Our story begins with Jack Scarecrow in the Holiday Hill Farm Pumpkin Patch, looking at Big Tom, Little Tom, and Bobo, all pumpkins. He also notices the Honeydoos, a duo of singing melons. Jack is very excited for Halloween and begins dancing around the patch. ("It's Halloween")

Jack and the pumpkins hear a small voice, but don't know where it's coming from. Jack looks around the patch and discovers Spookley, a square pumpkin, under a large leaf. Jack is excited to find Spookley and tells him he could be the Pick of the Patch this year. The other pumpkins, however, don't like the fact that Spookley looks different from them. ("Look at Spookley") Jack tells the other pumpkins to be nice to Spookley and goes off to finish some other chores on the farm. Once he leaves, Little Tom insults Spookley and tells him that he is going to ruin Halloween for the rest of them because he is not a real pumpkin: real pumpkins are round. Spookley is left alone, and becomes very sad. ("If I Was Round")

Spookley worries that he will ruin Halloween for everyone. Suddenly, three spiders appear and introduce themselves as Edgar, Allan and Poe. They tell Spookley that he can't worry about what the other pumpkins say: plenty of spiders have been faced with challenges, but they believed in themselves and succeeded in the end. ("The Boo Song")

Spookley still isn't convinced; he remembers Little Tom telling him he's different. Edgar reminds Spookley that everyone and everything is different. Being different isn't a bad thing. Edgar tells Spookley he can be the Pick of the Patch if he sets his mind to it. ("I'm Gonna Try")

Meanwhile, the other pumpkins are getting ready for Halloween and all think they will be chosen as Pick of the Patch. Bobo is overconfident. ("She's Bobo") Spookley returns to the patch to everyone's surprise, but Little Tom makes fun of him and his new spider friends. Jack returns and lines everyone up for the Pick of the Patch. He says something nice about everyone and Bobo and The Honeydoos start singing. Suddenly, a storm starts up!

Everyone is blown around by the wind and rain toward the dangerous river, except for Spookley. He decides to help the other pumpkins and blocks a large hole in the fence with his body. The pumpkins and Jack are blown toward him and all pile up in front of the broken fence until Spookley cannot be seen anymore.

Spookley doesn't wake up for a few minutes, and every- one is worried, even the pumpkins that made fun of him earlier. Luckily, he opens his eyes and smiles, letting everyone know he's okay. Jack tells Spookley that he is quite the hero. All the other pumpkins apologize to Spookley for bullying him because of his differences; even Little Tom. They welcome him to the patch. ("The Transylvania Twist")

Farmer Hill arrives to choose the Pick of the Patch and picks...Spookley! He loves the fact that Spookley is square. Everyone celebrates Halloween together in the patch. ("I'm Gonna Try (Reprise)")