Headless Horseman Bridge — Attraction in Town of Mount Pleasant

If you know the Legend of Sleepy Hollow then you know the bridge, or maybe you think you know the bridge. The problem with movies is they alter the collective imagination far more than any other medium, and well the bridge that Washington Irving knew when he wrote the legend looks nothing like what has been depicted. The original bridge was a wooden truss bridge, not a covered bridge, and based on an old survey of the town was roughly 600 feet upstream of the current bridge. The Old Post Road used to wrap around the church, head back north before turning to cross the river. Some have suggested the original bridge aligned with Holland Ave, but I think it was further than that, more in line with Gordon Ave today, and possibly as far as Tappan Ave and New Broadway. That original bridge has long since disappeared.

Three later maps from 1867, 1872, and 1881 all still draw an old road and suggest a bridge upstream from the new road alignment close to what we see today. This section of the river however has been reworked many times over the centuries with mills, dams, and factories of various sorts being constructed. It is said nothing remains from the true first bridge, not even the abutments, and that very well may be true. My best guess would put it at roughly 41° 5'28.59"N 73°51'37.69"W.

By the 1850s the aqueduct had come through town and this resulted in the realignment of many of the streets close to how we see them today. At this point Kingsland funded the construction of a stone arch bridge close to the bridge we have today. The Old Post Road took a straighter course as it passed the church and crossed the river. That bridge was a massive single arch stone design and Broadway was aligned a bit upstream of where it is today. This is likely the reason Old Broadway is shifted slightly to the east.

By the 1900s the abutments had settled leading to some cracks opening in the structure. This was the motivation for the third generation bridge to be constructed. The Old Post Road was again straightened a bit more though not quite to what we see today. In 1912 construction began on the concrete arch bridge faced with stone, funded by William Rockefeller. The road was widened in the 1930s and it was at this point that the final realignment of the Post Road occurred, leaving us with the bridge we see today.

While this bridge serves the same purpose of the original bridge that sat at the heart of Washington Irving’s legend, it is far removed both in location and character of that original span. A simple wooden truss crossing the Pocantico River aligned with the north end of the Old Dutch Burying Ground, that was the structure that stopped the horseman, not a 120 foot wide concrete arch behemoth. However, this bridge is not meant to be a recreation, but rather to honor the author that put this little sleepy...

Not sure why all the guides saying this was cool. Barely looks like a bridge, you could pass by and miss it if it weren't for the sign. Look at all the pics posted...its mostly the sign. The town really dropped the ball when building this modern "bridge". If you're in the area I guess its ok the check out but DO NOT make a special trip for...

The cemetery was very cool but the bridge was a small little thing. Disappointing. the legend is really exaggerated. That being said, sleepy hollow is a really cool town. Very beautiful. It's right next to Tarrytown so you can visit both towns in the same day. In late October and early November the trees are just beautiful with the...