Little Briar and Bramble run off to Pine Tree Mountains, followed by young Vick. The young boy is surprised to find many forest animals there. Miss Olivia tells him not to be afraid and encourages him to make new friends.
Bramble is reluctant to go to kindergarten. Even once he gets there, he is unhappy. Eventually Tiki comes up with a cunning plan to make Bramble forget all about his sadness.
The little ones find themselves in a cave filled with fireflies. Sadly, one firefly doesn't glow so they try to help it, but nothing seems to work. Coach Mack shares some interesting information with everyone.
Coach Mack and the kids are off on a camping trip. Everyone is ready to put up their tents, pick fruit and enjoy a picnic. Along the way, they learn some new skills.
Bramble relies on his brother Briar to do a lot for him. Briar helps him in class, walks him to school, shares his food. However, a tricky math problem makes Bramble realize that there are some things we need to do for ourselves.
In class, the cubs learn how to grown watermelons. Despite missing the class, Vick reckons it's easy and refuses any help when growing his own watermelons.
Briar and Bramble invite Hoo Hoo to their home. Trying to be good hosts, they go overboard giving Hoo Hoo their warmest welcome. Mama Bear advises that the pair learn to walk in others' shoes to realize what their friend actually needs.
when Bramble finds himself too short to reach the blackboard, he does everything he can think of to grow taller. However, Tiki points out that his method for measuring himself may not be the best.
During a spring clean, a pile of old toys are discovered. Vick suggests they share them among the kids, but nobody wants them. Old Billy helps the kids donate them to another kindergarten.
The cubs accidentally break a trophy they won in a sports competition. They don't want Miss Olivia to be mad at them so they make up a story about some birds attacking the trophy.
The kids at Pine Tree Mountain Kindergarten welcome a new classmate named Violet. They try to include her and make her feel welcome, but she doesn't seem to want to play with them.
Bramble adopts a caterpillar, curious to see it change into a butterfly. He worries that the caterpillar may need his help during the metamorphosis process, but Miss Olivia convinces him to just give it time.
The cubs are discussing what they want to be when they grow up. Vick wants to be an inventor. To prove his desire, he tries to make a few cool inventions. However, they don't work and Vick becomes disheartened.
The kids decide to pick some flowers and decorate the classroom. Unfortunately, they end up making a real mess and damaging lots of plants. Miss Olivia teaches them an important lesson about looking after flowers.
Another new classmate arrives in Pine Tree Mountain. This time it's Ernie Jo, who has really big ears. A rumor starts that Ernie Jo's big ears are infectious and so the cubs try avoid the newcomer.
When Briar receives praise from Miss Olivia for building a tower from blocks, Tiki becomes jealous. He thinks his block tower was better. During nap time, Tiki has a strange dream.
Violet simply hates rainy days. She cannot understand why everyone else is having fun as usual. She tries practicing her flute, but raindrops cause it to become out of tune. Violet gets even more upset about the rain.
Pine Tree Kindergarten is offering a lot of new classes and Bramble wants to attend all of them. However, he doesn't consider how much time and effort is needed to succeed in so many classes.
Briar has toothache. Vick tells him that bugs are eating his teeth which makes him very anxious. He tries really hard to get rid of the bugs but eventually he has to visit Nurse Beakman.
Miss Olivia is unavailable for class today, so Old Billy becomes a substitute teacher. At first, the cubs are no interested in Old Billy's lesson, but in the end he manages to win them over.
Luna Loo loves the moon stone inside Violet's treasure chest. So she hides the chest making Violet very upset. However, Ms. Lady Jane witnesses the whole thing.
Today is Little Teachers Day at Pine Tree Kindergarten but Vick has not prepared. His lack of planning causes him to make mistakes and feel let down by himself.
After misbehaving in class and refusing to apologize, Briar is worried about Miss Olivia's visit to his house. He doesn't want his mom to find out about his bad behavior so tries everything he can think of to prevent the visit.
Today's class is about planting beans. Coach Mack reminds the cubs that their hard work will pay off, but Bramble gets distracted by a butterfly and misinterprets the message.
Old Billy correctly forecasts the weather so Tiki asks to be taught how to do so himself. Unfortunately, Tiki's predictions aren't quite right. Maybe something went wrong?
Herby hears that there are lots of ripe, sweet apples just the other side of the mountain. On his way back home, he bumps into his friends. After sharing his apples with them, he has none left for himself.
Violet teaches the others how to skateboard. However, Bramble can't quite get the hang of it. Violet tells Bramble some magic words to help him succeed.
Bramble is sick with a cold so can't go today's picnic. Vick and Briar give him a fish to keep him company. Once he recovers, Bramble is excited to play with his friends again. However, he returns home to find that his fish is gone.
The kids at Pine Tree Mountain are upset about their supposed bad luck. Vick tells them the story of the mysterious Forest Guard who helps people in the forest, but only if they do good deeds first.
Violet brings a conch to class. When the cubs put it close to their ears, they hear a beautiful sound. Vick realizes it's an echo and explains to his friends how echoes work.
Tiki loves to prank his friends. When Vick joins forces with him, the pair hatch an evil plan. It seems that this time they have taken their pranks too far.
After only taking a few bites from his apple, Vick decides to save it in a drawer for later. When he remembers about it a few days later, the apple is rotten and moldy. Vick and Bramble want to know what happened to the apple.
Tiki loses one of his baby teeth and feels embarrassed. He starts behaving oddly. When his friends find out the reason why, they do their best to cheer him up.
Today the cubs are thinking about their futures. However, Ernie Jo doesn't know what he wants to do when he grows up. Eventually his friends help him discover what could be his calling in life.
The cubs all work together to prepare a salad. All except Tiki, that is. But having not helped prepare the food, he still expects to enjoy eating the food. His friends have other ideas.
The leaves on the trees are changing color, but Briar and Bramble don't want them to fall of the tree. With the help of their friends, they try various methods to save the tree.
Miss Olivia asks the cubs to draw a picture and tell the class the story behind it. When Tiki copies Babu's artwork, he is unable to come up with a good story to tell.