As the name implies, the teachers and assorted staff of Ever After High.
- Voiced by: Jamieson Price.
One of The Brothers Grimm. The last word on anything that goes on in his school, Headmaster Grimm is hell-bent on tradition and rules. Woe to anyone who seeks to break them...
- Big Bad: For most the early webisodes, but especially in Thronecoming, where he decides to directly manipulate Raven into her destiny, until his HeelFace Turn.
- Control Freak: Headmaster Grimms defining characteristic is his obsession with rules, specifically his rules. He imposes that all students must follow their legacies, no questions asked, and spends most of the time telling everyone (that isn't of a higher status than he) what they cant do instead of what they're allowed to do, to the point where he acts more like a ruler or a general than a teacher.
- Dean Bitterman: Is he ever.
- Evil Counterpart: He is Apple's Well-Intentioned Extremist/Ambiguously Evil Counterpart, because of their similar opinions on the legacy system. While Apple believes it to be pretty much the world's proper order, Milton enforces it, and he's willing to use less than moral tactics to make sure it stays this way.
- Family Eye Resemblance: Has almost no resemblance to his brother Giles besides the same green eyes.
- Fat and Skinny: The Fat to Giles' Skinny, though he's more solidly built than fat. Played straight when they were boys.
- I Lied: Said oh so casually in Stark Raven Mad.
- Manipulative Bastard: In the Thromecoming special, Milton plans to convince Raven to sign the Storybook of Legends by showing her a fake vision of a Bad Future where she does not. Raven and Apple discover his ruse when he ends up Saying Too Much.
- My Greatest Failure: The Thronecoming special reveals that Milton talked Giles into going inside The Ogre's Cave when they were kids, despite their father's warnings. When they got scared, Milton ran and abandoned his brother. Though Giles wasn't hurt, the memory continues to haunt Milton and fuel his desire to keep Ever After on script.
- Orange/Blue Contrast: Wears cool blues and indigos in contrast to his brother.
- Real Men Wear Pink: As shown in "True Heart's Day" and "Spring Unsprung," the grumpy headmaster has a weakness for cutsie unicorn dolls.
- Well-Intentioned Extremist: It's implied he lied to Raven about breaking destiny to protect his students from an (as-yet unknown) evil.
- An excerpt from the second book reveals that Raven's actions may have begun to set her mother free, which is what he might have been trying to prevent.
- Voiced by: Cam Clarke.
Headmaster Grimm's brother and the former librarian. He was trapped in the Vault of Lost Tales underneath the school and cursed to speak only in riddle-ish by his brother.
- Batman Gambit: Orchestrates a rare benign one in Thronecoming. He tells the girls where to find the pages of the missing Storybook of Legends, when they were really gathering pieces of an incantation that breaks his babble curse.
- Early-Bird Cameo: He actually made his first appearance as a cameo in the "13 Wishes" special of sister series Monster High
- Eccentric Mentor: Of sort. Raven and Maddie look him for help and he really is eccentric.
- Family Eye Resemblance: See Headmaster Grimm's entry.
- Fat and Skinny: The Skinny to Milton's Fat.
- Forgiveness: In the Thronecoming special, he forgives his brother for locking him away in the Vault of Lost Tales.
- Hair of Gold, Heart of Gold: He had blond hair in his youth, and is the more friendly Grimm brother.
- Intergenerational Friendship: He's friends with Maddie and often have tea parties together.
- Mad Oracle: Knows as much about Ever After and the Storybook of Legends as Milton, but it's cursed to speak in nigh unintelligible riddles that make him sound "coo-roo-cuckoo".Maddie: Hey, Riddle-ish is not an exact language.
- In the Thronecoming special, the girls unwittingly break his curse.
- Magic Librarian: Though he has yet to show a genuine affinity for magic, he still was librarian of a boarding school for fairy tale characters.
- Orange/Blue Contrast: Wears warm reds, browns and orange in contrast to his brother.
- Adaptational Attractiveness: Downplayed. Most depictions of her is a very old ugly hag, here she is normal looking woman somewhere in her 50s.
- Adaptational Heroism: Well she's not the child eating hag of old, but she is still head counselor for evil students and engages in a few questionable actions.
- Crazy Cat Lady: Or at least an evil(ish) one.
- Moving Buildings: Her house can grow legs and run away.
- Reasonable Authority Figure: Quite unlike her boss, she's quite willing to hear out both sides and come to a diplomatic solution. In a website game storyline, she even helps guide Raven towards finding some banned books under Grimm's nose because Raven wants to be able to use magic for good without it backfiring.
A refugee from Wonderland, which has been sealed off ever since the Queen of Hearts went on a rampage. She replaced Apple's favourite teacher, Professor Gold, as the princess faculty adviser, and she refuses to say where Gold has gone...
Lead of his eponymous fairy tale. A magical man whose pipe attracts rats and children, now a Music Teacher. He has a daughter in school named Melody.
- Nice Guy: Very gentle and good-natured. In Melody's diary, she reveals that when her father's time came to relive his story, he spared the lives of the rats instead of drowning them, instead leading them out of the city.
- Reasonable Authority Figure: Seems to be this. For example, he accepts (and praises) Duchess' dance video in "Best Feather Forward" as her musical assignment.
- Enemy Mine: Royals and Rebels band together to foil Rumplestiltskin's attempts to flunk them—and do the extra credit.
- Greed: His main reason for being a Sadist Teacher.
- Sadist Teacher: See above description
- In his second appearance he'd given out an online test... and then crashed the entire Mirrornet so no one could take it, they'd fail, and get detention where again, they'd have to spin straw into gold for him.
Ever After High's Gym teacher. Appropriately, his first appearance has him supervising a running class.
- Irony: In the book A Semi-Charming Life the class she ends up teaching in Damsel-In-Distress which has such lessons as "Waiting" and "Screaming for Help". The irony comes from not only does Marian find the lessons hilariously ridiculous but because of her past with Robin Hood she is the furthest thing from a Damsel in Distress possible.
- The Mentor: In the book A Semi-Charming Life she takes Darling under her wing, and teaches the girl about being a true hero.