New England is rife with gothic history to draw on for a D&D campaign; Sleepy Hollow is a great place to start.
The Legend of Sleepy Hollow
The Sleepy Hollow we know today is a recent invention; it was originally North Tarrytown in the late 19th century, adopting its current name in 1996, and for good reason: Sleepy Hollow achieved international fame thanks to Washington Irving’s “The Legend of Sleepy Hollow“, an 1820 short story about the Headless Horseman. Irving lived in Tarrytown and is buried in Sleepy Hollow Cemetery.
Not surprisingly, Sleepy Hollow’s reputation makes it something of a Halloween icon. It’s considered one of the most haunted places in the world. And that makes it perfect for fantasy and horror tabletop gaming inspiration.
The Headless Horseman
“The Legend of Sleepy Hollow” and its eponymous specter was made famous by one of the short stories in Irving’s The Sketch Book of Geoffrey Crayon, Gent. (Irving used the pseudonym Geoffrey Crayon). Irving wrote the book while traveling Europe, and it’s not a surprise that the headless ghost has its root in European legends, particularly the dullahan.
The myth may have been inspired by the corpse of a Hessian jager found by the Van Tassel family and later buried in an unmarked grave in the Old Dutch Burying Ground. This is the loose plot outline of Tim Burton’s Sleepy Hollow, which manages to combine Edgar Allen Poe’s love of ratiocination and his chief investigator C. Auguste Dupin with the superstitious schoolmaster of Ichabod Crane.
In the story, it’s implied the Headless Horseman is a prank played by Abraham Van Brunt to just drive off Ichabod as a rival for Katrina Van Tassel’s hand. The movie goes much further, including both the prank and a secret plot to use the fiendish horseman as an assassin, controlled by whomever holds his head.
There are plenty of ways the Headless Horseman has been statted (I tried as well with 5E Foes: Celtic Bestiary, the dullahan entry), but the official version for Dungeons & Dragons features in Van Richten’s Guide to Ravenloft.
Rip Van Winkle
The Sleepy Hollow TV series took a different, but related, approach. Ichabod Crane is a spy working for George Washington as a double agent. He beheads a horseman, only to awaken in 2013 in Sleepy Hollow, with Washington’s Bible in hand. He faces off against the Horseman in this new timeline, who he later learns is an avatar of Death, under the service of the fiendish Moloch. The show combined elements of the Irving’s short story with another story he made famous, “Rip Van Winkle.”
By the time the show reached its fourth season, it had given up on its Sleepy Hollow setting altogether (which was only loosely based on the actual town). The finale involved the Philosopher’s Stone, Lucifer, and the Four Horsemen of the Apocalypse.
While the show may have sputtered (and ended prematurely, with Crane never quite resolving his own plot), the idea of combining time travel shenanigans while transforming the Headless Horseman into one of the Four Horseman of the Apocalypse can certainly be mined for ideas in a fantasy or horror campaign.
The Real Legend
Sleepy Hollow is far weirder than the movie or series that portrayed it. Here’s a quote describing the web site, Sleepy Hollow Country:
We’ve got haunted taverns, houses and even a church. Ghosts, spectres, a mysterious woman clad all in black, a woman dressed all in white wailing atop a cliff. Pirates and highway men. Ghost ships on the Hudson River, a Dutch goblin king living atop a local mountain. Unsolved murders. UFOs. Exploding mosquitoes. Yep, we’ve even had a plague of exploding mosquitoes.
The Dutch goblin king is referenced in Irving’s short story, “The Storm-Ship” which helped make Bannerman Castle famous. The goblin leads a crew of imps, capable of controlling the winds and invoking storms. Shrink a genie down to size or reskin a bone devil for the same effect, with an army of imps to boot.
The exploding mosquitoes were inspired by the arrival of gasoline, heavily implying that reliance on the fuel (or was it alcohol?) was causing mosquitoes — drawn to open flames — to explode. Oil-drinking stirges could pose a similar threat.
And then there’s Hulda, a heroine spun from myth whose magical capabilities have only expanded in the retelling. She now has her own headstone, though there’s little evidence she was a real person. Hulda’s been credited with everything from herbal healing powers, to stealthily bequeathing gifts of food to her starving neighbors, to taking up arms against British soldiers during the Revolutionary War. She’d make a great character or NPC for any game as a highly capable ranger.
Sleepy Hollow, like much of its mythology, is spun from just enough truth to make it believable. The town itself has capitalized on its reputation, and visiting it during Halloween is an experience. Just be ready to walk everywhere, because the influx of tourists snarls traffic for hours.
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