“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
Unfortunately, the Sleepy Hollow 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".
The simple wooden span that 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. Even that was heavily modified in the 1930s when New York State reconfigured the route of the road.
For a more comprehensive history of the Headless Horseman Bridge, see this article by Jim Logan, Superintendent of Sleepy Hollow Cemetery.
The Cemetery Bridge
In “The Legend”, Irving describes the route of the Albany post road 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. The cemetery’s own bridge, upstream from where the Post Road bridge stood in Washington Irving’s time, is rustic enough for a selfie. It is on cemetery road Sleepy Hollow Avenue about 0.3 mile inside the cemetery’s south gate. Be respectful, the cemetery bridge is used daily by funerals and mourners visiting graves.
Further upstream in Rockefeller State Park Preserve are several more rustic bridges.
The Covered Bridge
A word about the depiction of the bridge on film. While 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 broader and deeper than our little creek.