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MeiAn amnesiac Winged Humanoid with magical powers, Mei came to Questport to search for information related to her Mysterious Past and strange dreams. Instead, she was caught up in the chaos of the Master of Darkness's reappearance and became part of the Fellowship.
- Action Girl: Takes on the Prince of Shadows and Illusions, and holds her own.
- Amnesiac Hero: She can't remember anything before three years prior to the start of the first quest.
- Blow You Away: She's a wind mage.
- Dreaming of Times Gone By: She has dreams about the death of her family and the imprisonment of The Prince of Shadows and llusions, among others.
Gawain of the Oaktree ClanAn elven ranger who was abandoned by his parents at a young age. He was raised by a human blacksmith; after a plague wiped out the village where he lived, he journeyed to Questport to become an adventurer.
- Put on a Bus: He's inexplicably absent from Year Four.
Shadowa MoonA vampire, and Dracula's niece. After the Master of Darkness destroyed her home, she fled to Questport and eventually became a member of the Fellowship.
- Dark Is Not Evil: Skilled at dark magic.
AtoAn elven assassin who became a member of the Fellowship after being trapped in Questport during the Master of Darkness's attack. Known for smuggling knives into the Questport Temple and always wearing a mask.
- Demonic Possession: A voluntary (though very reluctant) example.
- Grand Theft Me: Is possessed by a demon during Year Four.
- Parental Abandonment: He's an orphan, and it's never made clear what happened to his parents.
EmmyA fairy who came to Questport to earn money for her family after a terrible storm destroyed their home. Instead, she found herself caught up in adventures as a member of the Fellowship.
ScorpioOnce a human entrepreneur, Scorpio was transformed into a dragon by an evil wizard. Even after obtaining the crystals that would allow him to change back, he chose to stay in his scaly form and became part of the Fellowship.
- Breath Weapon: He can breathe fire and spit poison.
- Transformation Trinket: Four blue crystals.
- Voluntary Shape Shifting: Now that he has recovered his crystals.
SpiroA demon transformer who was employed by the Lord of Angels and Demons but was banished from his homeland after showing mercy to a helpless Demon Bunny. Now a member of the Fellowship.
- Heel–Face Turn: After being banished from Hybris.
TulipA pixie who came to Questport just for the fun of it. Despite her small size, she's as brave as any of the other heroes in the Fellowship.
The Lord of the Supreme Council (Sabriel DuLac)Sabriel DuLac rules the village of Questport as the ruler of the Supreme Council. Under her rule, Questport is experiencing a renaissance of sorts, despite the rash of villains bent on taking over the world. Perhaps her most important decision as the Lord of the Supreme Council was to welcome the eight strangers who wandered into the Questport Temple one morning and suggest that they undertake a dangerous quest...
- Aloof Big Sister
- Badass Normal: Unlike the vast majority of Questport characters, she shows no sign of being able to use magic.
- Complaining About Rescues They Don't Like / Unwanted Rescue: She had everything completely under control.
- A Day in the Limelight: The main narrator in Year Five.
- Distressed Damsel: After being captured by the Queen of Rogues and Robbers in the second year.
- The Glorious War of Sisterly Rivalry: With her irresponsible younger sibling, Lirael (better known as the Queen of Rogues and Robbers).
- Shout-Out: Her first name, Sabriel.
- Silk Hiding Steel: Occasionally, although she's usual an Iron Lady.
The Head ScholarThe youngest member of the Questport Supreme Council, charged with recording the exploits of the Fellowship in the Questport Chronicles.
The Lord of Angels and DemonsThe sophisticated, manipulative, and annoying ruler of Hybris. The Lord of Angels and Demons is a frequent foe and sometimes ally of the Fellowship, and will stop at nothing to achieve his goals.
- Butt Monkey: He seems to be becoming this as the quests continue.
- The Casanova: Subverted. He seems to be genuinely in love with everyone that he falls for.
- A Day in the Limelight: One of the protagonists of Year Five.
- Embarrassing First Name: Word of God says that his real name is Ack.
- Evil Gloating: Doesn't hesitate to indulge in this.
- Friendly Enemy: To the Fellowship.
- Griping About Gremlins: He employs gremlins as servants and spies.
- Heel–Face Revolving Door: Switches sides too many times to count.
- Lady Killer In Love: With the Queen of Rogues and Robbers.
- Manipulative Bastard: He's perfectly fine with using the Fellowship to suit his own ends.
- Nice Job Breaking It, Hero: Nice job releasing the Prince of Shadows and Illusions.
- Our Angels Are Different / Our Demons Are Different: He's a demon transformer.
- Psycho Ex-Boyfriend: Erases the Secret Keeper's memory after she dumps him.
- Running Gag: Every time he escapes from prison, he's missing another article of clothing.
- Serial Romeo: Falls head-over-heels in love with the Secret Keeper, the Sphinx, and the Queen of Rogues and Robbers.
The Queen of Rogues and Robbers (Lirael DuLac)Introduced in the second year, the Queen of Rogues and Robbers has since become a recurring annoyance, along with her partner in crime, the Lord of Angels and Demons.
- A Day in the Limelight: One of the protagonists of Year Five.
- The Glorious War of Sisterly Rivalry: Deeply resents being compared to her older sister.
- God Save Us from the Queen!: Although it's unclear whether she actually rules a kingdom.
- Jerk with a Heart of Gold: Despite her villainy, she has helped out the Fellowship at times, and even returned Emmy's spells after stealing them.
- Obfuscating Stupidity: More like Obfuscating Vanity.
Jaheira and AcreA pair of druids who first appear in Year Two. In addition to providing the Fellowship with plenty of Healing Potions, they also transform the Yostwell's Light into the Tree of Light.
The Master of DarknessAn evil sorcerer who conquered the world a thousand years ago. He was defeated by the original Fellowship and thought to be banished forever, but returned to menace the world yet again.
- Dark World: Most of the world becomes this after he takes over.
- Never Found the Body: After his first defeat.
- Offstage Villainy: Doesn't show up until the very end of the year.
The Prince of Shadows and IllusionsAn ancient, evil being that was defeated by the Yostwell millennia ago and trapped in a mirror. After the Lord of Angels and Demons reversed the spell by mistake, it escaped and vowed revenge against the whole world.
- Offstage Villainy: Similar to the Master of Darkness, he does not appear until the very end of the quest.
The MageA mysterious magician whom the Fellowship encounters on their third quest. Despite his unimposing appearance (at least compared to the previous two Big Bads), he is responsible for the single most heinous act in the entire saga: the destruction of Questport.
- Addictive Magic: He depends on the essence of Aether to recover from the effects of using Gaudior's Horn. This doesn't end well.
- Hoist by His Own Petard: Dissolves into Aether after overusing the essence of Aether for his spells.
- Light 'em Up: Specializes in light magic, leading to...
- No Name Given: Neither the Fellowship nor the audience ever learns his real identity.
The Dark Swine (Rodrigo Noire)A demon summoned from the netherworld by the Fellowship. Constrained within the body of one of the heroes (Ato), it is forced to lead them into the netherworld to recover the soul of the Lost Lady.
- Eldritch Abomination: Possibly. The demons of the netherworld are said to be far older and more powerful than most spirits.
- Exact Words: It swore to take the Fellowship safely to the Lost Lady. It didn't say that it would help them leave the netherworld.
- Names to Run Away from Really Fast: Continuing a trend among the Chronicles' villains.
- Our Demons Are Different: Most of the demons in Questport are demon transformers; the Dark Swine, however, shows no sign of transformation.
- Roaring Rampage of Revenge: It is not happy about being imprisoned in a corporeal body, and takes its anger out on the Questport inhabitants.
Dwayne of the Oaktree ClanAn elf with daddy issues, who becomes the Master of Darkness's top lieutenant in an Alternate Universe where the Fellowship was never formed.
- The Reveal: Gawain is his father.