Twenty-five years ago Quirin and a warrior named Adira once served King Edmund of a Kingdom that was consumed by the Black Rocks. The King hopelessly tried to destroy the Opal, which is believed to be the causation of the rocks, to no avail. After many failed attempts, King Edmund advised Quirin and Adira to leave the castle and keep anyone from ever finding the opal. In the present, after ending Varian's reign of vengeance, Rapunzel is out on the road with her friends. It has been a week since she left Corona, and is excited to be on her first trip beyond the kingdom walls. Accompanying her on her journey are Eugene, Cassandra, Pascal, Maximus, Fidella, Owl, Lance, and Hook Foot. Together they ride through the country in a large colorful caravan, following the trail of the Black Rocks.
Meanwhile, Eugene is in the caravan speaking with Lance and Hook-Foot. He is planning to propose to Rapunzel again when they reach Vardaros. He is confident that he will succeed this time, but Lance and Hook-Foot have their doubts. They are not so sure that Rapunzel is ready to settle down with him, especially since she is out free in the world for the first time in her life. Soon, the caravan comes to a stop. Lance and Hook Foot go looking for a picnic spot while Eugene remains in the caravan rehearsing his proposal. Listening in against the door, Rapunzel accidentally catches him on his knees presenting an engagement ring. Both feeling awkward, Eugene tries to convince Rapunzel that he was not asking her to marry him. Just then, they hear a strange scream. Cassandra found Shorty stowed away in the food trunk. He fell asleep and ate all their supplies.
The group finally arrives at Vardaros, which appears to have become, much to Eugene and Lance's shock, a sketchy rundown city crawling with shady people. Everyone decides to keep a low profile while in town. Rapunzel and Cassandra take the caravan back to the campsite while Eugene, Lance, Hook Foot, and Shorty collect the supplies. Pretty soon, people in the shadows take notice and recognize Eugene. News of Eugene's arrival is quickly spread throughout the city and reaches a castle homed to the notorious kingpin known as the Baron. Anthony the Weasel is keen to dispose of him, but the Baron wishes to settle things with Eugene personally. In town, Eugene, Lance, Hook Foot, and Shorty are on their way back to the camp with the supplies, when a girl calls to them that Rapunzel is in trouble. They follow her and become surrounded by the Baron's men. They are greeted by the Weasel, who paid the girl, known as Vex, to lure them into their trap.
Meanwhile back at the campsite outside the city, Rapunzel and Cassandra discuss Eugene's proposal until they are interrupted and are met by Adira who wishes to have a private chat with Rapunzel. Cassandra does not trust her and stands in her way. Despite not wanting to fight, Adira reluctantly engaged the two girls in a duel. She easily and amusingly fights them off and disarms them. The fighting does not stop until Adira discovers the nature of Rapunzel's hair when she fails to cut it off her wrist with her black rock bladed sword. Just then, Hook Foot shows and Adira leaves, promising to seek them out later. He had just escaped from Weasel's men and tells Rapunzel that Eugene has been captured along with Lance and Shorty.
At the Baron's castle, Eugene, Lance, and Shorty are brought before the Baron and his daughter, Stalyan, who is also Eugene's ex-fiancée. Long before Eugene met Rapunzel, he was engaged to Stalyan until he stood her up at the altar. Afterward, Stalyan swore that if she ever saw him again she would break every bone in his body, but after a while, she got over it and realized they were still meant for each other. The Baron offers Eugene a proposition, keep good on the promise he made to his daughter and marry her or suffer painful consequences along with Lance and Shorty. To get his point across, the Baron allows a venomous spider to bite Lance. Unless Eugene marries Stalyan, Lance will die from the spider's venom within hours if he is given the antidote in time.
Rapunzel, Cassandra, and Hook Foot arrive back in town looking for Eugene. They go around asking people, but nobody is interested in helping them find their friend. This makes Rapunzel infuriated. Pretty soon, they heard a commotion. The Baron is announcing Eugene and Stalyan's engagement and upcoming wedding to the citizens of Vardaros. Waiting backstage, Eugene attempts to convince Stalyan not to go through with this plot to no avail. Eugene refuses to go through with the engagement and confesses he is already in love with someone else. Surprisingly, Stalyan is already well aware of Eugene's love for Rapunzel, including their history when he rescued the lost princess from her tower. However, Stalyan begins to make Eugene doubt his relationship with Rapunzel, questioning is it right for her to give up her newfound freedom for a life with Eugene, saddening him. Shortly after, Stalyan goes on stage to make her appearance and soon after the Baron introduces Eugene as her fiancée, shocking Rapunzel, Cassandra, Pascal, and Hook Foot. Rapunzel approaches the stage, demanding an explanation. Eugene tries to speak with her, but Stalyan interrupts him, revealing he has joined them. Rapunzel refuses to believe Stalyan's claims, but Eugene seeing Lance growing more weaker is unable to reveal the truth to her. He simply apologizes and states he has made his choice. Eugene then leaves alongside Stalyan, leaving Rapunzel heartbroken.
Back at the Baron's castle, Stalyan visits Eugene in his prison cell. Eugene once again pleads for her to call off the wedding and give him the antidote to save Lance's life. Stalyan ignores him and instead simply reminisces about their past together and reveals her personal thoughts that Eugene belongs with her. Stalyan also makes him feel that, once again, by wanting to marry Rapunzel, he’s only taking her desired freedom. She soon leaves to prepare for their wedding, leaving the keys on the ground by the door. Back at the camp, Rapunzel is still heartbroken by what Eugene has done, unaware that he is being forced into marrying Stalyan. She recalls the first time he asked her to marry him and wishes she could take back what she said before. Cassandra comforts Rapunzel. Despite being disagreeable towards each other, Cassandra has known Eugene long enough to know that he truly loves Rapunzel and would never do something like this to her. Helping her regain her spirit, Cassandra encourages Rapunzel to rescue Eugene.
With some help from Vex, Rapunzel and her friends sneak into the wedding just as the ceremony is about to begin. They find Eugene waiting at the altar as Stalyan walks down the aisle with her father. The Baron begins to officiate the wedding but is interrupted when Rapunzel reveals herself and declares her love to Eugene. Rapunzel touches the Black Rocks, intending to releasing their power, but to her surprise and confusion, nothing happens. A fight soon ensures between the Baron's henchmen and Rapunzel's friends, including Adira who later joins in and reveals the reason why rocks no longer react to Rapunzel is because they have found the Sun Drop. Stalyan attempts to escape with a captive Eugene, but Rapunzel prevents her. Both Rapunzel and Stalyan then engage in a tug-of-war with Eugene at the center. Pascal creates a distraction by startling Stalyan, setting Eugene free from her grasp. The Baron engages in battle with Eugene and successfully pins the latter down. As he prepares to unleash his Kai spider, Shorty's clumsiness causes the spider to bite the Baron instead. Fatally wounded, the Baron desperately searches for the antidote, but it had already been stolen by Pascal and used to cure Lance. The Baron, nevertheless, accepts his oncoming death, and tries to strike Eugene down in vengeance, but is thwarted by Rapunzel. With the battle over, the Baron and his henchman are forced to flee. Stalyan carries her injured father and leaves, but not before informing Eugene she will someday settle things between them once and for all, leaving a happily reunited Eugene and Rapunzel behind.
Rapunzel starts to discuss Eugene's second proposal. Realizing how much she truly loves Eugene after almost losing him to Stalyan, Rapunzel begins to reveal her decision to say yes. However, finally realizing and understanding Rapunzel's desire and need for freedom, Eugene decides to hold off the proposal and marriage again and give her more time until she is truly ready. Rapunzel pretends that’s just what she was thinking and agrees to it, but discreetly shows signs of disappointment. Nonetheless, Rapunzel and Eugene are happy to be together again and seal their reunion with a kiss. The next day, Rapunzel meets Adira again and reveals herself as an ally and friend to help guide Rapunzel on her journey to her destiny. Adira shows Rapunzel the remaining part of the ancient scroll and reveals the rocks are guiding her to the Dark Kingdom. Eugene appears and assures they will make it on their journey and will reach their destination together. Adira leaves and watches from afar as Rapunzel and her friends get back on their journey.
- Mandy Moore as Rapunzel
- Zachary Levi as Flynn Rider
- Eden Espinosa as Cassandra
- Yvonne Strahovski as Stalyan
- Lance Henriksen as the Baron
- Gideon Emery as Anthony the Weasel
- Bruce Campbell as King Edmund
- Jonathan Banks as Quirin
- James Monroe Iglehart as Lance Strongbow
- Jeff Ross as Hook Foot
- Paul F. Tompkins as Shorty
- Kelly Hu as Adira
- Britt Robertson as Vex
- Ralph Ineson as Cutter
- Starting from this episode, Rapunzel and Eugene receive new signature outfits.
- Also, the opening theme is updated with new footage.
- Zachary Levi (as Eugene) and Yvonne Strahovski (as Stalyan) previously collaborated in the TV series Chuck.
- Rapunzel lost her ability to activate the power of the Black Rocks.