Original airdate (Twitch): October 23, 2021
The stranger is a were-raven member of the strange, unknown organization that has been using ravens to keep track of the current events in Barovia. He requests that the party deal with the Pumpkin King for him, and then meet him at the Blue Water Inn in Vallaki to the north. Heading to Pumpkin King Jack's ghostly town posthaste, Brand instantly hits it off with him, and they learn the reason for Jack's "antagonism" towards the were-raven: a simple misunderstanding. When the party asks about other large birds in the area, namely if Jack had seen Sumer, he reveals that their old Kenku ally is not the only supposedly dead figure from the past that's still walking around. Noticing how stressed the party is over current events, Jack lightens the mood by creating a carnival; while some benefit, others suffer, and nobody knows what Jack has in store for the main event.
- Back from the Dead: When the party asks Jack why Sumer came near his territory, Jack drops a Wham Line as he casually notes that Sumer was probably just tracking Zaro von Strahdovich, AKA the Necromancer that killed Calamity and the remaining party had slain in the first season finale.
- Call-Back: One of the attractions at the Carnival is labeled "Face Your Fears", but it's closed down for repairs after what happened a week ago.
- Crossover Punchline: Like the pervious year, everything related to Mad Jack is a reference to a wrestling EFederation that Bosco runs part of. This includes every character in the carnival, who are wrestlers in that EFed.
- Feathered Fiend: One of the attractions is a duck pond where you can bob for potions. Grymharl tries it, but the ducks turn out to have monstrous teeth, and all she can get after numerous attempts and bite wounds is a regular Health Potion.
- Improbable Aiming Skills: Raykhul manages to win a game of "sportsball" (basketball) against one of the carnival employees with a few trick shots, including one where he throws two balls at once and they both score. Later, Kapnos manages to hit the target of a dunk tank and drench Mad Jack on his first attempt.
- Morphic Resonance: All of the "employees" at Mad Jack's Carnival either have the Pumpkin King's orange skin and glowing eyes, or the Night Reaper's red eyes and deep voice, regardless of the species they appear as.
- Serious Business: The last attraction before the Big Top at the end of the carnival path is a game of musical chairs, which the party gets incredibly competitive over, with Grymharl shoving people out of the way and Raykhul moving a chair with his tail just as one of his friends is about to sit on it.
- Shipper on Deck: When Grymharl asks the "Meme Machine" for a fortune, she doesn't want one for herself, and would rather know if her boss (the Werewolf Alpha) will find love with Sophia.
- Shout-Out: When the party reaches the "Meme Machine", a fortune telling robot, three party members decide to use it, and the fortunes they get are song lyrics from wrestling entrance themes.
- Stating the Simple Solution: Jack had observed a large raven prowling his territory in bird form, and failed to communicate with him in any of the avian languages he knows, including hawk and eagle. The party then informs him that it was a were-raven, and ask if he'd ever just tried speaking Common; he's embarrassed at never considering it earlier.
- What You Are in the Dark: One of the attractions at Jack's carnival is "Inquisition Interrogation", which Wihakayda enters. The being inside accuses her of being a monster in disguise, and offers her a fresh corpse to sate the hunger in her that's been growing since she last fed a week ago. Despite none of the other party members being present, Wihakayda refuses to devour someone innocent, and chooses to make a small grave and leave instead of sating her hunger.
