
The Horseland gang is excited to go on the Twilight Trek, an annual outdoor campout during the course of which horses and riders are expected to bond. Calypso has a saddle sore, however, that prevents her from being ridden. Chloe, who is also unable to go due to a cold, offers to let Molly ride Chili instead. The two initially don't get along, but become friends after a close encounter with a bear.
When Alma discovers that her pen pal, Alexander, is going to visit Horseland, she's worried that she won't be good enough for him. Chloe and Zoey attempt to help her prepare to impress him, but their plan backfires. The two end up making amends and becoming friends at the end of the episode, after a landslide endangers Alexander.
When a new boy, Jesse, comes for an extended visit to Horseland, Bailey is overjoyed to have a boy his own age to hang out with. When he starts neglecting his friendship with Alma, Molly, and Sarah, though, tension grows. Chloe and Zoey, always jealous of his relationship with the other girls, go out of their way to ensure that much of his time is spent with Jesse. When Horseland is chartered for the Birthday party of the annoying Ethan Simon, though, the friends must get back together to organize the party.