Ash and friends climb the steps to the Fortree City Gym—only to find out that the Gym Leader is busy in town with the Feather Carnival. Ash quickly heads to the carnival, where Winona is riding her Skarmory above the city.
Team Rocket is also at the carnival, and James laments the time he saw a Chimecho for sale at a carnival but did not buy it in time. Jessie and Meowth ditch him.
The kids meet Winona, and Ash challenges her to a Gym battle. She's busy with the carnival, so their battle will have to wait. Ash and friends decide to have fun, and release their Pokémon so they can have fun too.
James sees a Chimecho for sale—from the Magikarp salesman who's scammed him three times in the past! He buys it anyway, but once he shows it to Jessie and Meowth, it turns out to be just a Hoppip in disguise. A real Chimecho floats by, and happily joins James.
Ash and Winona arrive at the Gym, but an explosion in town calls them back to the carnival. Team Rocket is using a giant robot to shock and capture Flying-type Pokémon. When Ash fights back, they capture his Pikachu and Swellow too, and use Chimecho to heal their wounds.
Winona's Skarmory defeats Team Rocket with a Drill Peck attack, sending them blasting off. The festival resumes that evening, with the skies full of Flying Pokémon.
Ash and his friends are on the way to Fortree City in pursuit of Ash's next Gym battle and Badge. As the city comes into sight, Max notes that Fortree City has an abundance of treehouses, and Brock courteously explains that it's an old tradition in the city. Ash, on the other hand, isn't particularly interested in the trees and speeds off towards the Gym. Upon arrival, Ash calls out that he's here for a battle, and he's greeted by the Fortree City Gym assistant, Zachary. Zachary informs Ash that the Gym Leader is in the village, and unfortunately she's busy with the Feather Carnival, a once-a-year celebration of the sky in the city. Of course, Ash races down to the square to find the Gym Leader. While looking around the square, Max spots a Skarmory flying with two people, a woman and young child, on its back.
Ash and his friends move to track down the landing Skarmory. After a joyride, the Skarmory has landed and its Trainer is looking for another passenger to take on a Pokémon ride. Brock gets to her first, but Ash fights his way through the crowd and introduces himself to the pilot, Winona. They discover quickly that Winona is also the Fortree Gym Leader, so Ash immediately challenges her. Winona accepts the challenge, but delays the match until after the festival. That leaves Ash and others fairly idle for some time, so the friends calls out their Pokémon to enjoy the carnival. May and Max even get a ride on Skarmory like the other children, their first experiences on a flying Pokémon. Brock and Ash watch from the ground, discussing a combination of local history and strategy for Ash's upcoming match.
Team Rocket also arrives in Fortree City. Jessie and Meowth are perfectly happy to be at a carnival, but James seems rather unhappy. When pushed, James regales them with a story from his youth—when he was just a young boy he saw a rare Chimecho, which he wanted very dearly. Unfortunately, his parents wouldn't let him have one, and by the time he escaped his home to find Chimecho himself, the carnival had packed up and left. James says that this incident left him a "hollow shell of a man", and bursts into tears. However, it turns out that Jessie and Meowth got bored and walked off while he was talking, despite his emotional display. James later forgets that his teammates ditched him when he passes a stand selling Chimecho. He is immediately apprehensive as the swindling Magikarp salesman is running the stand, but James is conned into buying one of the "Chimecho" with the trio's remaining money. James walks away happy, thinking that his new "Chimecho" will bring him success and happiness. Jessie and Meowth soon find James, and are quick to point out that it's not a Chimecho—it's in fact a Hoppip painted like a Chimecho with a bell for a tail. However, just as Jessie and James begin to fight over the error, a breeze whistles through and the Hoppip happily floats away. James's upset is quickly remedied when a real Chimecho floats by. James asks Chimecho if it would like come along with him, and Chimecho happily agrees.
Elsewhere, Zachary and Winona lead Ash up to the Fortree City Gym, an open arena on top of the Gym itself, on level with the surrounding trees. Before Ash and Winona can start their battle, an explosion breaks out in the city square below. Team Rocket, in their new Double Trouble Sparky Shocker mecha uses electricity to disable and capture all of Fortree City's famous flying Pokémon. Winona and Skarmory immediately hit the robot with a Steel Wing. Team Rocket launches into their motto joined by Chimecho, then the battle commences. Pikachu uses the Thunderbolt on Team Rocket, but Chimecho uses Heal Bell, which replenishes the trio's health. Ash opts for another strategy, and has his Swellow fly in with Pikachu on its back. Swellow pushes through the mecha's electric attacks before getting close enough to retaliate with a Wing Attack. However Team Rocket counters with another electric attack and capture Swellow and Pikachu. Skarmory, however, uses a Drill Peck attack to break the robot's cage and free the captured Pokémon. Skarmory Drill Pecks the robot, and the resulting explosion blasts Team Rocket off. While the day has been saved, the sun is setting, so Ash and Winona agree to delay the battle until the following day. The day and the Feather Carnival end with a fireworks display and some formation flying, with Winona at the head.