RPG Evolution: Inspiration from Sleepy Hollow

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.

Other Sources of Inspiration​

As I travel on vacation I do my best to document the experience and how I might use it as inspiration for my games. Here's where I've been so far:

• Appalachian Trail
• Bari
• Corfu
• Dubrovnik
• Edinburgh
• Kotor
• Sleepy Hollow
• Venice
• Zakynthos

 

[Remathilis]

The 5e version went back to the Irish folk tales, rather than just the Washington Irving version. I vaguely remembered there was one in the 2nd edition Ravenloft box. Giving it a sickle seems like an odd choice, I don’t know where that comes from.

I guess they felt the sickle seems akin to a horseman's scythe?

 

[Voadam]

Giving it a sickle seems like an odd choice, I don’t know where that comes from.

I think they were just making it a bit their own distinctive version.

From his 2e Darklords entry:

Nearly every domain haunted by the Headless Horseman knows a different tale of his origin. In Falkovnia, some say the spirit was a victim of Drakov's men, wrongfully beheaded. In Barovia, they say he sliced off his own head rather than fall prey to one of Strahd's minions, who later gave the head to Strahd.
In Borca, folk have the most specific tale, which they are sure is most true. Borcans say the Horseman was once a bard who had the misfortune of meeting Ivana Boritsi, the lord of Borca. Ivana invited him to her private baths (an offer he could not refuse). Unfortunately, she was in a fickle mood, and he was unable to entertain her. Inspired by the sickle shape of the moon, she had him beheaded, continuing her bath in his blood.
The headless body, as the story continues, was cast into the river near Levkarest. (As to what Ivana did with the head, no one is sure.) The corpse floated downstream until it neared the road to Sturben, where it became lodged beneath a bridge. On the night of the next sickle moon, the body arose. Ravenloft's Dark Powers supplied it with a phantom steed and a crescent-shaped blade. Ever since that time, the Horseman has ridden forth to cleave the necks of unfortunate travelers.

 

[Clint_L]

I love the essential elements of the Sleepy Hollow story: an isolated community, haunted by a mysterious curse, wary of outsiders. The party has to figure out what the curse is and how to stop it, while most of the community is being less than helpful. But perhaps the party is thereat the behest of a friend or relative of one of the party members. Reminds me of the Ghostlands storyline in OG World of Warcraft, as well.

 

[talien]

I love the essential elements of the Sleepy Hollow story: an isolated community, haunted by a mysterious curse, wary of outsiders. The party has to figure out what the curse is and how to stop it, while most of the community is being less than helpful. But perhaps the party is thereat the behest of a friend or relative of one of the party members. Reminds me of the Ghostlands storyline in OG World of Warcraft, as well.

Because it's been adapted to American culture, there's also the element that it may well be a prank -- or that (as other media has portrayed it) there's both a prank AND a real Headless Horseman, giving the party a red herring to deal with.

 

[Remathilis]

Because it's been adapted to American culture, there's also the element that it may well be a prank -- or that (as other media has portrayed it) there's both a prank AND a real Headless Horseman, giving the party a red herring to deal with.

I used a module that adapted the Irving story thusly: Brom and his gang of bravos pranked Ichabod, but he fell off his horse during the chase and died. In a panic, they staged it to look like the horseman got him (cut off his head and hid it) but that only caused Ichabod to rise up as the horseman for reals and hunt down the gang that killed him.