Caillou wants to play, but everybody's too busy to play with him. Caillou's Mom has to do the taxes, Caillou's Dad is repairing the washing machine, and Caillou's grandma is tucking Rosie in for her nap. Even Gilbert doesn't seem to want to play. Caillou then goes back into his room and plays with his plush toys.
It's Caillou's first day at daycare, and he's whining because he doesn't want to go - He wants to be at Grandma's instead. We meet with Mrs. Martin, Caillou's teacher. Caillou's mom then leaves. Mrs. Martin gives Caillou some juice. Caillou then tries to befriend Leo, but Leo was rude to him. Enters Clementine. She introduces herself to Caillou, and explains to Caillou that Leo "doesn't like to share". She shows Caillou what she has been doing: cutouts. She then asks Caillou why does he prefers his grandparents' place. He tells her that he likes painting. She explains to him that they can do that at daycare, too. She brings out some paints, brushes and paper. Caillou paints a robin as Clementine cuts out some paper worms. Leo walks by, and notices Caillou's painting of a robin. He wants Caillou to teach him how to paint. Caillou aggrees, on the condition that Leo teach Clementine and him how to build castles with blocks. And so, we see Leo paint a (distorted) robin while Caillou and Clementine build a castle out of blocks. Caillou's parents then comes to pick him up. Show comes to a close as Caillou says that he wants to come back tomorrow.
Caillou's grandpa is over at Caillou's place. They're playing about when Caillou's grandpa reminices about the time he went camping with Caillou's dad a long time ago. Caillou wants to go camping, too. So they do. They set up a tent and go nature hiking around the garden. At night, they have marshmallows and look at the stars. Then it was time to sleep. But it was too noisy. Grandpa has a solution, though. The next thing we know, we see Caillou's mom calling them up for breakfast. And the tent's in the living room. Turns out that the night noises frightened Caillou. So they moved everything indoors.
Caillou is drumming and singing badly. Mom tells Caillou to quiet down so Rosie can take a nap, but he doesn't want to at first. Eventually he stops and heads off to the kitchen to get some cookies. They're hard to reach though, so he tries to use a stool and ends up spilling the cookies as well as a jar of honey. He tries to make honey cookies, but ends up making a mess. Mom comes in and decides that rather than get upset about it, she'll just have Caillou help her clean up. He does and then he and Mom make cookies together. Sometime at the park, apparently later that day, Caillou and Mom share the cookies with Dad and Rosie. Then Caillou runs off and starts covering himself with mud. Dad asks him what he's making and he answers "a big mess."
Caillou's Mom brings up laundry to his room and he needs a pair of socks. He finds one, but not the other. He goes down to the basement to look in the washing machine. He's too short to reach the washing machine, so he goes up looking for a chair, but the doorknob breaks off the door. Daddy is around and he opens the door. They go down to look for the sock together, but it's not there. Mom closes the door again and they get stuck downstairs once again. They call Mom and she opens the door. Dad goes to fix the door and Mom shows Caillou the laundry basket. His sock was in there the whole time.
Caillou's sleeping over at Leo's place. He nearly forgot Teddy, but then remembers just in the nick of time. At Leo's place, Caillou has lots of fun, but got homesick when dinnertime arrives. By bedtime, Caillou wants to go home, but after a phone call to Mommy, Caillou decides to sleep over after all. The end.
Caillou's in the garden with mommy when Sarah comes over and shows Caillou her magnifying glass. Caillou and Sarah plays jungle explorer, pretending that a caterpillar is a jungle monster and Gilbert is a ferocious lion. Caillou and Sarah then hears a really loud noise. Caillou thinks that it's jungle drums, but Sarah thinks that it's just thunder. Caillou then go relates his story to mommy, who tells him that the noise is sending them a message: go indoors lest you want to get wet. The end.
Leo tags along with Caillou and his family on a picnic. They play Knights and Dragons, have the picnic lunch, and play some more. Suddenly, thunder can be heard. Caillou and Leo pretends that it's a dragon's roar. Rosie's beginning to fret because of thunder, but Caillou and Leo pledges to protect Rosie. It then starts to rain, so they quicklly pack up and run for the nearest cave. They then proceed to keep Rosie occupied so that she ignores the thunder. The rain finally stops, and they all head home. The end.
Caillou is afraid of Mr. Hinkle, and when Mr. Hinkle waved to Caillou, Caillou panicked and ran. That made Mr. Hinkle really sad, so he goes over and apologizes. Caillou's Mom couldn't get Caillou to go downstairs, so they engage Caillou in a game of "Hide and Seek". In the end, Caillou is no longer afraid of Mr. Hinkle. As a matter of fact, Caillou decides that he likes Mr. Hinkle after all.
Caillou dreams that he's a lion tamer and Gilbert is a lion. He then wakes up. He remembers that he is to go to the circus today. He quickly gets dressed. Caillou's dad then comes by the toilet and asks him why he's up so early. Caillou explains that he can't wait to go to the circus. Caillou's dad corrects him - the circus is tomorrow, not today. Naturally, Caillou throws a tantrum. Later, during breakfast, Caillou's dad accidentally grabs hold of burnt toast and starts juggling them. It's then that Caillou gets the idea of playing circus. So they do. Then, Caillou's mom comes downstairs. Caillou's dad asks her if she wants to play the lady that rides the horse. She replies that she'd rather go back to bed. The end.
It's bedtime, but there's a scratchy noise coming from somewhere in the room. Caillou thinks it's a scratchy monster. Caillou's parents thinks that it's the tree branch brushing against the window. But when the scratching noise continues, Caillou gets all delerious in the dark and mistakes his parents for a two-headed monster. The ""scratchy monster"" then appears. It was Gilbert all along, stuck in a paper bag under Caillou's bed! Caillou then learns to use Teddy as an ear-muff. The end.
Caillou complains to his grandma that he has no friends. Caillou's grandma then asks him about Leo and Clementine. Caillou admits that Leo and Clmentine are his friends. Then she reminds Caillou that Rosie may be his sister, but she's his friend, too. And so is Gilbert and Mr. Hinkle. And lastly, so is his Mother and Father and even her - Grandma. The end.
Caillou wants to make a snowman, but Caillou's mom wants to take him shopping for ingredients to make a special surprise cake. At the store, Caillou sees a box of cookies, but his mom asks him to put them back. So he does, and they head to the checkout line. However, while waiting at the counter, Caillou suddenly thought of the cookies, and tries to find his way back to the cookies, only to get lost. He breaks down and cries, and it isn't long before his mom finds him. Back home, it turns out that the cake is a snowman cake. The end.
Caillou's parents are going out, and Grandma's coming over to babysit. Later, it's naptime, and he dozes off. Until Glibert comes and wakes him up. Then he has trouble going back to sleep because it's too bright. Grandma comes up with an idea - a cardboard cutout of the night sky, and Caillou eventually falls asleep.
Caillou and Rosie are playing in the leaves. His parents join in. Soon, Caillou's mom has to go in and make supper. But Caillou decides that he wants to help his dad rake the leaves. While doing so, he imagined that the leaf piles were big houses. Soon, it's getting dark, and the leaves are raked. They head indoors, and Caillou that he has a leaf on his head. The end.
Caillou's at Grandma's and he's in a bad mood. He doesn't feel there's anything to do. Caillou insists anyway that he's not grumpy and not hungry either and doesn't want apple pie. Caillou decides to fingerpaint using Grandma's paints. Then, Grandma convinces him to have some pie, but only after getting cleaned up. Then his Mom comes to pick him up. Grandma tells him he can come back if he's ever grumpy again.
Caillou's family is at a pool, but Caillou is scared of the big pool and wants to stay in the baby pool where Rosie is. Caillou's dad decides to teach Caillou how to swim. Caillou seems to be making progress, but he is scared again. His dad helps him realize that he can stand in the water, and Caillou's feeling confident again. Caillou is soon going to be an aweesome swimmer.
Caillou's visiting the park with is grandpa when he comes across new. The boy introduces himself as Jim. Jim's mom then comes about and heads off with Caillou's grandpa. Jim, however, was the brash kind. He just simply grabs whatever he wants without asking. Caillou is intimidated and decides that he doesn't like Jim. Jim's mom then comes around again and have a talk with Jim. So, finally Jim realises his mistakes and apologizes to Caillou. Apology accepted, and they're both friends now. The end.
Caillou's Mom and Rosie are going out for the day. This means he and his Dad can finally work on a surprise for Caillou's mom: A bookshelf. They then accidentally get paint all over themselves when they realized that they haven't any paint to go on top of the undercoat. So, they go out and get some. Then they grabbed a hotdog. When Caillou's mom returns, she's pleasantly surprised by the shelf, and the book Caillou made for her that's on it. The end.
Caillou and his daddy arrive at that park and Caillou goes to the playground and pretends that he is on train. Then, Clementine shows up and wants to go down the slide. Caillou slides down one of the small tubes, but Clementine wanted him to go down the big slide. Caillou doesn't want to, so he convinces Clementine to continue playing train with him. Soon, Clementine wants him to go down the slide. Caillou tries not to be afraid, but once he gets to the top he is very scared and tells his daddy to come up with him. Daddy convinces Caillou to slide and they go down together. Clementine isn't impressed that Caillou was so scared. So Caillou goes down the slide alone. It is then time to go home, but Caillou asks his daddy if he can do it on more time. Caillou ends up having so much time that he ends up sliding many times before he and Clementine are finally ready to go.
Caillou's grandma is watching Rover again. Caillou takes Rover out for a walk. Rover is a very obedient dog. When they reached the park, Caillou plays with Rover a bit. Caillou then decides that he wants a pet dog. But they already have Gilbert. SO, Caillou attaches a leash to his plush dog and pretends to walk it. The end.