Christopher Robin and his friends make a Christmas list, but Pooh forgets to ask for a present. He must get the letter back, and get it to Santa Claus by Christmas, which happens to be tomorrow.

Piglet faces his Halloween fears in order to be able to celebrate Halloween with Tigger, Eeyore, Gopher and, of course, his best friend Pooh Bear.

It's Thanksgiving time in the Hundred Acre Wood and Winnie the Pooh and his friends bring food for the big dinner. Piglet brings 'haycorns,' Pooh brings honey, Owl brings biscuits, and Tigger brings ice cream. But things change when Rabbit informs them that Thanksgiving is a special time of year that should include special items, so Pooh and the gang set off to find those very items.

When Christopher Robin is seen writing a Valentine note to a girl, Pooh and the gang fear that he has been bitten by a "smitten".

Pooh and his friends gather together on Christmas Eve to remember a past Christmas (Winnie the Pooh and Christmas Too), and then make New Year's resolutions to try to keep an annoyed Rabbit from moving away.