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.

The Super Squad pulls out all the stops when they learn some devastating news involving one of their own. Alaric turns to Sheriff Mac for help getting some timely affairs in order.