The series takes place after the events of Milne's original stories since his son Christopher Robin is clearly an 11 year old.

For example, Tigger resides in the Hundred Acre Wood from the start, and Kanga and Roo are later introduced as newcomers.

Kessie, the bluebird from The New Adventures of Winnie the Pooh episodes "Find Her, Keep Her" and "A Bird in the Hand", returns as a main character in this series.

The characters in the show regularly sing and dance in ways that enhance the story being told.

Roo sets out on a Christmas Eve adventure with Pooh, Piglet and Tigger in search of a tree that grants wishes, while Rabbit follows a magazine's step-by-step instructions for the perfect holiday party.

The film was produced by Shadow Projects, distributed by Buena Vista Television, and released on both VHS and DVD.