Jonas, a friend of Dad's and a real cowboy, has invited the family to visit his ranch.
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Caillou accompanies Mom to the grocery store and brings along some money from his piggybank. When Caillou, Grandpa and Daddy go on a canoe trip, Caillou gets to see some wild animals in their natural habitat. On an autumn day, Caillou and his Mommy take a walk and pass by a construction site. When Dad's burning toasts trigger the fire alarm, he decides it is the perfect opportunity to practice a fire drill. Caillou and his Mummy are finishing preparing a picnic lunch.
When Mum, Rosie and Caillou go to the zoo, Caillou can't wait to see the elephants. Grandma takes Caillou on a special visit to a sheep farm. Caillou and Dad go over to Mr. Hinkle's house to help him build a dog house. While Caillou and his family are on a picnic at the park, his beach ball accidentally rolls into a pond. When Mum takes Caillou to Clementine's to see her new pet, she won't tell Caillou what kind of animal it is.
When a white rabbit eats a bunch of carrots set aside for a picnic, Caillou and Rosie go looking for him. Caillou and his family are leaving for a picnic in the country but the ride feels very long for Caillou, especially since he cannot play with his toy airplane because he might wake Rosie. When Caillou visits Clementine, he is impressed to see Billy practicing on a Tuba. On a winter evening, a strange sound grabs Caillou's attention.
Caillou gets a special invitation to go to Andre's gym class. Caillou and Leo are playing with their rocket ships in the park. On a winter day, Dad and Caillou go over to Grandpa's with their skates. When Caillou and Rosie stay at Grandma and Grandpa's house, Grandpa uses pop bottles and a rubber ball to create a kid's bowling alley in the backyard. Caillou accidentally spills the rest of the milk before Rosie could get her cereal.
It is a rainy day and Caillou is disappointed because he will not be able to go play at the park with Grandma. It's Valentine's day and Caillou is invited to a Valentine's party at his best friend Leo's house. When Dad's baseball team, the Tigers, are playing a game at the park, Caillou, Rosie and Mom, go to cheer him on. Caillou and his family are heading to the tobogganing hill!
Leo is spending the night at Caillou's. Caillou is excited when Miss Martin takes him and his friends to the park for some special activities. Caillou discovers how maple sap is collected from maple trees and gets to help to collect some. The twins, Jason and Jeffrey, have come to play with Caillou in the snow. When Caillou, Rosie and Mum head to the big park, Caillou sees André and they decide to build a snow fort.
Grandma has given Caillou a special spaceship plate, which he loves! It's raining outside but there is no stopping Caillou! After finding a photograph of a four-year-old Dad with a model train set, Caillou and Dad decide to look for it in Grandpa's basement. When Caillou spots a dog house outside he gets the idea that Gilbert might like a house of his own. Caillou, Rosie and Mum are having fun at the park when the ice-cream man comes around.
Caillou just loves his Superbear storybook and decides to make up a story on his own and plays it out with Rosie. Caillou learns to deal with a change in plans, when Daddy has to use the car and Mummy and Caillou have to take the subway. Caillou is playing a board game with Mum and he gets a little upset when he discovers that her last die throw is going to make her win. When Caillou gets an eyeful of Leo's new bicycle, he wishes his bike looked special too.
When the park is closed for the day, Caillou's friends come over to his house to play. When Mum drives Sarah to her skating lesson, Caillou decides he wants to take skating lessons too! When Mum and Dad are getting ready to go out to a restaurant, Caillou doesn't understand why he can't go too! When Caillou accidentally breaks one of his toys because his room is a mess, Mum suggests a way to make cleaning up fun. When Caillou dresses himself, he learns it's okay to change from your favourite shorts when you find out it's cold outside.
When an invitation for Clementine's party accidentally ends up at Sarah's, Caillou learns the differences between the addresses of the two homes. When Leo forgets his brand new toy dinosaur in the park, Daddy and Caillou go looking for it. When Clementine tells Caillou how much she likes her older brother, Billy, to teach her things, Caillou sets out to teach something to Rosie. When Caillou's dawdling causes he, Mom and Rosie to be late going to the park, they end up missing Leo. When the washing machine needs fixing, Caillou ends up helping Bob the repairman.