Winnie the Pooh's Spookable Fun is a Walt Disney video release containing five terror-themed episodes of The New Adventures of Winnie the Pooh, including "Things That Go Piglet in the Night", "The Monster Frankenpooh", "Rock-a-Bye Pooh Bear", "Pooh Moon", and "A Knight to Remember".

In a "Knight to Remember", during a rainy day in Christopher Robin’s attic, Pooh, Piglet, Tigger, Rabbit and Eeyore play a game of chess which ends up becoming a little too real. Next, in "Rock-a-Bye Pooh Bear", a stormy nightmare proves to be no picnic for Piglet. Now he's afraid to go to sleep and it's up to Pooh, Rabbit and Tigger to show their friend that dreary dreams do not come true.

During an ordinary day in Hundred Acre Wood, Winnie the Pooh sets out to find some honey. Misinterpreting a note from Christopher Robin, Owl convinces Pooh, Tigger, Rabbit, Piglet, Kanga, Roo, and Eeyore that their young friend has been captured by a creature named "Backson" and they set out to rescue him.

Pooh is so busy gathering up his friends' wish lists for Santa that he forgets to include his own. After retrieving the list and adding his own desires, he realizes he's late getting it where it needs to go. Off he goes to the North Pole on Christmas Eve, with pals Eeyore, Tigger, Piglet, Rabbit, and Christopher Robin missing him

It's Thanksgiving time in the Hundred Acre Wood and Winnie the Pooh and all his friends bring food for the big dinner. Piglet brings acorns, Pooh brings honey, Owl brings biscuits, Gopher brings lemonade, and Tigger brings ice cream. But then, Rabbit walks in and tells them their Thanksgiving dinner was unacceptable and informs them that a real Thanksgiving dinner includes turkey, cranberry sauce, and pumpkin pie, so Pooh and his friends set out to find those very items.

It's Christmastime in the Hundred Acre Wood and all of the gang is getting ready with presents and decorations. The gang makes a list of what they want for Christmas and send it to Santa Claus - except that Pooh forgot to ask for something. So he heads out to retrieve the letter and get it to Santa by Christmas...which happens to be tomorrow!

Winnie the Pooh and friends teach counting.

After Christopher Robin abandons them for college, Pooh and Piglet embark on a bloody rampage as they search for a new source of food.

Maddie is haunted by her past but when the mysterious Mike Donovan shows up, her life turns upside down and her inner demons take the physical form of a demonic bear.

On Halloween night, Pooh and the gang are ready for Halloween, but Piglet is too scared to join in.