Sleepy Hollow (TV Series)
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50 free Sleepy Hollow (TV Series) trivia questions with answers — trivia quiz, new questions added Oct 2026.
A soldier from the 1700s wakes up in the twenty-first century, and so does the headless rider he fought. That is the hook of Sleepy Hollow, the supernatural drama that turned Washington Irving's schoolmaster into a time-displaced hero and paired him with a modern police lieutenant, Abbie Mills. Over four seasons the pair fought demons, secret societies and a surprising number of famous names from early American history. This quiz covers the whole run: the pilot and its twists, the monsters of the week, the family secrets, the cast and guest stars, and how the series was made and where it was filmed. Questions on the later seasons, including the move to a new city and a new partner for Ichabod, are here too. It is written for fans who watched every week and for anyone planning a spooky trivia night. The opening questions are the gentlest, the later ones reward close viewers, and every answer comes with a short explanation.
30 of 50 questions with answers and explanations. Play the quiz
Q 01In Sleepy Hollow, Ichabod Crane is cut down on a battlefield before his enchanted sleep; which conflict was he fighting?
The American Revolution
The American Revolution is where Crane, a captain spying for George Washington, beheads the Horseman while taking a mortal wound himself. A spell then keeps him asleep for more than two centuries.
Q 02In Sleepy Hollow's pilot, the Headless Horseman is unmasked as which of the Four Horsemen of the Apocalypse?
Death
Death is the rider Crane beheaded in 1781, and he wants his skull back because it would let him summon the other three Horsemen. Crane and Abbie recover the head before he does.
Q 03In Sleepy Hollow's first-season finale, the sin eater Henry Parrish turns out to be which relative of Ichabod Crane?
His son
His son Jeremy spent two centuries trapped in a coffin and blames his parents for it. Once unmasked, Henry buries Ichabod alive in return.
Q 04Sleepy Hollow borrows Ichabod Crane's centuries-long sleep from which other Washington Irving story?
Rip Van Winkle
Rip Van Winkle dozes off in the Catskills after drinking with mysterious Dutchmen and wakes 20 years later. The series stretches that nap to more than two centuries.
Q 05Which English actor, later seen in HBO's Watchmen, plays the time-displaced soldier Ichabod Crane in Sleepy Hollow?
Tom Mison
Tom Mison trained at the Webber Douglas Academy, where a speech coach advised him to aim for period pieces. Sleepy Hollow then cast him as a man from 1781.
Q 06Ichabod Crane and Abbie Mills of Sleepy Hollow guest-starred in a 2015 Halloween crossover with which crime procedural?
Bones
Bones sent its sceptical scientist Temperance Brennan to examine a 200-year-old headless corpse beside the two Witnesses. The story finished on Sleepy Hollow, where she mistook Greek fire for napalm.
Q 07In Sleepy Hollow's third-season finale, Abbie Mills gives up her soul to power which mythical object?
Pandora's box
Pandora's box only works with the soul of a Witness inside, so Abbie steps forward and an ancient god is left mortal. Ichabod carries on without her for one final season.
Q 08In Sleepy Hollow's second season, a cursed coin is blamed for turning which general against George Washington?
Benedict Arnold
Benedict Arnold is the show's proof of what the coin does: it corrupts whoever holds it. Henry Parrish slips the same coin to Jenny Mills to set her against the new sheriff.
Q 09Timothy Busfield plays which Founding Father in Sleepy Hollow, a mentor Ichabod Crane found arrogant and eccentric?
Benjamin Franklin
Benjamin Franklin is delighted, when a time-travelling Abbie meets him, to hear how famous he still is. Crane only worked with him because George Washington ordered it.
Q 10Which Harold & Kumar star plays Andy Brooks, the Sleepy Hollow officer who dies in the pilot and returns undead?
John Cho
John Cho plays him as a remorseful walking corpse after Brooks has his neck broken in the first episode. Even dead, he keeps trying to protect Abbie Mills.
Q 11Which US network aired all four seasons of Sleepy Hollow, launching the drama on a Monday night in 2013?
Fox
Fox renewed the series only weeks after its premiere drew about 10 million viewers. By the fourth and final season the average had slipped to about 3 million.
Q 12Which actress, Rachel Robinson in the baseball film 42, plays police lieutenant Abbie Mills in Sleepy Hollow?
Nicole Beharie
Nicole Beharie trained at Juilliard after a childhood spent partly in Nigeria, Panama and the UK, where her father's Foreign Service work took the family. She left when Abbie died in season three.
Q 13In Sleepy Hollow's first season, where is Ichabod Crane's wife Katrina trapped, reaching him only in dreams?
Purgatory
Q 21In Sleepy Hollow's first season, a secret society of which soldiers steals a book that opens a doorway to Hell?
Hessians
Hessians aligned with the Horseman seize the Lesser Key of Solomon and start the ritual, but Abbie Mills throws the book into the pit and the doorway closes.
Q 22In Sleepy Hollow's first season, the Headless Horseman is lured into a magical cell built by which Founding Father?
Thomas Jefferson
Thomas Jefferson built the chamber, but it catches the Horseman only because the heroes bait it with his own skull, which nothing they tried could destroy.
Q 23Under interrogation in Sleepy Hollow, the Headless Horseman is revealed to be which former friend of Ichabod Crane?
Abraham Van Brunt
Purgatory holds Katrina because her own coven handed her over as punishment for saving Crane's life. To get her out, Abbie Mills has to agree to take her place.
Q 14At the start of Sleepy Hollow, Abbie Mills is about to leave town for training with which agency?
The FBI
The FBI course at Quantico was Abbie's way out of town until her mentor was killed and she stayed to fight the Horseman. She finally completes it between seasons two and three.
Q 15In Sleepy Hollow's early episodes, Abbie Mills's estranged sister Jenny is living in what kind of institution?
A psychiatric hospital
A psychiatric hospital took Jenny in because she insisted she had seen a demon in the woods, while Abbie, who saw it too, denied everything. Between stays, Jenny trained in combat abroad and hunted occult artifacts.
Q 16Before spying for George Washington, Sleepy Hollow's Ichabod Crane reached America serving which country's forces?
Britain
Britain brought Crane to America in its own ranks before he switched sides to spy for the Colonists. A British general once offered him passage home in return for the names of rebel spies.
Q 17In Sleepy Hollow, Ichabod Crane and Abbie Mills are the two Witnesses foretold in which New Testament book?
Revelation
Revelation casts the pair as its two Witnesses, and the show later adds that they must face seven Tribulations. Crane learns the first of them was the demon behind the Horseman.
Q 18Which actor, the voice of Mr. Krabs, plays Abbie Mills's mentor Sheriff August Corbin in Sleepy Hollow?
Clancy Brown
Clancy Brown plays a sheriff who is beheaded by the Horseman in the opening episode, yet keeps returning as a ghost to advise Abbie. His secret files on the town's mysteries become the heroes' archive.
Q 19Which original MADtv cast member and former 7 Up pitchman plays Captain Frank Irving in Sleepy Hollow?
Orlando Jones
Orlando Jones plays a sceptical police captain who cuts his finger and signs a lawyer's contract in blood, handing over his soul. The character departs after two seasons.
Q 20Which demon, named after an ancient god linked to child sacrifice, is Sleepy Hollow's main villain for two seasons?
Moloch
Moloch raised the Headless Horseman to start the Apocalypse, then died at the hands of his own protégé, who realised his master saw him as expendable. With him dead, that apocalypse cannot happen.
Abraham Van Brunt was engaged to Katrina until she broke it off for Crane, and he became the Horseman to take his revenge. He still believes he was meant to be the hero of the story.
Q 24In Sleepy Hollow's episode John Doe, a sick boy who speaks only Middle English comes from which early settlement?
Roanoke
Roanoke was not wiped out in this telling: the whole colony was carried into another dimension, sick but unable to die. Returning the boy to his village cures the illness on both sides.
Q 25In Sleepy Hollow's third episode, a Mohawk spirit is behind a string of suicides; what is its nursery-tale name?
The Sandman
The Sandman here is the spirit Ro'kenhronteys, and the only way to stop him is to enter his dream world. Crane and Abbie Mills survive by confronting and atoning for their own past guilt.
Q 26Which monster, stitched from the remains of fallen soldiers, does Ichabod Crane revive in Sleepy Hollow's second season?
The Kindred
The Kindred had been abandoned unfinished by its maker, who never found the means to give it life. Crane supplies the missing piece: the Headless Horseman's own severed head.
Q 27In Sleepy Hollow, which mythical monster guards the Sword of Methuselah, yet poses no danger to the Headless Horseman?
A gorgon
A gorgon has filled its lair with statues of earlier intruders, but the Horseman is immune to its curse. Crane and Abbie Mills trick him into killing it for them.
Q 28In Sleepy Hollow's second season, a demonic version of which storybook figure abducts ten-year-old Sarah Lancaster?
The Pied Piper
The Pied Piper is tied to the Lancasters by a family curse, and his bone flute puts Abbie Mills into a trance when Crane plays it. She later breaks the flute rather than hand it over.
Q 29In Sleepy Hollow's second season, Henry Parrish tries to awaken the town's witches using a copy of which American icon?
The Liberty Bell
The Liberty Bell copy needs more power than Henry has, so Katrina finishes the ritual for him. He is killed when Crane and Abbie Mills step in.
Q 30In Sleepy Hollow, Joe Corbin, whose father mentored Abbie Mills, is cursed to become which monster of legend?
A wendigo
A wendigo is what Henry Parrish's curse makes of Joe until a Native American artifact cures him. The beast returns in season three, and Jenny Mills is forced to shoot him.