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.

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.

A once-wild horse named Puma comes to Horseland, and talks of his life in the wild. This makes Aztec also want to run away and be free. He sneaks away at night, but comes to find out that life away from civilization is a lot harder than he expected. Meanwhile, Bailey is distraught with worry for his beloved horse. Eventually, the two are reunited, and Aztec decides that he prefers life at Horseland. Meanwhile Sarah is at Stand Hope riding school but later decides to stay with her friends.

An elderly horse teaches Chili about a horse's innate herd instinct, a form of magic, and how it is beneficial for the whole group of horses.

While the other members of Horseland vie for a broadcast internship, competing fiercely with each other, Sarah tries to re-train Diablo, a stallion injured in a jumping accident for her friend Madison.

Over the course of a winter, the beloved barn cat of Horseland, Mosey, is becoming very old and sick. Seen through flashbacks, the tale unfolds of his increasing illness and eventual death. All the riders, animals, and horses, especially Sarah, are heartbroken by his loss, and have trouble coming to terms with it.

Chloe and Zoey blame Sarah when things start disappearing around the stables, and the tension threatens their riding teamwork for an upcoming important parade.

Zoey finds an injured bluebird in the Horseland Greenhouse. She tries to nurture it back to health, and forms a bond with it. Despite her attachment to the bird, though, she fails to see that keeping such a bird caged is bad for a wild animal.

n equestrian fashion designer comes to Horseland, and the gang is thrilled to model for the subsequent photo shoot. However, the clothes are impractical and too dangerous to ride in. The kids must speak up before someone gets hurt.

The Horseland gang goes on a trip to France for a riding exhibition. Sarah's father encourages her to befriend the daughter of one of his friends, an Indian girl named Simbala. Both girls worry that the other won't like them, and a few mishaps seem to confirm this. When the pair falls into an underground cave, though, they discover that they are more alike than they are different.

Alma,Chloe and Zoey strike a deal: Alma will be more competitive during an upcoming show jumping competition if Chloe and Zoey will be nice. When Alma has to face a rude super-competitive rider from Horseland's bitter rival, Stanhope Academy, though, she's not sure that being untrue to herself is such a good thing.

Alma accuses Molly of spreading malicious gossip about Sarah, even though it is not true. The friends become divided, and give Molly the silent treatment until the truth is revealed.