After a series of misunderstandings, Winnie the Pooh and the gang believe there is a ghost in the Hundred Acre Wood.
The episode begins in a late afternoon, Pooh, Piglet, Rabbit, Tigger and Owl are all playing on a swing hung under a large oak tree in the Hundred Acre Wood. The only ones not there are Eeyore, who is just watching, and Gopher, who pops out in his pajamas complaining about the noise and saying that it is past their bedtime and they should all be sleeping. Upon hearing this, Tigger stops the swing abruptly, causing everyone else to fall, especially Gopher, and enthusiastically states that they must go to bed early in order to wake up early in the next morning and play more. The others follow him, and when Piglet withdraws a little, Tigger tells him that he wouldn't want to stay awake in the night anyway, as there are monsters in the forest, such as 'Bumpitys' and 'Spookables'. This promptly convinces Piglet to run to his house and go to bed.
Deep in the windy night, the forest seems to be full of strange howls and shadows appearing on the windows. Piglet is scared and hides inside a makeshift pillow fort on his bed, covering his ears. Temporarily satisfied that what he can't hear can't hurt him, he looks out of the fort to see an ominous shadow rushing toward him. He quickly ducks back into the fort in a panic, causing a pillow case to fall over his head. Again, he is temporarily reassured by the fact that now he won't be able to see or hear the ghosts. But what if the ghosts see and hear him, he wonders. This mere thought is enough to send Piglet into a panic, and he runs away desperately, still inside his pillow, towards Pooh's house. Unfortunately, the pillowcase prevents him from seeing where he is going, and he accidentally falls into Gopher's hole, waking Gopher, before rushing back out into the night. Moments later, he runs into a sapling which bends back and launches him into the air and onto Pooh's roof, awakening the frightened bear. He tumbles down the roof and onto Pooh's doorstep as Pooh approaches, popgun at the ready. When Pooh opens the door and sees Piglet in the pillow case, he mistakes Piglet for a ghost and runs away to get help. Pooh's screaming, in turn, frightens Piglet, who runs away in the opposite direction.
Meanwhile, Tigger is also hearing lots of strange noises, and, believing them to be 'spookables', decides to go out to investigate. After a while, he locates the source of the noise and declares that he won't let any 'Bumpities' take him by surprise. Just then a large, gray object flies in from out of nowhere, knocking him into a nearby bush. He discovers moments later that the object was Eeyore, who was also the source of the noise. Eeyore admits he is having trouble playing on the swing because he can't stay on without falling. Furthermore, since the others are always playing on the swing during the day, and not giving him a turn, he decided the only time he could practice was at night. Tigger decides to teach Eeyore how to swing.
Later, Pooh, Rabbit, Owl and Gopher have organized a ghost hunting party and are determined to catch the ghost, although they are nervous that the ghost may catch them first. Rabbit, at first takes charge of the group, but relinquishes leadership to Gopher after hearing the ghost wail yet again. As they trek through a hollowed-out tree trunk, they run into Piglet. Thinking him to be the ghost, the group runs away in a panic, with Piglet following, still unable to see where he is going. The group dash up a tree and fall off a limb into a pond, with Piglet following. However, in the fall, Piglet falls out of his pillowcase and lands on Pooh, who asks what he was doing inside of a ghost. Piglet then tells them what happened as they set off to return home. Since Piglet is not the ghost, Rabbit and Gopher are convinced that there must be no ghost after all, but Piglet insists that he had heard one. Suddenly, they all hear Eeyore screaming and are terrified, but soon head back to catch the real ghost.
Meanwhile, Tigger's first attempt to help Eeyore by glueing him to the swing hasn't worked. Tigger realizes the problem is not keeping Eeyore on the swing, but keeping him from crashing to the ground, so he decides to build an improvised glider with a parachute for Eeyore. This actually works: when Eeyore is thrown out of the swing, he flies high into the air before the glider collapses, sending him plummeting to earth. He opens the parachute, but in the dark of the night, his figure is mistaken for a ghost by Pooh and the gang when they arrive. But Tigger, confused by their attitude, explains that there is no ghost, just a donkey swinging in a parachute. Eeyore makes it to the ground, but his parachute gets hung up in the tree and he swings back and forth in the breeze. Tigger then realizes that Eeyore is swinging, and congratulates Eeyore for his success. As the sun shows up, Eeyore's parachute breaks free of the tree and floats away. The gang, seeing that it looks like fun, all join Eeyore for a ride in his parachute. As the group floats off into the distance, Pooh hopes to himself that they won't have to go through this every time Eeyore wants to swing...
Piglet: [wandering through the woods with a pillowcase over his head] I should be brave. At least brave enough to peek out and see something besides my feet. But suppose I peeked out and did see...something besides my feet...POOOH!