The episode starts with everyone building a stage in the Hundred-Acre Wood. Piglet asked what was going on and Pooh told him, "Don't worry, Piglet. You'll find out.". Later that day, everyone is in their seats andChristopher Robin appears and he introduces their play called "The Legend of Sheriff Piglet". As Roo opens the curtans, Owl and Gopher starts to sing their song about the hero of the play. In the next scene, we see Pooh, Piglet,Tigger, Rabbit, and Eeyore traveling through the hot desert on their wagon until they reached in the a town where the townfolks (who are Prairie Dogs) who are moving out of their city because of a gang of Horse Thieves. Piglet suggests that the town needs a sheriff and the town's sheriff gives Piglet his badge and promotes him to the job. Just then, the Horse Thieves arrive and their leader, Nasty Jack tells Pooh and his friends that since Sheriffs and Horse Thieves don't get along and plans to trounce Piglet. When Pooh suggests that Nasty Jack would be "Satified with a hug instead?", Nasty Jack just kicks their wagon and the heroes land in the Sheriff's office. Tigger then starts to tell them that they need to stand and fight against Nasty Jack, but Owl and Gopher interupt the conversation and tells them that they have no chance standing up against him. Rabbit starts to panic and ran out of the office and runs into Nasty Jack in a Tavern. He becomes a Bartender and serves the Horse Thieves Root Beers and Banana Splits with carrots on top (which disgusts Jack).
Pooh, Piglet, Tigger and Eeyore start to plan a rescue. Tigger starts to come in with a lasso tells Nasty Jack to drop Rabbit or he'll get roped. Pooh and Eeyore start to go in, but are put into barrels by the Horse Thieves. Tigger starts to do his lasso trick, but gets tangled up is used as a Yo Yo while Piglet and Pooh help Eeyore get out of his barrel. Nasty Jack starts to kidnap Piglet. Pooh and Eeyore come into the Tavern as "The Masked Bear and his Faithful Steed" and starts to battle with Jack with Ice Cream. As Pooh starts to ran out of his ammo, Nasty Jack accidently shoots the Piano and the Piano hits him and makes him land in the water tub outside the Tavern. As Pooh and Eeyore go into the sunset, Nasty Jack comes out of the Water and said, "I'm gonna have to do something about that Masked Bear". Later Pooh and his friends start to "Clean up this town" by sweeping the streets. Nasty Jack appears as a delivery person showing a Telegram for The Masked Bear. Pooh tells him that The Masked Bear isn't here, but he and the others would give him the message. Jack reads the message which only says "Help!", which frightens Piglet so much that he rushes to the Jailcell to hide.
While Rabbit and Tigger tried to get Piglet out of the Jailcell, Pooh and Eeyore starts to become The Masked Bear and his Faithful Steed again only to be captured by Nasty Jack. He gives a letter to Piglet and since Tigger and Rabbit can't read it, Christopher Robin appears and reads the letter saying that Piget must have a showdown at sunset and the Masked Bear and his Faithful Steed cannot help him for they are tied up and can't be freed. So for the sake of the Townspeople and with the encouragement of Rabbit and Tigger, Piglet decided to face Nasty Jack once and for all. As he stalls Jack so Pooh and Eeyore can come to the rescue, Owl and Gopher are in the mines singing a song to Pooh and Eeyore who are tied up in a mine wagon and Gopher lets go of the mine wagon and Pooh and Eeyore are rushed to the rescue, but as they got to Town, they missed Nasty Jack and they crashed into the Sheriff's Office. Piglet starts to tell Jack what important it is to be Sheriff of the town and as Jack was about to trounce him, the badge starts to fell out of Piglet. Jack starts to complain that he can't trounce Piglet anymore and wonders what is he supposed to do now. Piglet then tells Jack that he could be Sheriff now and that made Nasty Jack very happy. Later, Piglet was rewarded a metal by the Mayor. Pooh and Eeyore rode off into the sunset, and Owl and Gopher starts to end the story with a song about themselves, but the curtan closes on them and "The Legend of Sheriff Piglet" ends.