In this game, Pooh travels through the Hundred Acre Wood, in which he encounters some of his friends, of which leads to playing games and dealing with the Pooh featurettes. Once the player wins each game (in which there are two ways they can win), it becomes a storybook in which the player can view later on. Once each player collects the eight storybooks (two from each of the films), the player experiences another story leading to the end of the game.
- Winnie the Pooh and the Honey Tree (when encountering Rabbit)
- Winnie the Pooh and the Blustery Day (when encountering Piglet)
- Winnie the Pooh and Tigger Too! (when encountering Tigger)
- Winnie the Pooh and a Day for Eeyore (when encountering Eeyore)
- The Tigger Movie (at the end when encountering Christopher Robin and having collected all 8 storybooks)
The Honey Tree
There are two games that the player must get through:
- The first one is Pooh racing Rabbit.
- The second is Rabbit trying to reach Christopher Robin, Piglet, and Eeyore in order to get Pooh unstuck in 18 turns. If won, everyone rescues Pooh. If failed, Pooh becomes unstuck and frees himself.
The Blustery Day
- Pooh must try and rescue Piglet before he falls off of the waterfall. In order to save Piglet, Pooh must reach the same step as Piglet before he falls. If succeeded, everyone celebrates Piglet's rescue. If failed, Christopher Robin rescues Pooh and Piglet from the river.
A Day for Eeyore
- The player must get Eeyore's gifts to his house intact in 8 turns. If the player succeeds, Eeyore gets his gifts (which is honey from Pooh and a balloon from Piglet) intact. However if the player fails, then Eeyore still gets the gifts and is still satisfied but he will get an empty honey pot and a broken balloon.
There are two games (in which the player must play the second game if the player wins the first one) to get through:
- The first is Pooh trying to not get caught by Tigger and must avoid Tigger for ten turns. If Pooh does avoid Tigger, then the story goes on and leading to the second game. If Pooh is caught by Tigger, then the story ends with Tigger finding Pooh, Rabbit, and Piglet and meaning that the trio were unsuccessful at hiding from Tigger.
- The second game (in which you can only access if you win the first game) is Tigger trying to find Rabbit as this game has unlimited turns and ends with the story being with Tigger finding Rabbit and that Pooh and Piglet were already home.
The Tigger Movie
- This section only explains the near end to end of the film in which Tigger tries to find his family and an avalanche happens leading to Tigger's friends to try and rescue him and how Tigger learns his friends are his family. After the story it leads to the end credits.
After Creating a Storybook...
- The player may look at any of their adventures in story form when back in Pooh's house.
There are a few mini games located in Pooh's house and also in a few spots in the Hundred Acre Wood. The mini games include:
- Exercising - The player mush follow the arrows in order to win the game. Pooh moves with the directions of the arrows and the point of the game is to match the arrows with Pooh's movements. The game is hosted by Kanga.
- Acorn Collecting - The player must collect a certain amount of acorns in a certain amount of time. The player as Pooh collects the acorns in his honey pot in which Pooh must dispose of the acorns in baskets on the far right and left of the screen. Pooh can only hold up to five acorns in his honey pot at a time. The game is hosted by Piglet.
- Fishing - The player must catch 25 fish before it gets dark and the game ends. The player as Pooh moves back and fourth catching the fish that pop up from the river. If Pooh catches a turtle, he can't move for a certain time. The game is hosted by Tigger.
- Balloon - The player must ride a balloon up the honey tree to the beehive. Pooh is disguised as a "little black rain cloud" and gets a balloon so he can float up the tree. The player as Pooh moves in any direction, avoiding the bees that randomly appear and fly downwards in lines. If the player gets to the top of the tree, Pooh will reach the beehive and the player wins. If a bee touches Pooh's balloon, it pops and the player loses. The game is hosted by Christopher Robin.
- Racing #1 - You go through a board similar to Racing Game #2 but you may land on any of three spots marked with a sun, moon or star, and that reveals a spot in which you can get access to get cards. Moon and sun steps take you to one of Pooh's friends while star steps take you to a mini-game. The game is hosted by Owl.
- Racing #2 - The player (who can be rather Pooh, Piglet, Eeyore, Tigger, Rabbit, or Roo) goes against another player (which is one of the characters that the player may choose but is played by the computer) in which you must get to the destination before your opponent.
Racing Information for Racing Game
- The steps are determined by a dice, and a puddle counts as two steps.
- The player can move the determined number of spaces either forward or backward.
- If the player or their opponent lands on a step with food the character likes, the player loses three turns in order to eat the food, and there are two steps that have the food.
- There are also launchers that can move a player: the first one moves them forward but the second moves them back.
- The player must land on the finishing platform in the exact steps as the dice.
- The prize is a piece of furniture to help decorate Pooh's home.
- Eligible cards may also be used to help you in the game.
- This game is the only one that is automatically there, while the other mini games the player must win before they can have them in Pooh's house.
The player may also be able to manage Rabbit's garden. In Rabbit's garden, the player gets to plant, water, and harvest carrots. The way the player can do these is by obtaining cards that can do these tasks. Without the cards, the player cannot complete the tasks. If any carrots wilt, there is no penalty. If the player successfully harvests a carrot, they gain a card.
There are cards that can benefit the player rather in the games or in Rabbit's garden. The cards may be obtained in various spots from various characters, such as Owl, Rabbit, Gopher, Piglet, and Tigger. Sometimes, however the character may not have a card to give Pooh. The player can only hold a certain amount of cards, and if they gain a card when their collection is full, then they must discard a card in order to obtain the card the player will receive.
- Sun - Removes all puddles from the game board.
- Rain - It rains, making a few puddles appear on the game board.
- Seed - Plants a carrot in Rabbit's garden.
- Water can - Waters a carrot in Rabbit's garden.
- Bridge - Makes a bridge on the wood map to cross a river.
- If the player goes to Christopher Robin without having all eight books, Christopher Robin tells the player that there is more to discover as it leads to a scene with Pooh walking with Christopher Robin and Piglet as they go on another adventure in which it leads to the player back in Pooh's house.
- The Honey Tree adventure is the only scenario where the player can win one part and fail the other; if this occurs, they will not obtain the storybook of the adventure.