The gang have reached Fortree City, and Ash is determined to finally challenge the local Gym Leader. Heading straight for the Gym, Ash is disappointed to learn that Winona, the Gym Leader, is away for the day at Fortree's Feather Carnival, a celebration of Flying Pokemon (which is the type Winona specializes in). Proceeding to the main part of the city, the gang notice the inhabitants unique way of living in tree houses, and also find Winona giving kids rides on her giant Skarmory, and May decides she wants a go too. Meanwhile, Team Rocket encounter the Magikarp Salesman again, where he offers James a chance to buy a Chmiecho, a very unique Pokemon which has soothing tones. James, obviously having forgotten the million other times he's been swindled by this guy, happily accepts, until it turns out to be a Hoppip dressed as a Chimecho (surprise surprise!). However James anger quickly fades when he encounters a genuine Chimecho and makes it his own. With a new Pokemon in their squad, Team Rocket plan to use Chimecho's Heal Bell attack to capture Pikachu...
A young boy named Ash Ketchum embarks on a journey to become a "Pokemon Master" with his first Pokemon, Pikachu. Joining him on his travels are Brock, a girl-obsessed Rock Pokemon Trainer, and Misty, a tomboyish Water Pokemon Trainer who may have a crush on him. Ash and Co. end up traveling through various regions, including Kanto, the Orange Islands, and Johto, and then enter the Pokemon League competitions there.
Along the way, they run into many confrontations with Jessie, James, and Meowth, a trio of Pokemon thieves who are apart of an evil organization called "Team Rocket". But every time Team Rocket try to do their evil deeds, they fail thanks to Ash and his Pokemon.