In Boo For You! Halloween, Captain Jake befriends a baby Halloweasel that follows him around while looking for pumpkins. But when Night Ninja and his Ninjalinos plan to steal all the candy from the festival, the PJ Masks, along with their new helper, must stop them before the festival is ruined!
The episode begins at the Pumpkin Patch where Captain Jake and his crew, along with Kwazii and Sofia, are picking pumpkins for the Boo For You! Halloween festival. Just then, Captain Jake was about to pick another pumpkin when a baby Halloweasel hops onto it as Captain Jake asks it to get off. But the baby Halloweasel refuses and rolls away with it, then Captain Jake chased it.
Suddenly, the Halloweasel trips on a small rock and tumbles off the pumpkin. Captain Jake catches the Halloweasel just in time before it hit the ground. After saving it, the Halloweasel rubbed his cheek against Captain Jake's face to thank him when Kwazii, Sofia, Izzy, Cubby, and Skully ran over to see what was going on. Sofia immediately saw the Halloweasel in her friend's arm and noticed how cute he was as she takes out her camera and takes a picture of it. Captain Jake then names the Halloweasel Tumbles because he tumbled from the pumpkin just after putting Tumbles back on his pumpkin and waving goodbye to him before going on the truck of pumpkins with his friends. But little did he and his friends know that Tumbles have hopped into the truck and rode along with the other picked pumpkins in the back while he settles in.
Later, at the town plaza, Captain Jake and the others were bringing the pumpkins out of the truck. But just when Captain Jake was about to take another pumpkin out of the truck, Tumbles pops out of nowhere and hops onto the pumpkin, startling Captain Jake! Laughing, he takes Tumbles out of the truck and holds him up, asking him how he got in until Captain Jake realizes that he must have hitched a ride on when he and the others weren't looking. Kwazii suggests that they should take Tumbles back to the pumpkin patch, but Captain Jake decides that Tumbles should stay with him and enjoy the festival until it's time to take him home as he picks him up and puts him on top of his captain hat. Kwazii agrees, even though he was a little unsure.
When the festival began, Captain Jake (in his Peter Pan costume) and his friends (also in their Halloween costumes), including Tumbles (who is now dressed as a pirate), we're having a great time playing games like bobbing for apples (both Pearl and Tumbles bobbed for the most and won some prizes), pin the tail on the black cat, whack-a-zombie, and ghost shooting. Captain Jake even won a pumpkin pendant for Tumbles after winning the game. Just then, Mayor Mickey calls to everyone so he can announce the winner of this year's Boo For You! Halloween Candy Basket Marathon as Minnie holds out a plastic pumpkin-shaped Halloween basket filled with raffle tickets inside and Mickey puts his hand inside to pull out a ticket that had Captain Jake's name written on it. Which means... Captain Jake is the winner! While Tumbles was jumping up on his head with excitement, Captain Jake walked up onto the stage to claim his prize.
But as Goofy unveiled the prize filled with candy and treats, it was gone! While everyone was groaning miserably, Connor, Amaya, Greg, and Captain Jake (with Tumbles wrapped around his neck) huddle together to talk secretly. Amaya thinks that maybe a nighttime villain must have stolen the big bucket of Halloween treats, so the four kids hold out their fists to form a pact and run over to Kwazii to ask him to bring their pajamas with his appearing magic.
So with a flick of his paw, Kwazii makes the four pairs of pajamas appear in his arm and gives each pair to his friends. But they didn't notice that Tumbles snuck into Captain Jake's goldfish pajamas as they transformed and went to HQ.