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. After hearing a howling noise, the group takes in an old hound named Jack with no home and invites him to stay for the holidays. This gets everyone thinking about the true meaning of the holidays. 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 "It's Kwanzaa Time".
In the second part of the Berry Bear Christmas special, the entire gang (now with Jack) goes out caroling. As the kids settle down to try to figure out what to do about a Christmas present for Bear, Bear turns his attention to the finding of the winter berry. Jack overhears the kids' conservation and suggests making something. Everyone enjoys their presents, but they worry that they've left out Jack. Jack helps them to see that they've already given him a gift. Later, the search for the winter berry proves fruitful for all. In the Shadow segment, Shadow sings a song about a Hanukkah dreidel. She then wants to give Bear a present, but says there isn't much a shadow can give a bear. So she has him kneel down and she gives him a kiss.