While searching for honey, Pooh and his friends embark on an adventure to find Eeyore's missing tail and rescue Christopher Robin from an unknown monster called, The Backson. During an ordinary day in Hundred Acre Wood, Winnie the Pooh sets out to find some honey. Misinterpreting a note from Christopher Robin, Owl convinces Tigger, Rabbit, Piglet, Pooh, Kanga, Roo, and Eeyore that their young friend has been captured by a creature named "Backsoon", and they set out to save him.

Lewis is a brilliant inventor who meets mysterious stranger named Wilbur Robinson, whisking Lewis away in a time machine and together they team up to track down Bowler Hat Guy in a showdown that ends with an unexpected twist of fate. Lewis an orphan wants to see what his mother looked like. So he invents a machine that looks through your brain so you can see your memories. But this weird kid says he's from the future and warns him about a guy in a bowler hat. The bowler hat guy messes with his invention and it fails. He decides that he's a failure and no one wants him. But the kid that warned him about the guy is here on a mission to find the bowler hat guy that wants to destroy Lewis. To prove he's from the future he takes Lewis to the future. But the time machine breaks and he's stuck in the future until he fixes it. In the meantime he spends quality time with the family. But the bowler hat guy is about to alter time and it's up to Lewis to save the future.