Much of the filming of the Hundred Acre Wood scenes took place at Ashdown Forest, the original inspiration for the setting, as well as Windsor Great Park.
Some elements from the A.A. Milne stories appear in this film, which did not appear in the previous Disney adaptations. Such as the fact that Owl and Rabbit are the only animals who are REAL animals, rather than stuffed toys, Piglet's predilection for acorns (or "haycorns," as he calls them), and the use of the word "expedition."
Young Christopher Robin's outfit is based on the one he wore in the original Ernest Shepard illustrations.
The opening segment, in which the animals bid Christopher Robin farewell and he promises not to forget Pooh, is loosely adapted from the very last Pooh story written by A.A. Milne.
Brad Garrett (Eeyore) is probably best known for his role as Robert Barone, Ray's older brother on TV Everybody Loves Raymond (1996). In a meeting with the show's head writer Phil Rosenthal, Rosenthal had compared the character to Eeyore. "I am Eeyore," was Garrett's reply. "Yes, exactly," said Rosenthal. "No," said Garrett. "I mean, I AM Eeyore. I do the voice for Eeyore."
Richard M. Sherman: There is a mid-credits scene with some of the film's supporting cast enjoying the beach. The nearby piano player that performs a song is legendary Disney songwriter Sherman.