Winnie-the-Pooh, or Pooh for short, is a soft-voiced, cuddly, loveable and quiet teddy bear and the main protagonist. Despite being naïve and slow-witted, he is a friendly, thoughtful and sometimes insightful character who is always willing to help his friends and try his best. A prime motivation is his love for honey, which quite often leads to trouble.

The only human character in the story books, he has a "cheerful" and compassionate personality and is someone whom Pooh and the others look up to. Despite being a child, he is much wiser and more mature than many of the other characters. Pooh considers both Christopher Robin and Piglet to be his best friends.

Pooh's best friend besides Christopher Robin. In the books, he often takes his lead from Pooh unless overcome by fear which occurs more often than not. But increasingly through the stories he shows himself to be very brave when faced with a crisis and given sufficient encouragement (usually by Pooh). He is fond of "haycorns".

Tigger is Pooh's happy, less-than-responsible and a sometimes troublemaking tiger friend. He bounces around, especially bouncing on others. He is full of energy, outgoing, and likes to have fun and is so overconfident that he thinks that any task is "what tiggers do best".

Rabbit is one of the characters not based on a toy once owned by Christopher Robin Milne. He was said to be based on a real rabbit where they lived. He is friendly, yet capable of being impatient and irritable. He fancies himself the smartest animal in the Hundred Acre Wood, since he is not scatterbrained like Tigger. He insists on doing things his way and is obsessed with rules, planning and order. He often bosses others around, but deep down, he cares a lot about his friends.

Owl is the stuffy and talkative eldest main character who presents himself as a mentor and teacher to the others. He was not based on a stuffed toy, so in the illustrations he looks more like a live animal.

Eeyore is Pooh's ever-glum, pessimistic and sarcastic donkey friend who has trouble keeping his tail attached to his bottom, since the nail keeps falling out. Eeyore has a house made of sticks, which falls apart and has to be rebuilt.

Kanga is a female kangaroo and the doting mother of Roo. The two live in a house near the Sandy Pit in the northwestern part of the forest.Kanga is the only female character to appear in the books and in most Winnie-the-Pooh media.