Raggedy Ann (June Foray) and Andy (Daws Butler) and their dog Raggedy Arthur noticed how cruel their neighbor Aunt Agatha (Foray) is and how sad her nephew Ralph (Steven Rosenberg) is on Halloween. The Raggedies at first, seem really annoyed with how Aunt Agatha treats her nephew and think that she's really mean to treat him in such a way. However, then they come-up with an idea on how to make Ralph happy. Raggedy Ann reasons that if there's an unhappy little boy where they live, than there must be an unhappy pumpkin somewhere out there waiting for a little boy. The Raggedies set out to find the pumpkin who's just right for Ralph. The abandoned pumpkin (Les Tremayne) is very gloomy and emits pumpkin seeds as tears every time he weeps. The only way to cheer up the sad pumpkin is to bring it to Ralph to give and then convince Aunt Agatha to change her ways on Halloween.