When things take a dark turn on the twins' 17th birthday, Lizzie is left to make a difficult decision. Meanwhile, Hope takes drastic measures when she and Alaric clash over how to handle an issue involving Josie. Finally, Rafael makes a heartbreaking discovery.

In a race to save Josie, Hope infiltrates her subconscious and finds herself in a fairytale world filled with dark magic. Back at the Salvatore School, Alaric, Lizzie and the Super Squad commit to their own risky plan to get Josie back despite the potential consequences.

In order to get a handle on some urgencies at the school, Alaric sends the students off-campus for their first-ever field day. But when a medieval monster arrives with a challenge, the students are left scrambling to guess which one of them may be a worthy opponent.