Ojo is excited about a visit from her friend, Christine. The two quickly get involved in one of Ojo's imaginative games --- a pillow castle. Tutter arrives and asks if they'd like to play checkers, but Ojo tells him she's in the middle of her game with her "best friend," Christine. Tutter is hurt by the use of the term "best friend." He creates his own friend to play with, "Mr. Cheese," but Bear helps to mend his friendship with Ojo. He also finds Pip and Pop at odds with Treelo out at the Otter Pond. He keeps pretending to be a monster during their Deep-Sea Divers game and they don't like it at all. Bear, however, introduces them to a game called The Treasure of Kalamazoo Bay. In the Shadow segment, Shadow retells the story of "Mary Had a Little Lamb." The lamb in this version drives a car, skies and scuba dives in its efforts to follow Mary everywhere she goes.

It's Halloween at the Big Blue House. The house is all decorated and everyone is getting ready. Bear helps his friends to find costumes and helps Tutter with carving a pumpkin. He always helps out Treelo when he's scared by Ojo's bat costume. Later, everyone gets together for some fun trick-or-treating. The kids have all picked out their Halloween costumes, but Bear hasn't been able to find anything to dress up as. The kids go through Bear's box of costumes and come up with an amusing idea. In the Shadow segment, Shadow performs the song "What Do Shadows Do for Halloween?"

One morning, Bear finds that he can no longer do The Bear Cha-Cha-Cha. It seems that he has simply lost his rhythm. It's so bad that he can't even say "cha-cha-cha." He loaned his records to Doc Hogg, but when he can't get them back, he has to find some other way to regain his rhythm. Pip and Pop attempt to help by providing their services as the "rhythm-masters." Later, Bear finds Treelo dancing to a calypso beat and joins in. In the Shadow segment, Shadow sings a song called "Tingalayo." About a donkey, it featueres a Latin beat. She also gives Bear a tip to help find his rhythm. Songs Rhythm in the Air Let the Rhythm Take You You've Got the Rhythm The Bear Cha-Cha-Cha (Shortened Version) Notes Portions of the events of this episode were adapted for the book Time to Cha-Cha-Cha!.

Bear, Tutter, Treelo, Ojo, Pip and Pop have just had a sleepover and now Bear is waking up in the morning. It's still early, but the sun's about to rise and then everyone will be getting up. Some rise faster than others --- for example, Ojo finds all the morning noise upsetting at first, but given just a bit longer to sleep, she's good to go. Bear gets everybody going with a good breakfast. Treelo wants to run and play, but Bear helps him to appreciate that breakfast will give him the fuel to do that. Then, fueled and ready to go, they head for the events of the day. While Tutter, Treelo and Ojo go out flower-sniffing, Pip and Pop decide to go riding in their inner-tubes. When Pop can't find his, they all help to tidy up the house in an effort to find it. Bear then settles down to read a book, but not before the Shadow segment. Shadow sings a song about the morning, featuring a newspaper-fetching dog and sweetly-mooing cows.

The annual Tutter Family Reunion is held at the Big Blue House. Everyone works hard to get ready for this big occasion featuring Tutter's huge family. Notes Tutter's relatives include Grandma Flutter, Uncle Tito del Tutter, Tardy, Grandpa Highland McTutter, Whiner, Shouter, Jim and June. This episode was adapted in book form as The Tutter Family Reunion.

As the viewer arrives, Bear decides to try something a little different --- he wants the viewer to sniff him! It turns out that Bear's idea may have been prophetic because some very different things are happening around the area of the Big Blue House. Pip and Pop were out playing by the Otter Pond when they found something they've never seen before --- something with wings hanging upside-down from a tree. Bear explains to them that it's a bat. He tries to tell them all about it, but they disappear in a flash. Bear returns to the Big Blue House, where Ojo and Tutter both express the same sentiment. They're scared of the bat and don't want to have anything to do with it. Things only get worse when they all sit down and talk about it. Bear, however, meets the bat, whose name is Benny, and asks everyone else to meet it too. They reluctantly agree and find that not only is he not like what they expected --- Treelo is already his friend!

Doc Hogg is remodeling his office, so he asks Bear to hold some of his stuff at the Big Blue House for a while, including his computer. He also gives Bear permission to use it, so he shows Tutter and Ojo how it works. They learn that computers are interactive and that interactivity isn't something that can just be done with computers --- just doing something as simple as talking with someone is interacting. At first, they're reluctant to use the computer, but are soon having fun with it. As it turns out --- Pip and Pop already know about interactivity --- Pip shows Bear how much fun it is for him to interact with Pop, as opposed to something like a rock. Bear takes a crack at solving the daily puzzle, with the help of Treelo. In the Shadow segment, Shadow introduces the viewers to Gus, an "interactive shadow-dog" who's looking for his friend Gloria.

Doc Hogg stops by the Big Blue House to collect for charity. He's collecting for muskrat relief following recent flooding that left many of them homeless. Bear is completely out of money, so Doc Hogg agrees to come back later. Bear and Ojo then find Tutter struggling to cram an excess of stuff into his mousehole, giving Ojo the idea for a yard sale. The idea takes off and Pip and Pop are assigned to be sales-otters. Treelo finds some things of his own to sell and Ojo helps out by painting pictures. Tutter, however, finds it difficult at first to part with some of his things.

It's Thanksgiving at the Big Blue House, and Bear is preparing his annual feast. There are all sorts of delicious food, and Grandma Flutter and Doc Hogg are coming over to join the celebration. Everyone is very thankful for Bear's great feast, but Ojo wonders if there isn't more she can do to help. She becomes a sort of Thanksgiving commander and takes charge of the decorations and the Thanksgiving pageant. Ojo wants everything to be perfect, but soon finds things going outside her control. When it seems like all is ruined, Bear provides some reassuring thoughts on what the holiday is really all about. In the Shadow segment, Shadow tells the story of the very first Thanksgiving. Songs "So Much to Be Thankful For" (Bear solo and Full Cast versions) "Thanksgiving with My Friends"

Ojo is sleeping over at the Big Blue House. Bear helps get ready to go to bed, tucks her in and aids her in "surfing off to dreamland." Ojo falls fast asleep. Bear thinks of getting some sleep himself when he hears a knocking at the back-door. It turns out that Jeremiah Tortoise and Doc Hogg have arrived for an exciting card game of Go Fish. Jeremiah brought the cards --- special cards that actually contain pictures of fish --- but Bear hasn't even put out any snacks. He has totally forgotten that their game was scheduled for tonight, and now all the noise threatens to wake up both Tutter and Ojo. Sure enough, Tutter shows up, saying that he needs a drink of water. Bear tries to attend to Tutter's needs, while keeping his attention on the card game 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.

Continuing from part one 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' conversation and suggests making something. In the Shadow segment, Shadow sings a song about a Hanukah 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. 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 -- a peaceful, happy holiday in a warm house with good friends. Later, the search for the winter berry proves fruitful for all.