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 students prepare to put on a musical about the founding of the Salvatore School at the behest of their mysterious new guidance counselor. Meanwhile, as Landon throws himself into writing the musical and Lizzie, Josie, Kaleb and Jed dive into their roles, Hope distances herself from the musical.