Kids can feel ready for school with Spookley the Square Pumpkin. This fall, Spookley stars in an animated music video for his song “First Times.”

In this video, kids can understand that first-time experiences can be fun, even if it seems scary. “First Times” will debut on Disney Junior, DisneyNOW, and Disney Junior’s YouTube channel on Sept. 5. 

To celebrate the music video’s debut, Holiday Hill Farm is holding giveaways where grand prize winners will win a visit from Spookley. Contestants can also win other prizes, like first-edition Spookly movie books, a Spookley Tonie figurine, first-edition cake toppers, and a Spookley plush. Educators and families can enter the contest before it ends on Sept. 30 by visiting

“First Times” correlates to the Holiday Hill Farm book, Spookley the Square Pumpkin, The First Day of School, which explores how Spookley deals with being in a classroom for the first time. This book is available for $9.95 exclusively at Barnes & Noble

Kids can spend time with Spookley by attending upcoming fall events. Spookley will make an appearance at Toy Fair in New York on Sept. 30. The square pumpkin will also appear at Sesame Place and Sea World for Halloween events, as well as Barnes & Noble for family-friendly events. 

This fall, kids can embrace new beginnings with Spookley the Square Pumpkin. To learn more about Spookley and his fall adventures, visit

About the author

Taylor Battle

Taylor Battle

Taylor is an editorial intern for Adventure Media & Events, writing content for The Toy Insider, The Pop Insider, and The Toy Book. Between reading fantasy novels and re-watching Disney classics, she can be found building houses in The Sims 4. Taylor is passionate about creating and is always looking to try new things.