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 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?

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 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 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.

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.

On their way to the museum, the Man with the Yellow Hat and George discover that Gnocchi the cat has been accused of scratching the booths in Chef Pisghetti's restaurant. George isn't sure that it was Gnocchi and sets out to solve the mystery. George uses reasoning to find out that the scratches he had seen on the booths were not like scratches he had seen Gnocchi make on the door and he uses pieces of food to measure the length and depth of the scratches.

One day George is walking the street of his apartment building trying to find something to do when he notices a woman leaving numbered boxes outside every building. He decides to be a helpful monkey and return them to her until his friends Steve & Betsy tell him that she is a postal worker and that leaving boxes for people is her job. So they go on a race to see who can finish returning packages first. Winner plays Steve's video game. Steve has a plan to simply run fast but George and Betsy come up with a plan to sort all of the packages by the number of the buildings they go to.

On a sunny city Saturday, George and the Man decide that it is a good day for donuts and eggs. The Man tells George to write down the number of eggs they have in the refrigerator but George does not write anything because they had none. The Man then realizes that after teaching George everything for so long he forgot to teach him about nothing! He says that zero alone means nothing but when added to smaller numbers makes them bigger. The Man then sends George off to get the donuts with a paper that has an order of 1 Dozen Donuts. But George does not know about a dozen and changes the order to 100 dozen donuts. But after seeing just how many donuts 100 dozen make he tries to do anything to get away with only 1 dozen.

George and The Man have just brought home a new rug. The Man thinks it is so perfect he would like to take a picture of it. But when he runs out to get some camera batteries George decides to have a drink of grape juice and spills it on the rug! George knows how to clean it up, though—a lot of soap and water. But he uses so much he fills up the whole house with suds and water. Luckily he knows about the time his friends The Renkins' basement got flooded and they cleaned it out with a pump. George finds the pump at their house but has no easy way to get it back home.

Continuing from the previous part, George wants to continue helping Chef Pisghetti in his kitchen but the chef has no work for him. But the chef has a friend named Mr. Glass, a billionaire who owns an apartment building called the Glass Palace and has a love of all things unique. He hires George as a window washer. Things go well until George sees some shadows in one room that look like jungle animals and decides to paint them. As a result, this causes Mr. Glass to get angry and orders 2 painters to chase George but is rescued by The Man With The Yellow Hat. Although Mr. Glass appreciates the room with the jungle animals and decides to rent it out.

The doorman has to go away for an errand and leaves Hundley in charge. But soon George arrives and puts on the Doorman's uniform. This makes a deliveryman sign off a bunch of packages to him thinking he is the doorman. George opens all of the packages, which contain autographed balls, thinking they are all from him. But when the person who was supposed to receive them sees them, George realizes his mistake. He and Hundley must then work together to re-package them and stack them up.

It's Professor Wiseman's birthday and The Man with the Yellow Hat has bought her a present which George is determined to open. The Man decides to take George's mind off of the present by having him unwrap some oranges for a salad. But soon George wants to know all about different kind of wrapping which leads him down to the department store.

After watching a live video of the new panda on the zoo website, George rushes to the zoo to see it, but gets accidentally locked inside. George tries to find the exit, but mistakenly opens the wrong doors and finds himself surrounded by giraffes, meerkats and penguins. George must put the animals back in their homes.

After a rainy country day, George finds a flock of ducks that have taken refuge in a puddle and spends the day playing with them. The next day George sees that the puddle has shrunk and the ducks are flying off one by one in search of more water. He is determined to do anything to get them to stay around. Then he sees his pool, filled with water and empties it out to get it to the top of the hill where the ducks are. But afterward, he must find a way to re-fill it.

There is a big construction project going on on George's street and George is curious as to what is going on. He comes upon a very active and noisy place and sees everything that is going on. When he returns the next day to find the site abandoned, he winds up going on a quest with Gnocchi and Compass to retrieve a loose $10 bill. Along the way, he needs to use several pieces of equipment, such as jackhammers, excavators, and cement mixers, to get it out of a few tight places.