Timmy gets a case of the Itchy Polka Dots on the day of the Flossmore Valley Fair. In order to take care of Timmy, it's up to Mr. Wisdom to read to Timmy a medieval story on how the Itchy Polka Dots got started. The story involves Squire Timmy going out on a dangerous and perilous journey to beyond the Not-So-Sure-Its-A-Forest to grab some polka berries from the Polka Berry Bush to make King Louie of Floss-a-Lot get cured from the Itchy Polka Dots. During his quest, Squire Timmy has an encounter with Merlys the Magician, Bubbles Hood, the Gingivitis Gang, and the Polka Berry Bush guardians the Cavity Goon and Miss Sweetie along the way. In the end, Brushbrush gets the Itchy Polka Dots.

The Cavity Goon and Miss Sweety plan to get rid of Brushbrush and Timmy by capturing Brushbrush as bait so that they can capture Timmy and hand him over to the Tooth Fairy.

Timmy dreams that he and Brushbrush are taken to a dream vacation to Molar Island. Timmy ends up helping the locals when the ancient crown of King Cuspid has been stolen by the Gingivitis Tribe and the island will sink if the ancient crown of King Cuspid is not returned to the hole it was placed over.

Timmy reads to his friends a western story, where Sheriff Timmy deals with outlaws Goony the Kid and Miss Sweetie when they come to Big Mouth Gulch.

Timmy and his friends go to the beach, but there is just one problem: Timmy cannot swim, and neither can Waxie! Timmy then imagines himself as a lifeguard where his friends are competing in a surfing competition against Goon Doggy.

The Adventures of Teddy Ruxpin is an American animated television series based on Teddy Ruxpin, an animatronic teddy bear created by Ken Forsse and distributed by toy manufacturer Worlds of Wonder. While some of the stories used in the TV series were adapted from the books, many were original and greatly expanded upon the world established there.

Pooh thinks that Christopher Robin has forgotten his lunch and he, Piglet, Rabbit, Tigger, Owl, and Eeyore hop on a school bus to give it to him at school. While on the school bus, they demonstrate and discuss the rules and safety of riding the bus.

Winnie the Pooh, Piglet, Tigger, Owl and the rest of the gang discuss all the dangers of strangers and how you should handle yourself should you ever come face to face with a stranger.