Rapunzel journeys to the cottage of a healing wizard with Cassandra, where he asks the latter to tell Rapunzel to consider cutting her hair, to which she replies that it's impossible.
Rapunzel faces-off with an old man in a competition, she finds herself booed by everyone, whereas the man is showered with encouragement. This only fuels Rapunzel's drive for winning.
Eugene wants to find something to do within the castle so he decides on being a royal guard. However, he must work hard and sacrifice a lot to reach his goals.
Rapunzel is not interested in entering the Challenge of the Brave. That is, until Cassandra enters. Rapunzel then decides to join as well, and their competitive natures reveal themselves.
In order to get them to bond, Rapunzel locks Eugene and Cassandra together in the dungeon which forces them to work together to find an escape. However, it does not go as expected.
Strongbow, an old friend of Eugene, waltzes back into town and tries to lure him back into their old life as thieves. Eugene has to make a decision.
King Frederic seeks the help of Eugene to to help him pull off his elaborate schemes. Meanwhile, Rapunzel seeks to do something different in the kingdom.
Cassandra gets an opportunity to finally go on guard duty. However, she has to finish her tasks first. She then learns an important lesson.
Rapunzel learns that Cassandra has a new love interest, but it seems like the new crush might have a hidden motive. That's why Rapunzel decides to seek the truth.
Monty's Sweet Shoppe is ruined and Attila is accused. However, Rapunzel is the only one who believes his claims of innocence.
Pascal is alone and bored and feels like he has no purpose in Rapunzel's new life in the castle, so he decides to go away.
The kingdom is raided by infamous thieves who turn out to be two orphaned girls. In order to save them from a future in crime, Lance and Eugene help them out.
The snuggly duckling is haunted by its previous owner and Rapunzel decides to help the Pub Thugs in finding out what the ghost is after.
A new horse arrives in town to fight crime and Maximus thinks he found a new friend. However, he soon realizes this horse has ulterior motives.
Rapunzel discovers Queen Arianna's long-lost sister Willow and invites her to Corona. However, things don't go as planned.
The King and Queen take a trip to the mountains for their anniversary, and leave Rapunzel temporarily in charge in the castle. However, it's not as easy as it seems when she's responsible for making tough decisions.
After the blizzard, Rapunzel suffers from a self-confidence crisis. She decides to go back to painting and attends an art class.
Griffon of Pittsford is visiting Corona because King Frederic suggested a partnership between the two countries and everybody welcomes the new visitor. Rapunzel and Cassandra reunite on a new mission.
Rapunzel looks into a mysterious message from Varian, and ends up being chased by a group of masked men.
Rapunzel is furious at her father for lying about the Black Rocks. When Rapunzel's life is in danger, Varian intervenes and helps her decide her fate.
On Rapunzel's 19th birthday, the city falls into grave danger so the birthday girl herself receives several threats, and she has to take matters into her own hands.