The Headless Horseman of Sleepy Hollow

October, 1872.

Two people have already been found headless. Their names remain in the village records, but something more intimate has been taken from each of them. Five empty places remain in a supernatural ledger. Five nights remain before the last ride.

By day, your players follow contradictory records through Tarrytown, North Tarrytown, and the Hollow. They question a guarded heir, a private investigator, a chapel custodian, a printer, a livery keeper, and a physician. They compare names, seals, photographs, routes, wounds, and burial records while a community decides how much truth it can survive.

By night, the road belongs to the Horseman.

He never speaks, and that silence is part of the hunt. He communicates through distance, hoofbeats, stolen echoes, changes in the Head Ledger, and the terrible certainty that he has chosen where to ride next.

Every identity the investigators recover weakens him. Every life they protect changes the final reckoning. Every threshold crossed may turn a rescuer into the quarry.

The Headless Horseman of Sleepy Hollow is a compact American Gothic adventure for three to six characters beginning at 3rd, 4th, 5th, or 6th level. It is designed for five sessions of approximately three to four hours, with a four-session route for groups that need a tighter Halloween schedule.

This is not a strict retelling of Washington Irving’s story. It takes the dread, autumn atmosphere, uncertain folklore, and famous rider of Sleepy Hollow, then builds a new investigation around identity, historical concealment, pursuit, and the price of setting a record right.

AT A GLANCE

• 5e-compatible
• Levels 3–6
• 3–6 players
• Five sessions or a four-session route 
• Investigation by day
• Supernatural pursuit by night
• Visible Head Ledger pressure clock
• Adaptation guides with Expanded Digital and every physical tier
• Nothing essential behind a stretch goal

Inside the Book

Take a look inside The Headless Horseman of Sleepy Hollow.Below are spreads from the current color interior to show the illustrations, page layout, and reference tables. Final print appearance may vary.

Introduction: Enter Sleepy Hollow

Running the Hollow: A Guide for the GM

Seven Nights of Terror: Calendar and Act One

The Central Mystery: Who Is the Horseman Trying to Become?

The Horseman is not collecting trophies.

He is assembling a person.

When the adventure begins, a seven-entry Head Ledger has already marked two lives. Five entries remain unresolved. Each corresponds to something that was stolen, divided, misnamed, or deliberately omitted from the identity beneath the legend.
The investigators can see the Ledger changing. They know another ride is coming. What they do not know is why these particular people have been chosen, what the Horseman lost, or which version of the old story was designed to keep the truth buried.

The mystery moves through ordinary evidence and supernatural consequence at the same time. A translated letter may change the meaning of a route. A medical observation may contradict a cherished legend. A corrected name may make the Horseman visibly less complete. A protected witness may carry proof into the climax—or decide the investigators cannot be trusted with it.

No required truth depends on one class, spell, language, tool proficiency, or successful die roll. Failed checks cost time, trust, position, protection, or the quality of the proof. They do not quietly remove the only path forward.

The deeper question is not simply how to destroy a monster. It is what the living owe someone whose identity was erased, and how far that debt can be answered without offering another innocent life in payment.

The Head Ledger

The Head Ledger is an open table mechanic. Its seven places make the danger visible without giving away the solution.

When the investigators recover a stolen identity, the Ledger changes and the Horseman’s pursuit weakens in a way the table can feel. When they fail to protect a life or a record, the cost also becomes visible. Players do not have to guess whether their decisions matter.

The Ledger is both clue structure and pressure clock: a record of what has been lost, what may still be recovered, and how close the Horseman is to completing his purpose.
Inquiry by Day

Daylight belongs to records, relationships, and hard choices.

The party can compare archives, interview custodians, reconstruct routes, earn access, protect evidence, and decide who should hold the truth. Every essential conclusion has more than one source, and important information can move when an NPC is absent, hostile, or dead.

Useful abilities still matter. They save time, improve proof, reveal additional leverage, and help the party arrive at night with a stronger plan. They never become a hidden admission fee for the adventure.

Pursuit by Night

At sunset, investigation becomes movement under pressure.

Ten reusable road segments create lamplit corners, rail crossings, stone-wall lanes, harvest fields, orchards, cemetery gates, millraces, and fogbound bridge approaches. Each pursuit offers readable routes, people to protect, evidence to carry, and consequences that continue after initiative ends.

The party may intercept the Horseman, divert him, rescue someone in his path, preserve a record, or turn the hunt back toward its source. Fighting is possible, but victory is rarely measured by reducing one enemy to zero hit points.

A Covered-Bridge Climax Built Around Choice

The final confrontation at fictional Mercy Bell Bridge is an objective encounter. People, proof, custody, and the Horseman’s claim arrive together. The players can seize, carry, protect, reveal, negotiate, resist, or destroy—but the physical choices they make at the table determine what the ending becomes.

Five public outcome paths are supported:

Restitution: Restore an erased identity and dignity while accepting a real cost in the present.

Exposure: Bring present concealment into the open without assigning inherited guilt to the innocent.

Negotiation: Replace vengeance with a binding obligation to correct the record.

Resistance: Protect people, evidence, and truth while holding back the Horseman.

Suppression: End the immediate violence at the cost of leaving the underlying debt unsettled.

None is presented as a hidden correct answer. Each preserves something, burdens someone, or both.

The Characters you will meet

These people are not vending machines for clues. They make present choices, respond to how the party treats them, and bring different kinds of aid or resistance to the final night.

The Horseman. A literal, silent revenant with a legitimate grievance and a terrifying method. He is neither a misunderstood mascot nor an excuse for indiscriminate violence. His silence, route pressure, and incomplete identity make him more frightening than a speech ever could.

The Unexpected Heir. A woman who inherited property she never expected to own and an archive she never chose. She wants to survive, understand what now belongs to her, and build a future that is not dictated by a family record.

The Field Investigator. A disciplined private operative who hires the party as a specialist field team. She has no police powers. Her central choice is whether client confidentiality can coexist with public duty once the supernatural evidence becomes undeniable.

The Chapel Custodian. The keeper of fictional Mercy Chapel wants to protect the living and preserve the dignity of the dead. He must decide when caution stops being care and becomes another kind of silence.

The Printer and Translator. A professional whose knowledge of language, handwriting, and public records matters more than folklore. She insists on accuracy, consent, worker safety, and evidence that cannot be controlled by a single archive.

The Livery Keeper. A practical route specialist who understands horses, roads, seals, dates, and why a journey described on paper may not match the ground. He knows that a wrong turn in a record can survive for generations.

The Physician. A careful doctor and custodian of old examination notes. He wants to protect the living, preserve named remains, and distinguish observed injury from legend without turning the dead into spectacle.

Rich Locations to Explore

Tarrytown Station and Field Office. Steam, cinders, baggage, carriage schedules, and rail crossings place modern movement beside a legend that refuses to remain buried.

Main and Orchard Record Row. A walkable district of fictional printers, photographers, legal copyists, and translators. Ink, plates, notices, and contradictory records make it the human center of the investigation.

Mercy Chapel and Parsonage. A fictional mission serving mill, farm, and laboring households. Its ordinary rooms hold inherited records and present responsibilities—not occult clergy or automatic sanctuary.

The Hill Estate and Archive. Locked cabinets, survey plans, family seals, and a property transfer nobody expected. The estate offers access and protection, but it also shows how easily private custody can become public silence.

The Old Dutch Church, Churchyard, and Sleepy Hollow Cemetery District. Historically grounded, separately identified real institutions used for geography, atmosphere, and neutral record comparison.

North Tarrytown Surgery and Undertaking Rooms. A fictional physician’s rooms and undertaking yard where practical care, preservation of remains, and the difference between observation and legend matter.

The Pursuit Roads. Lamplit corners, rail crossings, stone walls, harvest fields, orchards, cemetery gates, millraces, and fogbound thresholds form a modular road network that can be rearranged for different routes and repeat play.

Mercy Bell Bridge. A fictional covered mill bridge over a tributary or millrace. It is the adventure’s stark Gothic stage, where the Horseman, the investigators, and the consequences of their choices finally meet.
 

Conversion Guides

The Expanded Digital package is planned to include:

• A screen-optimized adventure PDF.
• A print-resolution adventure PDF.
• The separate print-and-play packet.
• GM and player-safe map files.
• Head Ledger sheets, identity cards, route tracker, and GM reference sheets.
• Printer-friendly critical handouts.

The campaign runs from September 21 through October 9, 2026. Our target for base 5e digital access is October 16, 2026, after the campaign closes and only after the release gates pass. If manuscript, playtest, rights, accessibility, or PDF preflight work changes that target, I will tell backers promptly and explain the revised plan.

Physical books are planned as 6 x 9-inch print-on-demand editions with an estimated December 2026 reward window, subject to proof approval, funds settlement, shipping configuration, and printer schedules. Physical delivery before Halloween is not promised.

Physical rewards are currently configured for delivery within the United States. I will add another region only after its shipping, tax, replacement, and fulfillment costs are confirmed.

The base adventure is written for 5e-compatible play using SRD 5.1. Separate digital adaptation guides are included with Expanded Digital and every physical tier for:

• Daggerheart Compatible play.
• Pathfinder Second Edition.
• Tales of the Valiant RPG.
• Old-School Essentials.

The four guides are not add-ons and they are not stretch goals. Each will be delivered as a separate PDF after its system-specific rules, license, compatibility-language, and content review is complete. Only the compatibility marks and notices permitted by each publisher will be used.

Why Back Wyrd Sisters

Wyrd Sisters Publishing creates atmospheric 5e-compatible adventures rooted in Gothic literature, folklore, and difficult human choices. Previous releases include The Woman in White, Spring-Heeled Jack, Blood and Howl, The Bell of Ashen Hollow, and The Coffin Smugglers of Kingston Cove.

I use the same staged production process here: source review, manuscript gates, human playtesting, editorial approval, accessible handouts, PDF preflight, and physical proofing. The Headless Horseman of Sleepy Hollow will not be called complete until the required gates pass.

Reward Tiers

Core Digital — $5

The complete core 5e-compatible adventure PDF. This tier does not include the Expanded Digital table-support files, adaptation guides, or unlocked stretch content.

Expanded Digital — $15 (Early Bird $10)

The screen and print adventure PDFs; the separate print-and-play packet; GM and player Head Ledger sheets; seven identity cards; the seven-night route tracker; two-page GM reference; three core map sets in GM and player-safe forms; ten modular chase-road segments; printer-friendly critical handouts; all four adaptation guides; and every unlocked digital stretch goal.

Explorer Softcover — $35 (Early Bird $25)

A 6 x 9-inch softcover with a black-and-white interior, plus the complete Expanded Digital package.

Collector Hardcover — $45 (Early Bird $40)

A 6 x 9-inch hardcover with a black-and-white interior, plus the complete Expanded Digital package.

Full-Color Deluxe Hardcover — $85 (Early Bird $75)

A 6 x 9-inch hardcover with a full-color interior, plus the complete Expanded Digital package.

All physical tiers include Expanded Digital. Physical rewards are currently limited to United States delivery. Shipping is charged separately and displayed before a pledge is completed.

Optional Add-Ons
 

Backer Dedication — $5. Add one approved backer name or short dedication line to the book’s backer dedication page. Final character limit, content policy, and survey deadline will appear in the add-on description.

Digital Classics of Terror Collection — $125. Add the current Wyrd Sisters digital Classics of Terror library. The exact title and file manifest will be published with the add-on before launch.

Hardcover Classics of Terror Library — $300. Add the current Wyrd Sisters hardcover Classics of Terror library. The exact title, format, shipping, and fulfillment manifest will be published with the add-on before launch.

Stretch Goals

Our funding goal is $3,000. The campaign uses a focused three-goal ladder at $5,000, $7,000, and $9,000.

Nothing required to run The Headless Horseman of Sleepy Hollow is held behind a stretch goal. The full adventure, five remaining rides, Head Ledger system, maps, pursuit tools, and covered-bridge climax are part of the funded project. Every unlocked goal adds a new way to return to the Hollow.

Unlocked stretch content is delivered digitally to Expanded Digital and every physical tier. Stretch content follows its own production schedule and will not delay the base adventure.

$5,000 — Relics of the Unreconciled

Six minor relics tied to records, bells, roads, memory, black tack, and inherited obligation; complete 5e rules and provenance; six printable relic and evidence cards; and one optional side inquiry.
Target digital delivery: December 18, 2026.

$7,000 — The Roads Remember

Two optional route variants, five roadside hauntings, seven reusable pursuit complications, and drop-in GM scene cards with player-safe and GM route inserts. The ten planned base road segments remain in the core package.
Target digital delivery: January 15, 2027.

$9,000 — Voices from the Hollow

Six additional fictional residents with personal stakes, secrets, relationships, and consequences; six optional daylight inquiry scenes; portraits; and compact GM reference cards.
Target digital delivery: January 29, 2027.

Why This One

Sleepy Hollow remembers the Horseman. It has forgotten the person beneath the legend.

That is the part of the story I wanted to explore.

The Horseman here is literal, silent, and frightening. His grievance matters, but it does not excuse what he is doing to the living. The people in his path did not commit the original wrong. They do, however, have to decide what they will preserve, what they will reveal, and whether safety built on an erased identity can remain innocent once the truth is known.

I wanted an investigation where evidence matters because people matter. Where recovering a name can weaken a monster. Where protecting a witness can change the climax. Where a corrected record can be as powerful as a spell, and where every ending asks the players to live with what they chose.

The five-night structure gives the adventure urgency without asking the table to guess. The Ledger is visible. The next ride is coming. The roads are readable. The players can make plans, take risks, argue about custody, and feel the hunt change around them.

Then the road turns.

Bring a group that likes Gothic mysteries, difficult bargains, human consequences, autumn fog, and endings they will still be discussing after the last lantern goes out.

He is collecting heads to finish his own. Yours will do.

Laurie