10 years has passed since Princess Luna made her first return to her first 'Nightmare Night', after being freed of her evil 'Nightmare Moon' persona. Since that night, she happily visits various locations aside from Ponyville to double the fun in bringing fear to her loyal subjects.

However, Ponyville was the one community that Princess Luna never returned to for Nightmare Night. It wasn't because she hated the ponies there, it was just because she had to be 'fair' and bring playful harmless fear to different pony communities across Equestria once per year, for a full night. And as fun as it is, Luna feels that something is missing. Something about Nightmare Night that made her happy, isn't 'there'.

One night, Princess Luna gets a nice visit from a subject that she's quite fond of...only NOT the way she expected.