WARNING: Only spoilers from the current season (Season 3) are whited out.
The Founding Fathers, allies, and enemies from the past
- Badass in Charge: A high up leader of the colonists during the war.
- Badass Normal: A normal man tasked with leading Ichabod and other members of the American Revolutionary forces in a secret war against Moloch and his minions to prevent the Apocalypse, all in addition to the commanding US forces in the more conventional battles of the Revolution
- The Chessmaster: The writers took General Washington's Real Life skill at this trope and applied it towards making him the Badass Normal commander of a Revolutionary-era effort to fight off demons, the Four Horsemen of the Apocalypse and other supernatural threats in order to prevent the end of the world.
- Cincinnatus: President Washington's Real Life embodiment of this trope and admiration for the Trope Namer Cincinnatus served as a clue to solving a mystery in the penultimate episode of Season One.
- Cool Old Guy: Not only was he a brilliant leader, but Washington was smart enough to prepare to help Ichabod in his struggles in the present.
- Historical Badass Upgrade: General Washington accomplished many great things in Real Life; the show adds "battling the supernatural" to his already distinguished resume.
- Historical Domain Character: First president of the United States and what not.
- Posthumous Character: Washington is long dead by the time Ichabod awakens in the modern world, however his plans still help Ichabod in his fight against Molloch.
- Secret Keeper: In the penultimate episode of Season One, we learn that George Washington was aware that Ichabod was destined to become a Witness.
- Born in the Wrong Century: The same way as Crane, in episode 2x18 ("Tempus Fugit"). Truth in Television; for his time Franklin held very progressive views with regard to both women (possibly because he knew so many) and black people (from having his beliefs in white supremacy challenged in the 1760s to calling openly for the abolition of slavery in 1785). Which is no doubt why he greets Abbie more with delight than confusion. Well...partly why.
- Cool Old Guy: It's Benjamin Franklin, after all. He was a founding father of the United States and aided in a shadow war against a God of Evil.
- Dirty Old Man: Much like in reality, Franklin here is depicted as something of a flirt.
- Historical Domain Character: Benjamin Franklin was a real person, naturally.
- Historical In-Joke: The old "Tied a key to a kite in a storm" story? Actually happened. But he wasn't trying to prove where electricity came from. He was trying to destroy The Ghenna Key.
- Insufferable Genius: At least from Crane's experience as the man's student.
Grace (née Harris) Dixon was the head matron at Lachlan Fredericks' manor. Like Fredericks, Dixon was also aware of the supernatural evils outside of the manor. Revealed later to be Abbie's maternal ancestor. In the finale, Grace helps Abbie undo all that has happened after she is sent to the past by Katrina's spell.
- Almighty Janitor: Although she plays major roles in past(and future) events, she is introduced as a loyal housekeeper and midwife at Fredericks' manor. Season 2 reveals she had magical abilities that were as powerful as her warlock employer.
- Ancestral Weapon: Her journal has been passed down from generation to generation. It contains many spells and information compiled in preparation for future battles.
- Magical Guardian: To Jeremy Crane.
- No Good Deed Goes Unpunished: Helping give birth to and later raising Jeremy does not save her and her husband when his power manifests.
- Passing the Torch: In the Season 2 finale, before sending Abbie back to the present Grace directed Abbie to look at the blank pages of the journal and stressed the importance that Abbie continue to write in the journal as a part of her destiny.
- Reset Button: The spell she creates to reverse Katrina's Traveler's Spell is essentially this.
- Single Line of Descent: It was prophesied that a Biblical Witness would be born into her family. Since this is a rare female example where the surnames were changed by marriage, the name Grace was passed down to her descendants until Grace Abigail Mills was born.
- Spirit Advisor: To Abbie in 1x09, "Sanctuary". Her spirit helps Abbie uncover the maligned spirit haunting the mansion, and the birth that caused it.
A silversmith and revolutionary, who is also a demon hunter. He's a close friend of Betsy Ross and saves her niece from a mysterious illness.
- Demon Slaying: It's what he does when he's not doing dentistry or midnight rides.
- Depraved Dentist: In-Universe, Ichabod sees him as this and refuses to visit a dentist in the present due to his experiences under Revere's care.
- Gadgeteer Genius: He forged dentistry tools that can be assembled into a demon-killing gun, and created a metal container for an Artifact of Doom.
- Historical Domain Character: Revere is most prominently known for warning the Colonial militia of the approaching British forces before the battles of Lexington and Concord.
- Impossibly Cool Weapon: His dentist tools can be assembled into a gun to kill demons.
General William Howe
The Commander-In-Chief of the British forces in the American War of Independence, who dabbles in black magic, and considers Ichabod a personal enemy for defecting to the revolutionaries.
- Black Magic: He uses it to fight the revolutionaries, binding people to wraiths to root out spies, and raising draugar to capture New York.
- Better to Die than Be Killed: After being raised as a zombie, refuses to give Crane the "satisfaction" of killing him and steps into a rain of Greek Fire.
- Face Death with Dignity: He tries, but Ichabod waits a little too long, and Howe's troops rescue him.
- Get It Over With: Ichabod is send to kill him, but tries to persuade him to hand over the city instead, until Howe grows tired of his waffling and orders him to "do what you came to do."
- Historical Domain Character: William Howe was indeed Commander-In-Chief of the British forces in the Revolutionary War...
- Historical Villain Upgrade: ...one assumes he didn't raise undead armies and wraiths to fight the Continental Army, though.
- Large Ham: In his interactions with Ichabod, especially his final moments.Ichabod: I should have ended this long ago.Howe: I will not give you the satisfaction, turncoat! [steps into Greek fire, and disintegrates, screaming]
- Revenant Zombie: He gets resurrected by Pandora and has only one goal: killing Crane.
- Worthy Opponent: Ichabod used to greatly admire him before the war, and thus views him as this. Abbie points out that he must have changed since then, given that he resorted to black magic.
Sleepy Hollow Police Department
Det. Luke Morales
Abbie's co-worker and ex-boyfriend.
- Cassandra Truth: Tries to convince his colleagues that there is more going on within the precinct and that Captain Irving is hiding the truth behind the cases they're covering. By the time he learns the truth, he's too traumatized to act.
- Chuck Cunningham Syndrome: He hasn't been seen at all in Season 2.
- Cowboy Cop: Former military veteran, has Jerk with a Heart of Gold tendencies, and repeatedly goes against Captain Irving's orders to stop investigating Ichabod.
- Demonic Possession: Possessed by Ancitif in Season 1.
- Heroic Safe Mode: Does his best to keep his head down and do his job after his run-in with Brooks.
- Inspector Javert: Starts nosing around trying to figure out Ichabod's background.
- Sanity Slippage: He's badly shaken after his confrontation with Brooks and he's beginning to question what happened.
- Those Two Guys: Often seen with his partner, Devon.
- Tragic Bromance: Ancitif kills Devon while in Luke's body.
- What Happened to the Mouse?: He was last seen unconscious on the floor after Ancitif successfully possessed Macey, was not seen or mentioned again in later episodes.
- Working with the Ex: Abbie is his ex-girlfriend.
Andrew 'Andy' Brooks
Abbie's co-worker and friend. He was revealed to be affiliated with the coven that resurrected the Horseman and, despite having his neck broken in the pilot for his failure, has since returned as an undead being to aid other spirits in their efforts to be reborn.
- Agent Scully: Except not really, since he works for a demon after all.
- Apologetic Attacker: He's rather reluctant in following the Moloch's orders; so far, he's apologized in one way or another to all his victims.
- Back from the Dead: Moloch revives him presumably out of pragmatism.
- Body Horror: Moloch resurrects Brooks in "Blood Moon." Problem is, he doesn't restore his completely snapped neck until after he's been resurrected. And since he's still basically just a walking corpse, he continues grossing grossly in the gross. In "The Indispensable Man," he is transformed into a more distorted form of himself with an "egg"-like head.
- Came Back Wrong: Brooks is left considerably less than human after being resurrected by Moloch.
- Deadpan Snarker: "No, really. I don't need any help as long as you're comfortable." Said to a 200-year-old homicidal witch.
- Eerie Pale-Skinned Brunette: Notably when revived as a zombie.
- Fair Cop: At least before being resurrected the second time.
- First-Episode Spoiler: After the small twist in the first episode that he's working for a demon, he's seen frequently in other episodes.
- HeelFace Revolving Door: He is simultaneously forced to work for Moloch and wanting to help Abbie. This results in him alternating unpredictably between being helpful and being a minor antagonist
- The Mole: For Moloch, but he's revealed in the first episode and from there on is a more traditional henchman.
- Mouth of Sauron: Brooks acts as a medium for the Horseman to speak through.
- Noble Demon: Possibly. Doesn't seem to enjoy his job as a demon gofer and seems to genuinely want to help Abbie.
- Our Zombies Are Different: After being killed, Moloch resurrects him to do his bidding.
- The Renfield: Essentially plays this role to the Big Bad in a non-vampire example.
- Villainous Crush: He has an unrequited romantic interest in Abbie.
- Villainous Rescue: Stops the Horseman from killing Ichabod in "Necromancer."
- You Have Failed Me: Moloch kills him after he's arrested.
Sheriff August Corbin
Abbie's mentor and father figure, who was decapitated by the Horseman of Death during the Horseman's return. Corbin was aware of the secrets of Sleepy Hollow and collected extensive records.
- Agent Mulder: That said, he stockpiles data and as much proof as he can find.
- The Chessmaster: While he was the mentor to Abbie, he was secretly also the mentor to her sister Jenny, orchestrating things so that they'd eventually have to work together and begin to mend the rift in their relationship.
- A Father to His Men: Abbie looked up to him as a father figure.
- Mentor Occupational Hazard: Is killed by the headless horseman, leaving Abbie to develop alone.
- Off with His Head!: Corbin is the first victim of the Horseman within the chronology of the series.
- Our Ghosts Are Different: He appears as a ghost to Abbie—and only Abbie, so far.
- Parental Substitute: To Abbie and Jenny. After their encounter with Moloch, Corbin was always looking out for them in some way.Abbie: I got more fathering in five minutes than I did my whole life.
- Posthumous Character: It's only after he dies that he becomes important.
- Spirit Advisor: He briefly appeared as this to Abbie.
Sheriff Leena Reyes
- Hero Antagonist: She might be a thorn in the heroes' side and causes lots of problems, but everything Reyes does makes sense from her standpoint. She has no idea about Sleepy Hollow's true nature and does the best she can with the knowledge she has.
- Iron Lady: As a Sheriff, she's tough and doesn't suffer fools gladly.
- Reasonable Authority Figure: Reyes is an antagonist, but she's actually very reasonable. She treats Abbie well, even apologizing to her in private for the use of the word 'sanity' which she thought might have been seen as insensitive. Reyes also treats Frank Irving very kindly despite him being (to her knowledge) a murderer; she shows him sympathy and wants him to get the best psychiatric treatment.
Det. Devon Jones
Luke Morale's partner on the force who dreams of moving up to the NYPD detective force. While he shares Luke's doubts of everything going on, he doesn't want to land on the new police chief's bad side.
- By-the-Book Cop: Is more than happy to follow orders, no matter how questionable they seem.
- Fair Cop: Sleepy Hollow PD has no shortage of these.
- Forgotten Fallen Friend: He has been only indirectly mentioned in season 2 as Irving was arrested for his and Father Boland's murder.
- Friendly Target: Killed by a possessed Luke Morales in 1x08.
- Nobody Calls Me "Chicken"!: How Anticif-as-Luke tricked Devon into removing the barrier preventing demons from entering the safe house.
- Not Now, Kiddo: Played with. Even though he believes what Luke is telling him, Devon still tries to get Luke to focus on their future promotions within the force instead of digging around for dirt on Ichabod Crane.
- Those Two Guys: Often seen talking to Luke.
The daughter of Cynthia and Frank Irving. She is in a wheelchair after being hit by a car. Her parents are divorced and she lives with her mother.
- Affectionate Nickname: Irving often calls her "little bean."
- Black and Nerdy: Macey gets top grades and is hoping to join an AP science class.
- Bratty Teenage Daughter: Downplayed. She's snarky when confronting Jenny, whom she thinks is her dad's new girlfriend, and she has some issues with Irving, but other than that, she's still a sweet girl who's usually easy to get along with.
- Daddy's Girl: While she has her issues with Irving, she's quite close with him.
- Demonic Possession: She gets possessed in "Vessel" when Irving fails to deliver Washington's Bible to Ancitif. Thankfully, Ichabod and the Mills sisters stop Ancitif in time.
- Disabled Snarker/Little Miss Snarker: To an extent. She's certainly not afraid to speak her mind.
- Nice Hat: She's seen wearing one in each appearance.
- Plucky Girl: She's very upbeat and is quick to tell Irving that she's going to come out strong."I mean, no matter how scary this gets, I'm not gonna let this thing beat me, right? I'm gonna keep fighting."
- Quirky Curls: Her standard hairstyle.
- Amicable Exes: While she does take issue with Irving keeping things from her, they get along for the sake of their daughter.
- Aloof Dark-Haired Girl: She has a very stoic demeanor.
- Hello, Attorney!: Both an attorney and a hot mom.
- Locked Out of the Loop: At least until "Vessel" after she sees Macey's possession first hand.
Nicholas "Nick" Hawley
An artifact hunter who finds himself thrust into the supernatural war in Sleepy Hollow.
- Arbitrary Scepticism: He's perfectly happy with using sanctified stained glass to contain the betrayal-inducing power of a Tyrian shekel, but dismisses the idea of the Pied Piper being a supernatural menace until he fights it himself.Hawley: It was my first real, live monster.Abbie: You deal in supernatural armaments, Hawley.Hawley: Do people who sell Christmas trees all believe in Santa Claus?
- Badass Beard: A blond one, similar to Ichabod's own.
- Crazy-Prepared: Due to his business, when it comes to facing the supernatural 9/10 he'll have something that can help.
- Deadpan Snarker: It's part of his Lovable Rogue ensemble.
- Foil: To Ichabod, to the point where even there hair colour is an inversion.
- Friends with Benefits: With Jenny, at one point.
- Genre Savvy: One of his first responses to finding out the supernatural is real and the apocalypse is occurring is to start researching and arming, so he's prepared if he comes to meet it.
- Jerk with a Heart of Gold: He's a greedy, selfish ass who only cares about his next payday. But he does have a knack for helping save people from supernatural objects and creatures.
- Lovable Rogue: Is dismissed by Ichabod as nothing more than a Privateer, interested only in money. However Nick's charismatic, and has a strong sense of honour. Likewise he will put saving people above his pay, he just prefers to secure both.
- Not in This for Your Revolution: He's not worried about the End of Days. He's hunting valuable artifacts.
- Revolvers Are Just Better: His weapon of choice is a revolver, which following discovering the supernatural he fills with rare consecrated bullets so that its especially effective against the supernatural.
- One Head Taller: Mirroring Crane and Abbie, Hawley is over half a foot taller than Jenny.
- Only in It for the Money: A fact he makes abundantly clear to Abbie and Crane. Begins to soften up as the series goes on, but still never looses sight of his pay day.
- Put on a Bus: In "Kali Yuga" he leaves Sleepy Hollow to track down his demonic godmother Carmilla Pines.
- Screw This, I'm Outta Here!: After his encounter with the Pied Piper, he washes his hands of Abbie, Crane and their fight against demons and monsters. However, he promptly returns in the next episode and admits he just panicked as it was his first true encounter with the supernatural.
- Skeptic No Longer: Following his encounter with the Pied Piper, he's a believer.
- Born in the Wrong Century: Participates in colonial war reenactments as a hobby, is able to sew clothes and deliver food made in a method Ichabod is familiar with. She and Ichabod bond over the Ye Goode Olde Days and her reenactor group.Caroline: We can't have you showing up to the Battle of Saratoga with a button missing, can we?
- Chekhov's Hobby: Knowing how to weave fabric and sew 18th century fashions later proves to be a solution to Ichabod's Limited Wardrobe problem.
- Due to the Dead: Abbie and Ichabod help arrange a memorial service for her.
- Didn't See That Coming: Decided it was safe to seduce Ichabod because she was under the impression he was a Confirmed Bachelor.Caroline: You live alone. You never talk about her. There's no photos of her around. I assumed you were single or... separated or... a widower.
- Fake Brit: In-universe she speaks with a British accent during reenactments.
- Friendly Target: The Weeping Lady took issue with any woman that Ichabod cared about.
- I Dont Wantto Ruin Our Friendship: When Ichabod visited to make things right after hurting Caroline's feelings.Ichabod: It was a misunderstanding, one that I pray that we can put behind us. Truth be told, I have precious few friends in Sleepy Hollow. And none that share my fervor for the colonial way of life.Caroline: Of course we can still be friends, Ichabod.
- Interrupted Declaration of Love: By Ichabod himself.Ichabod: Miss Caroline...words cannot express how flattered I am.Caroline: Then don't use words-Ichabod: I'm a married man!
- Mistaken Identity: When Ichabod meets Caroline, he thinks she is Katrina at first due to her red hair and 18th century dress. After following her to a war camp, he tries to make sense of where he traveled back in time, she breaks character out of confusion.
- Nerds Are Sexy: Develops a crush on Ichabod because she admires his fierce dedication to colonial life.
- Not What It Looks Like: Said word for word by Caroline after Abbie walks in on her Interrupted Declaration of Love, to which Ichabod has to quickly explain that She Is Not My Wife.
- Only One Name: Her last name is never mentioned.
- Stuffed into the Fridge: Her close friendship with Ichabod is the sole reason she is targeted by The Weeping Lady.
- Tragic Keepsake: Along with the clothes and items Caroline made for Ichabod, he also keeps the 'I Love Founding Fathers' mug Caroline was holding on the night she died.
- Walking Spoiler: Her role in season two is this.
- Your Favorite: Tries this in hopes Ichabod will realize she has feelings for him. Those gifts are later turned into Tragic Keepsakes.Caroline: I made you some new shirts, breeches and hose all cut from cloth woven on a Hartford-Saxony loom. I also brought you butter I churned last night, some loganberry preserves, and... -holds up handmade pillow embroidered with Ichabod's initials-Ichabod: Miss Caroline, your generosity knows no bounds.
A member of the Historic Society in Sleepy Hollow, who meets Ichabod while he is trying to save the archives from impending demolition.
- Brainy Brunette: She's a well-versed history enthusiast, who delights in trading quotes and facts with Ichabod.
- Nerds Are Sexy: She develops an interest in Ichabod after he takes his leave of her with a perfect gentlemanly bow.
- Suspiciously Similar Substitute: She shares her sunny personality and her enthusiasm for both history and Ichabod with Caroline.
A relic hunter and old acquaintance of Jenny's, who is after the Shard of Anubis, an artifact that is in her possession.
- Affably Evil: Is happy to resort to kidnapping and theft in his hunt for relics, but he's still pretty friendly, reasonable, charming and witty while doing so.
- Deadpan Snarker: Makes quite a bit of fun of both Jenny and Joe in their interactions, even after they find him in a very compromising position.
- Handicapped Badass: For a guy with a limp, he can still go toe to toe with Jenny in a fight.
- Honeytrap: He walks straight into Sophia's, and ends up handcuffed in the shower, while she tricks Jenny and Joe, and escapes with the above-mentioned artifact.
- Hostage for MacGuffin: He kidnaps Joe to force Jenny into handing over the Shard of Anubis. She does, but he doesn't keep it for long.