sleepy Hollow bridge

This black-and-white photo is purportedly the Sleepy Hollow bridge of the mid nineteenth century.

Unfortunately, the bridge where Ichabod Crane was unseated by a pumpkin is the most popular destination in Sleepy Hollow that doesn’t exist—at least, not in the form and location in which it appeared in Washington Irving’s short story The Legend of Sleepy Hollow. 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 and reconfigured by New York State in the 1930s.

The Place Names of Historic Sleepy Hollow & Tarrytown

If 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. Irving notes in “The Legend” that the route of the Albany post road was once on the east side of the Old Dutch Church (now it runs on the west side), placing Ichabod’s collision inside what is today 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. It is on cemetery road Sleepy Hollow Avenue about 0.3 mile inside the cemetery’s south gate. Further upstream in Rockefeller State Park Preserve are several more rustic bridges.

A word about the depiction of the bridge on film. Although Walt Disney and Tim Burton dressed up their versions of Sleepy Hollow with covered bridges, there is no evidence in either Irving’s story or historical records that Sleepy Hollow’s bridge ever had a roof. Covered bridges were used further up the Hudson Valley, always to span rivers much broader and deeper than our little creek.

“The bridge became more than ever an object of superstitious awe, and that may be the reason why the road has been altered of late years, so as to approach the church by the border of the mill-pond.” -The Legend of Sleepy Hollow