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Applejack and her friends deliver an apple tree to the foundling frontier town of Appleloosa. They find that the ponies of the town are in conflict with a nearby buffalo tribe, who have previously used the land set aside for the apple trees as a running ground for them. Twilight and her friends work to establish peace between the two sides, but Pinkie Pie's song, performed at an inappropriate time, leads the two sides to declare war on each other. The buffalo charge at the town, who fire on the buffalo with apple pies. When the buffalo chieftain (Scott McNeil) is hit with a pie, he discovers the pie is tasty and quickly puts an end to the battle. The two groups agree to an amicable solution: the ponies leave a trail for the buffalo to run through the apple grove, while the buffalo get to enjoy apple pies made from the fruits.

Princess Celestia visits Ponyville along with her seemingly sick pet bird, Philomena. Fluttershy, worried about the bird's health, secretly takes Philomena to her cottage and tries to help her, but everything she does seems to worsen the bird's condition. When Twilight discovers this, she gets involved in helping cure Philomena, and learns that the Princess's guards are looking for it. Eventually Philomena escapes, leading Twilight and Fluttershy on a chase through town. The chase ends when Philomena falls from the top of a statue, bursting into flames and falling as a pile of ash into Fluttershy's hooves just as the Princess arrives. Fluttershy profusely apologizes, ready to take any punishment, before the Princess reveals that Philomena is a phoenix. Philomena rises from the ashes as a powerful bird, and at Princess Celestia's insistence, apologizes to Fluttershy for having fun with her. 

Apple Bloom, Scootaloo, and Sweetie Belle, believing they can determine how to get their cutie marks by learning how the older ponies in town got them, seek out and learn how Rainbow Dash, Fluttershy, Rarity, Applejack, Pinkie Pie, and Twilight Sparkle earned their cutie marks. The six friends realize that Rainbow Dash's first Sonic Rainboom triggered events by which each of them got their cutie marks, and realize they are closer than they originally thought.

Twilight realizes that Spike, being a baby dragon, is unable to stay awake to help her with her astronomy studies, but finds help with a new pet owl, Owlowiscious. Spike becomes jealous of Owlowiscious, thinking the owl wants to replace him as Twilight's assistant. Later, Twilight finds a book damaged by Spike's fire breath and scolds him for hiding it from her, and later still expresses disappointment when he tries to frame Owlowiscious for killing a mouse. Convinced Twilight no longer wants him, Spike runs away from home and finds a cave full of gems. He realizes too late that the cave belongs to an adult dragon, but Twilight and Owlowiscious soon arrive and save him. Twilight admits to Spike that she only needs Owlowiscious for additional help at night, and the two reconcile while Spike makes friends with Owlowiscious.

After throwing a birthday party for her pet alligator Gummy, Pinkie decides to throw a day-after party to continue the celebrations. She finds that her friends all seem to be busy. Suspicious of their behavior, Pinkie follows her friends and discovers that they are actively avoiding and hiding something from her in Applejack's barn. Pinkie becomes depressed, thinking the five no longer consider her a friend. She throws her own party using inanimate objects when Rainbow Dash retrieves her and brings her to a party at the barn. Pinkie thinks her friends are throwing a party to get rid of her, only to realize it is actually her own birthday party, which she had forgotten. Pinkie quickly becomes elated and joins the celebration with her friends.

The night of the Grand Galloping Gala in Canterlot has finally arrived. At the Gala, Twilight and her friends quickly separate to enjoy the Gala in their own ways, but each soon finds their experience fall well short of their expectations. As events mount, the friends' actions lead to a mass of chaos in the grand ballroom. They regroup later at a donut shop and express their disappointment with the night's events, but are soon joined by Princess Celestia, who explains that she had invited Twilight and her friends to liven up the normally boring Gala, and is happy with what happened. Everyone agrees the night to be the "best night ever".