Literary bear and animated film star Winnie the Pooh sets the stage in this educational game from Disney, as he drifts down to the ground via balloon to land outside a Treehouse which becomes the home screen. Gopher provides a mailbox with the player's name on it, and Pooh sets down a honey pot which becomes the options screen. On returning to the Treehouse from elsewhere in the Wood, the personalized mailbox may contain messages from game characters who will read the letter out loud when the mailbox is clicked on.
The player begins here in the Hundred-Acre Wood, and travels along one of three paths to the North Woods, the East Woods, or the West Woods to find a number of reading activities, each one introduced by one of Pooh's friends. Actions are performed by pointing and clicking the mouse; the cursor is a bee that flutters it's wings whenever it is over a clickable spot, and carries an arrow when it's over a path to a new area.
Although a printable "Detective License" certificate is issued on finishing one activity, in a departure from this common convention the game introduces a reward system in which the player is given objects for their Treehouse whenever they successfully complete an activity; items that animate when clicked, such as a xylophone that plays a little tune, a spinning pinwheel, a kite that changes it's pattern. Once the player has received prizes from all nine activities he's given a doorbell that can be programmed by pulling sound tiles into place with the mouse. The game manual contains a Parent's Guide showing which level of activity earns which reward - parents can tell what skill level their child has reached in each area by viewing the contents of their Treehouse: if the player's Treehouse contains an area rug, for instance, the guide shows he has reached level two in the Pooh's Honey Pots (Alphabet Sequencing) activity.
- Eeyore's Tattered Books: match the torn pictures to the words on the pages.
- Let's Pretend: Roo is imagining; pick a character and object and Roo will create a sentence.
- Rabbit's Signs: Rabbit's sign-making machine doesn't work quite right; connect the dots to finish making letters.
- Tigger's Bouncin' Boxes: choose the letter to match the sound Tigger's jack-in-the-boxes make.
- Detective Tigger: drag objects onto a felt board as Tigger describes them, then answer a question about his story.
- Owl's Poetry: pick an object to complete Owl's rhyme.
- Tiggers Don't Climb Trees: find the missing letters to finish the quilt so Tigger can land in it.
- Piglet's Cabinets: letter-matching concentration.
- Pooh's Honey Pots: Pooh's honey pots are lettered; put them in alphabetical order on a shelf.
Some of the early-reading skills covered are simple spelling, letter formation, sentence creation, rhyming, memory, alphabet order, upper and lower case letters, and listening.