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 counsellor. 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.
After one of their own goes missing, Alaric suggests Hope turn to the therapy box, which thrusts her into a twisted game set in a summer camp slasher flick. Meanwhile, Lizzie's attempt to spend some time with MG doesn't go quite as planned, and Josie makes a big decision about her future.
After a sudden mass exodus of the school's student body, Alaric and the squad desperately try to recruit new students to keep the school afloat. Hope agrees to help Lizzie with the new student orientation. Josie enjoys a fresh start on her first day at Mystic Falls High, while MG begins his semester of "no".
Lizzie suggests holding a fundraiser for the school. Cleo helps Hope cope with her emotions. MG seeks help from Alyssa. When a leprechaun shows up at the school, it might be what they need to turn their luck around.