Fly Me to the Moon!

Plot
As Ash and his friends walk towards Bluefinland, Misty spots four Corsola, a Pokémon she desperately wants to catch for herself, swimming nearby. Brock reveals the Corsola are headed towards Pudgy Pidgey Isle, so Misty demands a boat to reach them. A local man, Wilbur, overhears the conversation and reveals that he can take the group across. He shows them to a rope bridge to avoid the swirling whirlpools below. Despite a strong gust of wind everyone makes it onto Pudgy Pidgey Isle. Afterward, Wilbur calls out and a flock of Pidgey come towards him for food. The Pidgey don't look normal, they are particularly chubby. Wilbur explains that these Pidgey have no natural predators because the island is protected by the whirlpools, and therefore they have no need to fly, hence their larger bodies. Team Rocket scopes them out from above, seeing that there could be another good catch for the day.

When they reach Wilbur's house, another Pidgey soars by them and lands on the roof. Wilbur says that's his special Pidgey, Orville. Wilbur explains that Pidgey were once used for delivering messages, but this service has been needed less because of modern technology like the videophone. They call up Professor Oak and he explains that the scientific community is very interested in the pudgy Pidgey and an ongoing debate is trying to figure out if they are a variation or evolution of Pidgey. He asks Ash to call him again if he notices anything new before signing off.

Orville flies into the home and gazes at a picture on the wall, which features several Pidgey flying towards the sun. Wilbur explains that his grandfather painted the picture based on a fairy tale. A while ago when Orville was still a fledgling, he became interested in that painting and set his sights on learning to fly. Wilbur helped Orville build up its strength every day. One day while Wilbur was training with Orville, he decided to hang glide towards the ocean and see if Orville was capable. Orville managed for the first few minutes, but couldn't keep up and started to lag down towards a whirlpool. Orville then noticed the sun, which reminded him of the painting and soon Orville was able to fly back up and with ease. Wilbur admits that Orville is wanting to reach the outer atmosphere, but he hasn't measured how far it can go yet.

Team Rocket, overhearing this, arrive disguised as meteorologists. They offer to assist Orville in reaching its goal free of charge, and propose using a balloon to monitor him. The deal seemed to be too good to pass up so Wilbur agrees. Team Rocket even invites Ash and his friends along to be witnesses, but this also a ploy to catch Pikachu. Later that night, Meowth approaches Orville, who is sleeping on the deck, and presents it with a headset so the pair can communicate as Orville attempts to reach its flying feat. Meowth admits that he wished he had the support when he learned to speak human speech, and the resounding speech encourages Orville for tomorrow's attempt.

The next day, everyone boards balloon and begin their ascent. James activates the rocket boosters, sending the balloon soaring to over 3000 meters. Meowth relays the conversations during the ascent directly to Orville's headset. As Orville makes a steep climb upwards, it rushes past a flock of Spearow only to anger them. The Spearow give chase, but Wilbur is sure that Orville will be fine. The balloon reaches 10,000 meters and the humans place oxygen masks on because of the increasingly thin air. A Fearow begins to pursue Orville, though Ash orders Pikachu to give it a Thunderbolt. Fearow falls out of the sky, but lands on the hot-air balloon and breaks the special skin, which reveals that it actual Team Rocket's Meowth balloon. Ash is instantly suspicious, and Team Rocket reveal themselves, but they put their scheme aside to focus on Orville. Soon they are so high up that even Meowth, Pikachu and Togepi, who didn't need the masks, now require some oxygen. The balloon then reaches its limit, and the rockets stop working, but Orville continues its ascent. Wilbur calls out to his friend, but Orville relays to Meowth that it wishes to continue soaring higher and doesn't feel a thing. Frost gathers on Orville’s body, and Meowth offers Orville his support because of his own struggles to conquer his goals. Orville reaches the outer atmosphere and admires the abyss of space for several moments, remarking that it can nearly touch the moon. It soon dives towards the world, but it is plummeting at a worrying speed. Orville follows Meowth's instructions and changes course for the balloon. Orville crashes through the balloon, and lands inside the basket. Meowth is quick to offer it oxygen, but Orville isn't responding. Everyone becomes increasingly worried as precious seconds pass so Pikachu gives it a jolt of electricity, and Orville comes around. Meowth brushes off a tear seeing that Orville is fine. Unfortunately the troubles aren't over yet, and the hole gets bigger. Everyone clings on as the balloon descends at a rapid pace. The pudgy Pidgey below notice this and begin to flap their wings. They get some height with their jumps and manage to tackle the balloon basket, breaking the fall. Everyone is fine, but one of the rocket boosters starts up automatically, sending Team Rocket blasting off.

Ash and his friends watch as the other Pidgey begin flapping their wings. Wilbur suggest that Orville has become a hero to the other Pidgey and reminded them of their desires to fly. As the sun sets, the group says their goodbyes and continues to walk towards Bluefinland. Meanwhile, Jessie and James are stuck hanging from a tree by their shirts. Jessie queries where Meowth is, and soon spots Meowth as he discusses the outer atmosphere with Orville.