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.
The story continues in part two.
- Berry Bear Christmas
- A Holiday for Everyone
- That's All I Want for Christmas
- It's Kwanzaa Time
- What If (There Was No Big Blue House)
- Just Listen
- Shadow twists the format of the Shadow segment in this episode. Instead of Bear searching for her, she searches for him and sings "Where Oh Where is Bear?"
- The dog in the Shadow Projects logo in the closing credits says "Happy holidays!" in Treelo's voice, but only on the DVD version.
- Both parts of this special were adapted as the book Bear's Berry Christmas.
- Dave Goelz performed Jack in this double length episode.
- In "That's All I Want for Christmas," Pip and Pop ask Santa for "tons and tons of clams." It is revealed in the fourth season of the program that clams are a form of currency in Woodland Valley.
- This is the only episode where Bear does not say, "It's you!" after he sniffs the viewers.
- This is the only episode that does not use the Goodbye Song. Instead, Bear and Luna sing Just Listen.
- When the special aired on Playhouse Disney over two days, the first Shadow segment was cut, as well as Bear hanging the reindeer wreath on the door and then hearing the kids arguing.
- On the VHS version of the special, there are no closing credits shown --- instead, Luna is shown setting and Ray rising; the show continues immediately to the next part.
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