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".

Seasons of giving is a 1999 American direct-to-video Christmas animated musical film that included A Winnie the Pooh Thanksgiving, and the two episodes from The New Adventures of Winnie the Pooh ("Groundpiglet Day" and "Find Her, Keep Her") (these episodes take place during the first two seasons). It features a new song by the Sherman Brothers. Seasons of Giving was released by Buena Vista Home Entertainment on November 9, 1999.

On Christmas Eve, Winnie the Pooh is having trouble setting up his Christmas tree. Pooh slips and falls, and breaks a shelf holding a present he made for Piglet. When Piglet suddenly arrives, Pooh desperately searches for a new hiding place for the present (since the broken shelf can no longer stay up) as more of his friends arrive at the door, eventually hiding it in an empty honey pot before helping himself to a full pot of honey, but forgets to answer the door. Afterward, his friends, tired of waiting for Pooh to answer, invite themselves in and proceed to help decorate his house. At one point, Tigger annoys Rabbit with some jingle bells. After they settle down to tell stories, Rabbit tells how they almost missed out on getting gifts one year, re-telling the story of Winnie the Pooh and Christmas Too. Afterward, Pooh appears dressed as Santa and exchanges gifts with everyone.