Brother and Sister do some damage in Mrs. Grizzle's flower garden while retrieving their baseball. Instead of stepping forward to apologize, the cubs get nervous and run home. As fate would have it, Mama arranges for Mrs. Grizzle to babysit the cubs that very night. Brother and Sister anticipate a very stern talking to, but are surprised by Mrs. Grizzle's kindhearted manner.
On Halloween night, the cubs try to avoid Widder Jones's house, because Brother has heard rumors about her being a witch. As the cubs go trick-or-treating, they're afraid to get near her house for fear she'll turn them into statues. When the cubs realize Witter Jones is a nice lady, she and the cubs decide to play a trick on Too Tall and his gang (who give the cubs more rumors) by playing a trick on them.
Brother gets behind in his homework and Papa gets mad at him. Brother isn't allowed to watch TV, listen to music or anything until he gets caught up with his homework. Then Papa finds out that he needs to refile his taxes. With a lot of hard work, Brother and Papa both realize not to put things off. Instead of "procrastinating", they get right to finishing what's important.
When Brother gets a brand new three speed bicycle, Sister's envious feelings are personified in her dreams by a little green version of herself. This Green-Eyed Monster convinces Sister to sneak Brother's new bike out for a ride. But when she does, Sister realizes too late that it's too big for her and she can't control it. Fortunately, Brother and Papa rescue Sister before Brother's bike can crash. Together they help chase the Green-Eyed Monster away by jazzing up Brother's old bike and giving it to Sister.
When she adopts a baby chipmunk, Sister learns the hard way about trying to keep a non-domesticated animal as a house pet. As a baby, all the chipmunk does is eat and sleep. However, the bigger it grows the more active it gets, and the more mess it makes the more trouble it causes. Of course, none of it's intentional. That's just the creature's nature. But when it accidentally bites Papa, Sister finally realizes that if she really loves little Brown Eyes, she'll do what's best for the chipmunk and return him to the outdoors where he belongs.
When Mama casually mentions the "Star light, star bright" principle, Sister takes it to heart and wishes for a certain birthday gift and a better grade on her next math test. She gets both her wishes. However, when she wishes for a pony and it doesn't materialize, Papa helps Sister understand that she really got her first two wishes all by herself. She got her special birthday gift because she'd been so helpful around the house, and she got her better math mark because she studied really hard for the quiz. Bolstered by this, Sister makes her pony wish come true by making a deal with Farmer Ben to help him pick his peas in exchange for being allowed to spend time with his retired farm horse, Princess.
Brother and Sister think they're entitled to treats every time the family goes grocery shopping. Mama and Papa get tired of their "gimmie gimmie" attitude. When Gramps and Gran drop by for a visit, they tell a touching story that inspires Brother and Sister to change their selfish ways and start thinking about others in need.
Sister and her friends do not like gym because of all those exercises Teacher Jane makes them do. She remembers when Lizzie got out of gym by having an excuse note written for her when she sprained her wrist. When Sister is exiting the school bus at home, she trips on a rock and sprains her ankle. Mama writes her an excuse note, so Sister does not have to do gym. A few days later Sister is playing hopscotch and jump rope with her friends when teacher Jane sees her and gives the excuse note back to her. Sister is upset because her ankle got better. Brother tells Sister that gym can make her a better soccer player, so Sister decides to give gym another chance.
When Teacher Bob assigns his class a project on what they'd like to do when they grow up, everyone seems to know where their interests lie except Brother. After exploring Bear Country to see what types of jobs there are, Brother discovers he's interested in many things. Now his problem is deciding which one to include in his project. Finally, Brother decides to include all his job ideas in his report.
Sister wants to join the girl's soccer team, but Coach Brown thinks she's still too young to take part because the cubs are bigger than her. Sister grudgingly accepts the position of team manager instead. It's a tough job, and Sister's perseverance doesn't go unnoticed by the coach, who ultimately invites her to play in a big soccer match when a team member goes home sick.
Sister has a problem, she keeps biting her nails. The family thinks of many ways to make her stop. The real reason is fractions are making her nervous.
Papa bear is growing a giant pumpkin for the pumpkin contest on Thanksgiving day. He becomes obsessed with it being bigger than farmer Ben's and winning the contest. Farmer Ben himself has won the contest 10 years in a row. At the contest, Papa wins third place. Ben tells him 3rd place is good for a first time entry.
After watching a video at Lizzie Bruins house (Trouble at big bear high) Sister learns a new word ""Fur-ball"". After saying it to Lizzie and hers friends they leave. Also she says it to Brother after he tips her milk glass. After getting in trouble she See's Lizzie and mend their friendship with their friends.
Lizzie has a lot of Bearbies and wants to give her extra Golden Furred Bearbie to Sister. Lizzie's mom says "Some bears have big ears," and Lizzie replies "You mean Sister has big ears?" Sister thinks she really has big ears and becomes very self conscious about them. She and Mama go to the fair and go into the House of Mirrors. Sister realizes that bears come in all different shapes and sizes. When they get back home, Lizzie tells her that she didn't mean to say Sister has big ears. It's just that she didn't want to spoil the surprise.
Things get busy around the tree house. Sister, Brother, Mama, and Papa all have things to do! After an incident in which everyone brings the wrong stuff to the wrong places, Papa and the family put up a calendar on a wall to show who has certain appointments to get to. The first time they use the calendar, it gets filled up completely! After a restless night where everyone has dreams about the calendar, it's another pressure-filled day! When Mama can't get the car to start, everyone breaks down in complete tears! The Family re-does the calendar and everything becomes A-OKAY!
Mama gets free tickets to go to Fun Park. Freddy and Brother say they are not afraid of riding the rollercoaster. Lizzie and Sister admit that they really are afraid. Brother doesn't want to ride the rollercoaster and admits he was afraid, so he and Freddy don't ride it. Papa was in line with them and accidently boards it.
It's Grams and Gramps anniversary. Papa and Sister try to find the perfect fishing spot to catch the perfect fish. Meanwhile, Brother and Mama are picking berries for the perfect dessert. After both pairs have many problems, including Little Lady eating the berries and Papa getting caught in a fishing net, they decide that they don't need the "perfect" anything to celebrate Gram's and Gramps's anniversary.
When Brother and Sister are bored on the first day of Summer Vacation, Farmer Ben invites them to work on the farm with him. The cubs are excited by the news, but are later disappointed to discover how much work it entails. However, they also learn that hard work pays off!
The Bear family is going on a mountaintop vacation for an entire week. Papa hopes for it to be the best vacation ever. During the week, nothing goes right for Papa. His fishing hook gets caught in the weeds, the boat sinks, the Bears pick sour berries, and their cabin gets flooded during a rainstorm at night. Papa gets frustrated when their vacation is turning into the worst one ever and wants to leave ASAP! Mama and the cubs show Papa pictures they took of him when nothing went right for him, and they show him how to look at things in a different way. Papa realizes that he had been looking at everything on the dark side all along, and the Bears' vacation goes from the worst to the best.
The cubs' younger cousin, Honey, is apprehensive about going to the doctor's office for her first checkup. Sister dispels Honey's fear of the unknown by setting up a pretend doctor's office and taking Honey through all the procedures of a checkup, using the instruments that are in her toy doctor's bag.
Looking for something to do their environmental school project on, Brother and Sister visit Professor Actual Factual at the Bearsonian Institute. Not only do they discover that too much trash in Bear Country is a big problem, they also learn about endangered species such as the Bumbleberry tree - one of which Papa is intending to cut down to make a very special table and chairs. By showing them how to recycle eggshells as plant fertilizer, Mama helps the cubs discover that even little cubs like them can help reduce waste. Not only do the cubs spread the word to their friends who come up with their own ways to recycle, they help Papa realize he should help the environment by planting new trees instead of cutting them down.
When a snooty new girl named Hilary moves into town, Sister's friends want to become just like her and join her "in crowd". Hilary has a snazzy new mountain bike, all the latest fashions, and the coolest music. Feeling a bit left out, Sister decides to give up jump roping and begins to want to join the crowd. However, she doesn't seem to fit in too well. Mama tells Sister that the best thing to do is to just be herself and do the things she likes to do. Then everyone will like her for who she is.
Brother and Freddy team up to try and create an innovative flying device for their fifth grade science project. Their hopes are dashed after a series of unsuccessful test flights and they decide to give up on the whole notion of being inventors. After having a talk with veteran inventor, Professor Actual Factual, the two cubs are encouraged to keep trying and ultimately they succeed in making a balloon-propelled aircraft that impresses the entire class.
Brother's tardiness causes inconvenience for many. Mama gives Brother a watch so he can be on time for important appointments, When Brother's watch goes off to go with Sister to the bookstore to see her favorite author, he puts off being on time. That's when Brother realizes that it's he who needs to decide whether he wants to be on time.
The Bears hold a family picnic for Mama's side of the family. Brother and Sister see members of the Bear family that they've never even met before. The cubs end up have fun in their own ways with their new relatives.
The Bears' next-door neighbors move in and they have trouble adjusting to their new neighbors, especially Papa. At first, Papa isn't used to the different neighbors apart from the ones they used to have. When Mama and the cubs show Papa how good different neighbors can be.
When Papa's complaints to the Mayor aren't addressed, he decides to take matters into his own hands and run for mayor. When Papa finds out just how hardd it actually is to be elected as mayor, he decides to drop out of the election and let Mayor Honeypot be the true mayor.
When Papa couldn't find a carving set to buy at the local hardware store, the clerk suggests that Papa should try looking for it at the one at the new mall. The Big Bear Mall is so huge, Mama goes over some rules with Papa and the cubs on how not to get separated. Papa doesn't pay attention to Mama and he loses his way while trying to find the hardware store. When Mama and the cubs finally find Papa, he finds the hardware store. All Papa had to do is get lost to find it. Papa promises not to get lost in such big places after that.
Brother and Sister donate a few of their old belongings to the elderly at the Bears' Retirement Home. When Brother accidentally donates his favorite book, he finds out that giving someone your time to read it is just as important as giving away your things.
Mama plans a trip to the movies so the family can spend some quality time together. But on their way to the theater, they get interupted by many things like running out of gas and getting rained out. When they finally arrive at the movie theater, all shows have been sold out. Despite the Bear family missing out on a movie, they have all been spending time together as a family on the ride to the theater. There is one kind of movie the family can watch and it can never get sold out: home movies!
Brother and Sister enter a pet show with Little Lady and Gran's parakeet. At first, Brother doesn't want to enter Gran's bird in the contest because she doesn't have talent. She can make different kinds of sound effects, but Brother doesn't think it's a special talent. When Gran shows Brother that he's looking at it all from a different point of view, it inspires Brother to show everybody at the pet show all the sounds Gran's bird can make that not many other birds can.
Rather than tidying his room, Brother spends his time constructing a birdhouse. His room is so messy, Brother and Sister stuff everything in the closet. But when Brother goes to get something from the closet, everything spills out and his birdhouse gets destroyed. That's when Brother and Sister learn an important lesson on getting organized.
The cubs plan a backyard circus. When everybody says that Brother's cycling technique is amazing, Sister feels hurt because she is the one who's going to do that act and she thinks they like Brother's act more than hers. Brother feels as hurt as Sister when Lenny and his dog steal his act with Little Lady. When Sister finds out how Brother feels about losing his dog act, just like when she lost her cycle act, she gives Brother a hug to make up for it all. The cubs all work out their acts for the Bear Country circus.
Too Tall, Brother, Freddy and Kenny all participate in a go-cart race. Brother is in charge of building the go-cart, Too Tall is in charge of providing parts for the go-cart, and Freddy is in charge of drawing the plans for the go-cart. As for Kenny, who helps the cubs along the way, he ends up getting the honor of driving the go-cart in the race.
Papa is so busy in his workshop, he has no time to practice for the upcoming Spring-Fling Dance Jamboree with Mama as his partner. Brother decides to volunteer, despite the fact that he can't dance. But with Mama showing Brother a little about "'magining", Brother finds that dancing can be fun.
A lack of manners at school frustrates Sister, whilst Brother also forgets his manners. With Mama's and Papa's advice about using the magic words, please and thank you, Sister and Brother mend their troubles by saying those words to everyone at school the next day, especially their school custodian.
At cub camp, Two Tall and his gang have trouble keeping up with the various activities, but they intentionally refuse to ask for help, especially Too Tall. When Brother offers to help Too Tall with his canoeing practice for a race, Too Tall accepts Brother's assistance.
When Too Tall and his gang decide to build a tree fort in the tree home to a rare bird, the cubs try to convince them otherwise. When the cubs come up with a compromise, Too Tall and his gang end up making an even better tree fort than they even dreamed of.
Papa has troubles with an old tree stump whilst Brother and Sister have trouble making a scarecrow to frighten the birds away from the garden. Mama shows them that there's always a good side to every problem.
When Brother and Sister invite a lot of friends over, they have trouble deciding what to make for lunch. Each friend has some foods they like and dislike, and it's hard for Brother and Sister to keep track. Papa, however, has a way that everybody can be happy and have what they want. He can make them pizza!
Brother, Cousin Fred and Too Tall enlist the help of Betsy Broom to help them win their upcoming football game. Betsy, however, also has activities she needs to tend to. With help from the cubs, Betsy helps them in return with their football plays.
Sister gets frustrated and impatient when both her fur and her seed aren't growing quickly. Mama and Gramps tell Sister that things can't be rushed and they need patience to help grow.
The Bears' are invited to the Bruins' cottage to do some fishing. Papa gets so excited he ignores Sister's and Brother's suggestions of preparation. Everytime a cub needs something they forget to take with them for fishing, Papa has to go up and down the steps to get it for them. The cubs all show Papa how important it is to plan ahead and list everything they might need to take.
Brother gets his own key to the treehouse which causes him to think strongly about growing up. When he helps Papa with some grown-up work, Sister and the other cubs think he has no more time to play with them. Papa shows Brother that just like grown-ups, cubs have important jobs too.