It's Tutter's birthday and viewers are invited to join Bear and the gang in the Big Blue House as they work together to plan a surprise party for Tutter. This stage production features many of the voices from the show and many of its songs as well.

The winter holidays find Bear and his friends planning a big celebration. They're all getting ready for Christmas, but also learn about Hanukkah and Kwanzaa. Bear also celebrates his favorite tradition, the finding of the winter berry. As things start out, Pip and Pop have put together a reindeer wreath. Everyone wants to help out with the wreath, so Bear suggests they all add something of their own. Later, the group meets Santa Hogg and presents him with a large list of holiday wishes. Then there's a bit of an argument when Treelo wants to open everyone's presents and not just his own. In the Shadow segment, Shadow thanks Bear for his gift of a scarf --- Shadows don't get cold, but it's the thought that counts. She then sings the song "It's Kwanzaa Time." After hearing a howling noise, the group takes in an old hound named Jack with no home and invites him to stay at the Big Blue House for the holidays. This gets everyone thinking about the true meaning of the holidays.