Gilbert has gone missing and Caillou is very concerned. After a day in the park and a visit to an ice cream parlour with Jeffrey and Jason, Caillou realizes that he has misplaced his new toy car. Caillou learns all about the jungle at playschool, and decides it would be an exciting place for a game of hide and seek.
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When Clementine shows up with a swimming ribbon on her chest, Caillou really wants to have one too. When a new, longer set of monkey bars is installed at the park, Caillou is disappointed that he can't climb as far as Leo. After imagining himself riding in a real grownup bike race Caillou decides he's ready to try riding without his training wheels.
The children all pitch in to help clean up the playground and when Caillou and his friends, Leo and Clementine, finish their cleanup duties they decide to build a road through the sandlot. When Daddy and Grandpa help a charity build a new home for a needy family, Caillou comes along to help hand out sandwiches. Caillou's never been in an apartment building before and finds it to be quite an adventure.
Rosie is teething and just can't seem to fall asleep, so big brother Caillou decides to help. The Fire chief visits Caillou's playschool to teach the children about fire drills. Leo and Caillou have a grand adventure pretending they are tow truck drivers and crane operators rescuing toy cars from the pillows of the sofa.
The playschool is going swimming, and it's Caillou's very first time on a water slide, but he's a little nervous and doesn't want to slide down it. Mummy and Daddy are going out to a party and Caillou is excited to hear that Grandpa is coming to babysit. Caillou decides to teach his little sister about all the different kinds of insects in their backyard.
Caillou eagerly awaits the first snowfall of winter, and imagines himself building the biggest snowman in the world. Caillou wants to play hockey with Billy and the other big kids, but he finds he just can't keep up with them. Mummy can't find Caillou's toboggan for the playschool tobogganing trip and Caillou is certain he'll miss out on all the fun.
Clementine's big brother Billy has a new drum set and is having lots of fun playing as loud as he can. Caillou and his friends are very excited when a real marching band goes by the playschool and they decide they want to be in a marching band too. The playschool is having a talent show and Caillou wants to sing a song, but Clementine beats him to the punch, picking the exact song he wanted to sing.
Caillou has to decide on a nice surprise to bring to playschool for Show and Tell. Grandma shows Caillou a simple magic trick, which makes him decide to be a magician. Caillou wants to play castles and dragons, even though Gilbert isn't very keen on playing the dragon.
Since it's so hot out, Daddy treats them to ice cream and Caillou imagines he's down at the cool cool south pole playing with the penguins!There's a new girl named Lee Wun in playschool, but she's so shy she won't talk to anybody.The whole family is on the way to the beach but accidentally end up on a trail through a swamp.
Caillou is playing with the fridge magnets and learns lots of things about them. The whole family goes on a trip to the natural history museum to look at the dinosaurs. Caillou is really enjoying himself looking at the skeletons and learning about the different kinds of dinosaurs. Caillou wants to play with both his friends Clementine and Xavier in the playschool playground. Unfortunately Clementine wants to play bears and Xavier wants to play astronauts, and a little argument ensues.
Caillou is excited about showing Rosie the ropes when they visit the library. Returning home from the library Caillou is very eager to sit down and enjoy his pirate book. Unfortunately it's a very busy day and he's having trouble finding a quiet place to look at his book. It's a rainy day at playschool and the children can't go outside. Caillou makes up a funny story about a superhero who makes the rain stop - it's Super Caillou!
At playschool Caillou decides to make her a present to cheer his Mum up when she is having a bad day. Jeffrey and Jason are coming over for dinner - it's a make-your-own pizza party! Caillou feels he is an expert at this and starts to show them how to do it. Caillou's got a brand new painting shirt and decides to paint something for Grandma, but he has a little trouble deciding what to paint.
Grandpa's got a surprise for Caillou on their trip to the park - it's a remote control sailboat! After expressing an interest in loud machines, Daddy takes Caillou to the airport to see the airplanes. Daddy and Mummy's friend Jonas is getting married. The kids are very excited about the ceremony - Caillou is the ringbearer and Rosie is the flowergirl.
Caillou's crayons are all worn down or broken, so Mummy suggests a trip to the store for some new ones. Caillou's playschool is on a special field trip to an apple orchard. Halloween is coming and it's time to pick out a costume to wear. Soon Rosie has three costumes she wants to wear, but Caillou still hasn't decided on what he wants to be.
When birds keep eating the seeds in Mummy and Caillou's newly planted garden, they come up with the idea of making a scarecrow. One fine day the family is going on a car trip. Daddy says he doesn't know where they're going, they'll just see what they can find. There's a special visitor at Caillou's playschool - a boy named Alan who has Down's Syndrome.
When Caillou accidentally breaks Mummy's favourite cup, Grandma suggests they make her a new one. When Caillou finds out that Miss Martin's birthday is coming up, he wants to do something very special for her. Sarah is playing at Caillou's house when a sudden rainstorm causes a power outage.
While pretending to be a jet pilot Caillou falls down and scrapes his knees. Even though it hurts, he likes the extra attention from Mummy and Rosie. When the traffic lights near school stop working a policeman comes to direct traffic. Caillou loves watching him and learns from Miss Martin about lots of different ways that police officers help people. Grandpa takes Caillou to the park one find day to meet his friend.
Caillou goes out caroling for the very first time with Mummy, Daddy, Rosie, Grandpa and Grandma. It's a very special day at playschool as they celebrate the many ways of celebrating the holiday season. It's finally Christmas Eve and Caillou just can't wait for nighttime.
It's Valentine's Day and Daddy surprises Mummy with a bouquet of roses. Caillou is very sad when his snowman melts away in the warm spring sunshine. He doesn't want winter to end. After Daddy plays a trick on Mummy, Caillou wants to get into the spirit of April Fool's Day.
Caillou is helping Grandma water her flowers and fill the birdbath. Caillou and his friends Jason and Jeffrey make finger puppets at playschool and decide to put on a puppet show for the rest of the class the next day. In the park Caillou starts a new hobby - collecting rocks!