It is early winter in the country and George wants to play outside. But the problem is he has toys for summer and snow but no toys for just plain cold. He decides he will have fun by playing with Bill's bunnies but Bill is taking them to his grandmother's house for the entire winter. Bill wants him to leave out nuts and seeds for Jumpy Squirrel all winter and George wants to find a way to have fun in the winter cold. Later, after he sees how the water in his pool is frozen, he finds a way to have fun outdoors AND give Jumpy the food he needs.

George is trying to get up his game and practice soccer, but Steve & Betsy's Aunt Margret says he must dogsit their dog Charkie. Charkie is very wild and playful and does anything she can to run away from the back alley where George is trying to practice. It seems like every time George has an exit covered, Charkie find another way out. George has to find a way to get her to calm down and sit.

George and the Man go bird-watching at the park.

George has found himself a new friend in the city, Compass. One of the Doorman's homing pigeons which he keeps on the roof of the apartment building. But the only thing is, Compass has a bad sense of direction. So when the Man says George is not allowed to let pigeons inside the apartment, George decides to build Compass a new home on the balcony outside their apartment, eventually deciding on a tree. But soon George finds out building a tree is not as easy as it seems. Where do trees in nature come from if people don't make them?

George visits the dentist.

Professor Wiseman is taking George to his first dog show which, to his disappointment, is not a show performed entirely by dogs. But when he gets home, The Man with the Yellow Hat wants to hear about all the dogs but George can only remember three. So he goes back to try to take note of them all and eventually brings them all home where he must find a way to organize them to count them easily.

George comes across his friends Steve and Betsy playing basketball in the city. When George tries to play, he finds out he is not very good and winds up losing the ball when it accidentally lands on a moving pickup truck. They then decide to play miniature golf instead. After Steve tells him that when playing basketball, the winner is the person that has made the most baskets has the highest score, George figures it is the same way for golf. Then Betsy tells him that in golf, the lowest score wins. Since they find the park mini golf course too hard, they decide to build one of their own.

The Man in the yellow hat is competing in the country town bowling tournament at Bowlmore Lanes but it seems like George does not have any luck getting the ball to hit the pins because it keeps falling into the gutter. When he sees The Man polishing his bowling shoes because they make it extra lucky, George decides to polish his bowling ball too. After George polishes the ball he decides to give it a test roll. However, the yard is bumpy and the driveway is a hill so he just cannot get the ball to roll straight. That is until he keeps the ball so long that The Man forgets it and George sees the road from the country house to the Bowling Alley is like a big bowling lane with gutters.

The Man with the Yellow Hat takes George to his checkup. George has never seen a doctor's office or a doctor before and becomes curious. After the doctor has to take a break, George puts on his coat and uses his equipment to try to track down a strange "bloopy" sound he had been hearing and, along the way, has to help several patients such as a woman with allergies a man with a broken arm and a woman with hiccups in the way only a monkey can.

George is pretty mad at Hundley who will simply not let him play in the lobby and wishes Hundley could be more like him. One day though, he notices that Hundley is barking loudly and acting bouncy and playful, much to his wish! He then notices that Hundley seems to go back and forth between acting bouncy and playful, and acting like his normal self. Realizing that something is not normal about Hundley's split personality, he tries to figure out what is going on.

George uses shadow puppets to help Allie.

George wakes up on a windy day in the country. His friend Bill introduces him to a kite, which George wants to fly. However, Bill must go home and George cannot play with the kite until he returns. His curiosity gets the best of him and he soon finds himself flying around the countryside, even taking his friend Jumpy Squirrel with him. This is the pilot episode for the series.

The Man with the Yellow Hat has a predicament. He has to write a tribute speech for Professor Wiseman. Also, the country house cupboards are too small to hold all of their food. Then when Bill tells him how squirrels store food in the ground after seeing Jumpy Squirrel do it, George decides to do the same thing to their food. When the Man finds out, he tells George that squirrels bury nuts, seeds and things that grow. So George decides to plant and grow various objects around the house including the Man's speech which he wants to grow the rest of.

George and The Man with the Yellow Hat go to the country to feed ducks but have to put their plans on hold when the Renkins' chicks are missing and they must find them. George, however finds a raft on the edge of the river and soon, along with Jumpy Squirrel, finds himself-literally-going up the creek without a paddle. They eventually find a way to stop but they must now find their way back home to the Renkins' farm.

The Renkins' are having a problem with their grape yard. A group of gophers have made their home in the ground under the garden and are stealing the grapes. Upset with the problem, Mr. Renkins calls Calhoun the Gopher-getter, an exterminator, to come and catch the gophers. George does not like the idea of somebody catching the innocent gophers, even if he does plan to release them again. So he decides to build a connecting tunnel between his house and the Renkins' garden so the gophers can escape.

George is outside watering the garden when he gets muddy. He tries to take a bath but there's no water. Not even in the sink. Mr. Quint explains that they have a broken pump. And then he explains how to get the water, with a well and a pump. The pump they have is old. Then The Man explains that an electric pump sends it through a pipe to the house. And they go back to the city since it'll take days to get a new pump. When the go to the apartment, they don't see an orange flier. It says the plumber must shut off the water now. This means there's no water here, too. So George tries to get more water with a pipe.

George's friend Professor Wiseman has a pretty interesting habit-building and fixing clocks. She has just finished work on a very interesting clock where a band comes out and plays every hour. But when Compass comes flying in and George tries to show him the clock he accidentally breaks it and then winds up taking it completely apart when he tries to fix it. George goes to the library to try to find out how to fix it but not from a book. The library has a big clock tower on top that the whole city depends upon. But when the clock's chime scares George he winds up breaking the big clock as well.

George is on a city-wide smelling spree when he comes across Chef Pisghetti's kitchen. Chef Pisghetti is cooking a meal for a famous restaurant critic. Then George comes across some pasta the chef was cooking and had placed in a pot. He notices that it had been crisp but is now all floppy. George then decides that kitchens are magic and finds other things to place in the "floppification pot".

George has gone to his favorite country place, Lake Wanasinklake, where he finds Bill fishing in the lagoon. Bill has caught not fish, but tadpoles and he asks George to look after them as they grow up because "they do some amazing things". But when George figures they are growing tired of the same, small fishbowl, he decides to release them into the lagoon. Later he tries to do anything to get them back but only catches a small green creature which is not one of his tadpoles. Or is it?...

George has to stay with Hundley in the lobby as the apartment gets cleaned but Hundley does not want George to eat his messy snack in the lobby. After George and Hundley get locked out in the alley behind the apartment building, Hundley runs off trying to find a better way in. George follows him and they eventually meet in a place very far away from home. They decide that, since it is dark out and they can not see their way home, they can hear their way home instead.

The Man with the Yellow Hat is about to become the world's first untrained person to fly into space so he can deliver food along with several experimental capsules to the International Space Station. But the spaceship designed by Professor Wiseman's assistants Professor Anthony Pizza and Dr. Alvin Einstein is only designed for someone with four hands. So, George winds up being the world's first monkey in space. George is told that he must activate the system that releases the goods for the station at a certain point and that his spaceship is in an orbit around the earth so he will eventually get back around to the station.

George is having the time of his life playing with his toy boat in a large pond. After one day of playing, though he comes back the next to see his pond almost empty. George finds out that the water is being held back by a dam that was built by a family of beavers, and they will not let him play in their pond. So George gets the idea to build a dam of his own to make a new pond. He later finds out that water is just as important a part of a beaver's home as the dam.

The Man in the yellow hat is trying to get ready for his photo on his new licence but when George tries to help, the ensuing chaos ruins the Man's hat! The hat is cleaned and restored like new and the Man puts it on the kitchen counter right next to an identical looking box of trash. In a rush, George accidentally throws out the box with the hat and must go on a city-wide spree to find it. Unfortunately it seems like every trash can and dumpster in the city George finds has already been emptied by the garbage truck. George finds some disposed items at Pisghetti's restaurant but Chef Pisghetti tells him that it is not trash, it is recycling. He tells George to go look for the hat in the landfill.

The Man With the Yellow Hat is about to get a big job! He is going to go up into space to fix the Einstein-Pizza Space Telescope, which is broken and pointed right at Pizza's kitchen window. Dr. Einstein and Professor Pizza explain that the spaceship has a self-locking air lock but they accidentally forgot to make a way to open it from outside. George has to tag along to push the button that would let him in but is forced to go outside and do the job when the Man's tether breaks. Worse off, George is told he has only 2 minutes of air to complete the job.

George is at Betsy's birthday party and sees that they have something he has never seen before, a piñata! After George is told how to play, he goes on a free-swinging spree and winds up breaking everything in the backyard BUT the piñata! Aunt Margret tells George to stay outside and play with Charkie and asks him to put his blindfold on and follow her around the backyard with his other senses. Charkie soon escapes the backyard and a blind George begins to follow her around the city in a way other than seeing her.