The film is actually composed of material from three previously released animated shorts:
- Winnie the Pooh and the Honey Tree (1966)
- Winnie the Pooh and the Blustery Day (1968)
- Winnie the Pooh and Tigger Too! (1974)
The film and its characters have spawned an industry of sequels, television programs, clothing, books, and toys.
The film also inspired an attraction of the same name at both Disneyland and Walt Disney World. A much more elaborate attraction, also based on the film, opened in Tokyo Disneyland as "Pooh's Hunny Hunt".
The film's content comes largely from the three previously released animated featurettes Disney produced based upon the Winnie-the-Pooh books by A. A. Milne: Winnie the Pooh and the Honey Tree (1966), Winnie the Pooh and the Blustery Day (1968), and Winnie the Pooh and Tigger Too! (1974). Extra material used to link the three featurettes together was added to allow the stories to flow into each other.
A fourth, shorter featurette was added to bring the film to a close. The sequence was based on the final chapter of The House at Pooh Corner, where Christopher Robin has to leave the Hundred Acre Wood behind as he is starting school. In it, Christopher Robin and Pooh discuss what they liked doing together and the boy asks his bear to promise to remember him and to keep some of the memories of their time together alive. Pooh agrees to do so, and the film closes with The Narrator saying that wherever Christopher Robin goes, Pooh will always be waiting for him whenever he returns.
- "Winnie the Pooh"
- "Up, Down, Touch the Ground"
- "Rumbly in My Tumbly"
- "Little Black Rain Cloud"
- "Mind Over Matter"
- "A Rather Blustery Day"
- "The Wonderful Thing About Tiggers"
- "Heffalumps and Woozles"
- "Rain, Rain, Rain Came Down, Down, Down"
The Many Adventure of Winnie the Pooh the last film in the Disney canon in which Walt Disney had personal involvement, since one of the shorts (Winnie the Pooh and the Honey Tree) was released during his lifetime, and he was involved in the production of Blustery Day. It was always Walt Disney's intention to create a feature film, but he decided to make shorts instead — after production had begun — to familiarize US audiences with the characters. All three shorts as well as future feature films boast classic songs by the Sherman Brothers including "Winnie the Pooh (song)" and "The Wonderful Thing About Tiggers".
For the character Piglet, hand gestures and other movements were used by the animators to create expressiveness, since he (and Pooh) had the appearance of dolls or stuffed animals with relatively simple button eyes. The scene where Rabbit deals with Pooh's being part of the "decor of his home" was not in the original book, but was reportedly contemplated by Disney when he first read the book.
Film critic Leonard Maltin called the original Pooh featurettes "gems"; he also noted that the artwork resembles the book illustrations, and that the particular length of these featurettes meant that the filmmakers didn't have to "compress or protract their script." The film holds a 92% "fresh" rating from critics on Rotten Tomatoes.
Ruth Hill Viguers, however, when writing in A Critical History of Children’s Literature during the 1960s, mentioned Disney’s Winnie the Pooh along with several other Disney adaptations as having “destroyed the integrity of the original books”.
The Many Adventures of Winnie the Pooh was first released on VHS, Betamax, CED videorecord, and laserdisc in the early 1980s. In 1996, it was re-released on VHS as part of the Masterpiece Collection and included video footage of the making which was shown before the movie starts. It was released on DVD for the first time in 2002 as a 25th Anniversary Edition, with digitally restored picture and sound. The individual shorts had also been released on their own on VHS in the 1990s.
The 25th anniversary edition DVD includes, among other bonus features, "The Many Adventures of Winnie the Pooh: The Story Behind the Masterpiece", which documents the history of the books and their initial film adaptations. It also features interviews with animators Ollie Johnston, Frank Thomas, and Burny Mattinson, as well as the Sherman Brothers, Paul Winchell, and others. Digital Media FX reviewer Shannon Muir stated that the audio and video quality of the film on this DVD was very high.
The "Friendship Edition" DVD was re-released on June 19, 2007. All of the special features from the previous "25th Anniversary Edition" DVD were recycled; the only new addition being an episode of Playhouse Disney's computer-animated series My Friends Tigger & Pooh. The DVD re-release coincides with the 30th anniversary of the release of the film.  The Blu-ray version was released on August 27, 2013. Winnie the Pooh Storybook Classics was released on VHS worldwide in 1994. The featurettes include, Winnie the Pooh and the Honey Tree (February 4, 1966), Winnie the Pooh and the Blustery Day (December 20, 1968), Winnie the Pooh and Tigger Too! (December 20, 1974) and Winnie the Pooh and a Day for Eeyore (March 11, 1983). This VHS was last released in 2000.
Elements of the three featurettes along with the Winnie the Pooh and a Day for Eeyore featurette and The Tigger Movie were incorporated into the video game Winnie the Pooh: Adventures in the Hundred Acre Wood as a part of the gameplay for the video game.