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Everyone knows the legend: a school teacher terrorized by the pumpkin wielding, horse-riding, terrifyingly scary Headless Horseman all set against the backdrop of eerily spooky Sleepy Hollow, a town full of myth and lore.
This tale has been entertaining audiences since 1820, when author Washington Irving while on a European tour crafted this story of fear and intrigue. As years became decades became centuries, this American legend has brought millions of visitors to see Sleepy Hollow and Tarrytown for themselves. Tourists travel the cobblestone streets and wander through the cemeteries to immerse themselves in the tale, and perhaps catch a glimpse of the Headless Horseman himself.
The Headless Horseman Bridge
(Photo: Sleepy Hollow Cemetery Historic Fund)
While navigating the wild wood of Sleepy Hollow, venture towards the infamous bridge where Ichabod crane *almost* reached safety before the Horseman threw his head and caused Crane to mysteriously vanish.
Located on Broadway, the bridge is close to the Sleepy Hollow Cemetery and the Headless Horseman Statue. Throughout the years, the bridge has rotted away and has been rebuilt in a similar fashion, sitting as a timeless piece with a portal to the past. If seeking out the Horseman, this spot would be a good starting point, especially on a foggy night.
Van Tassel Homestead
(Photo: Sleepy Hollow Cemetery Historic Fund)
This homestead is the location heavily inspired by the last place anyone (other than the Horseman) saw the skittish school teacher and where the Van Tassel family lived. Katrina Van Tassel, of course being the woman that Crane sought after. The house has been transformed throughout the years, becoming a tavern that Irving himself frequented, then a school and now a condominium.
While you can’t see the story unfolding physically in front of you, this homestead provided a pivotal part of the myth we’re all familiar with.
Headless Horseman Statue
(Photo: Sleepy Hollow Cemetery Historic Fund)
To culminate your tour of the town, finishing off the adventure at the Statue of the Headless Horseman will finally give you the glimpse you may be looking for. 18-feet tall and made of steel, this imposing statue gives you a moment frozen in fiction as it depicts our central antagonist chasing Ichabod Crane with his jack-o-lantern head in hand. This statue has been up since 2006, giving its visitors the photo op that they always wanted while exploring this sleepy town.
Planning your visit to this town of Legends & Lore? Shop our Fall Collection or harness the legend in style with our Pumpkin Head Tee