The film begins with sketches of a young man named Christopher Robin, walking through the Hundred Acre Wood, when he came across a group of unusual adolescent creatures who appeared to be half human. Despite their menacing appearances, the naïve young Christopher ignored the dangers and befriended them all. They introduced themselves as Eeyore, Owl, Rabbit, Piglet, and most importantly, Winnie The Pooh.
The young Christopher began to bring them food, and with each passing day together, their bond grew stronger. The creatures started acting more human-like, even depending on Chris to bring them food. After years of friendship, it was bad for the creatures when Christopher grew up and had to leave his friends to go to college to become a doctor, so he stopped visiting.
Without Christopher around to feed or guide them, and with the arrival of winter, the creatures went into extreme starvation, and in order to survive, the group had to consume one of their own, Eeyore. This traumatized them so much that they developed a hatred for humanity, particularly towards Christopher for abandoning them. They vowed to abandon their humanity, return to their feral instincts, and be permanently silent.
We move to five years later; Christopher, returns to the Hundred Acre Wood to reunite with his old friends. He’s accompanied by his fiancée, Mary, and while leading Mary into the forest, Christopher asks her whether she believes in the stories of his talking animal friends. Mary casts him a sympathetic look and admits that she doesn't quite believe his tales, and she labels his animal friends as a work of imagination.
Chris and Mary come across the creature’s place, and finds the place in a desolate state. A very frightened Mary tells Chris that they should leave, but Chris assures her that his friends aren't a threat. As they walk around, Mary sees a skull, while Chris pays no attention to Eeyore's grave.
Together, the two walk up to Chris's old house with the creatures, and make their way inside. Mary spots a ruined drawing of Chris, which makes Chris doubt the childhood friends he once had. Suddenly, a voice alerts them.
The two quickly hide until the night creeps in. Mary and Chris find the creature snoring on the bed, so the two use this opportunity and bolt straight for the door. Unfortunately, Piglet makes a surprise entrance by wrapping a metallic chain around Mary's neck.
Seeing his future wife dead, Chris runs into hiding. Chris suddenly sees Pooh approaching him, and so he tries to remind Pooh of their childhood days together. Soon, Piglet appears from the other side, trapping Chris between him and Pooh.
Now Chris knows that his friends aren't the same as they used to be, and like many others, he never appeared from the woods again. News of mysterious disappearances in the forest circulates around like wildfire, and reporters warn people to stay as far away as possible from 100 Acre Woods. Later in the movie, we are introduced to a new character, Maria, who is advised by her therapist to disconnect from the busy world around her.
After taking the expert's advice into consideration, Maria and her friends decide to go on a retreat in the woods. But little do they know, the cabin they choose for a retreat is located in a horrible place to stay, the Hundred Acre Wood. The group of college students is amazed when they arrive at the grand cottage, especially since it has a pool.
Upon entering the villa, Jessica asks her friends to hand their phones to her, as using mobile phones will ruin the purpose of the retreat. The girls then discuss how one of their friends, Tina, never shows up on time or ditches the plan last minute. Meanwhile, Tina stops the car in front of the 100 Acre Woods sign, and rings her friends for directions.
When she gets no response from them, Tina steps into the woods. And then all of a sudden, Winnie The Pooh emerges, causing Tina to frantically run towards an abandoned garage. When the coast is clear, Tina comes out of her hiding place.
But when she turns around, she screams in horror as the murderous bear grabs her, and bashes her head multiple times against the wood chipper. Pooh kills Tina by mutilating her body and mincing her in the wood chipper. Back at the villa; after settling in, Maria opens up to her friends about her encounter with a perverted stalker, and how the event scarred her for life.
Her friends supportively smile at her when Maria reveals that she finds herself feeling a lot better. Meanwhile at Pooh's lair, we find Christopher tied to a ceiling, reminding Pooh of the beautiful childhood days. For a moment, Pooh stops and recalls how young Christopher called him best friend, and promised to never leave him.
Sadness washes over him, which quickly turns into anger. Pooh grabs a lash and whips Christopher's back for his betrayal. To hurt him further, Pooh places Mary's skull in front of Christopher, causing him to wail out in deep anguish.
Meanwhile, Lara, who couldn't stand to be without her phone, stealthily takes it back. Later that evening, the psycho pooh is walking in the middle of the woods when he hears the sound of loud music coming from the girls’ cabin. At the same time, Lara enjoys herself in a Jacuzzi tub, while taking selfies for the simps on her Instagram.
After taking multiple pictures of herself, she swipes through them, when suddenly her attention shifts towards a figure standing in the background. She then gets out of the tub to look for the pervert, but finds nothing. Thinking it’s just a prank from her friends, she mindlessly gets back in the Jacuzzi.
While continuing to enjoy herself in the tub, Lara doesn’t realize that Pooh and Piglet are silently intruding. When Lara opens her eyes, she finds herself tied up with Piglet standing next to her, and Pooh revving the car's engine. She begs desperately for life, only for Piglet to give Pooh the green light to crush her head.
Alice and Zoe rush to check up on their friend upon hearing Lara's scream, while Maria and Jessica run outside to find the car door wide open, and the girls come across Lara's crushed head. Frightened out of their wits, the girls gather around, and find a crimson message on their glass doors. Just then, the sound of glass shattering in the distance alerts the girls of an intruder's presence.
Slowly, they check the source of noise, and here the frightened girls find Pooh outside clutching a huge knife. Pooh encircles the cottage, and once he cuts off the power, Zoe and Alice decide to go in the kitchen to arm themselves up, while Maria believes that the intruder is her stalker. Zoe and Alice then return and assure her that the intruder is not her stalker.
It is here where Maria remembers that she’s brought a gun, but while Maria and Jessica go to retrieve it, the four of them accidentally split into pairs. On the other hand, Zoe and Alice have made it to the pool inside the house to shut the back door. But as Zoe tells Alice to run if something were to happen.
In a split second, Piglet appears, and after rendering Alice unconscious, the piglet makes his way to hit Alice with his hammer, but Zoe manages to shift Piglet’s attention to her. He jumps in the water, slinging his hammer to attack Zoe. Alice regains consciousness only to see Piglet killing her friend, and the trauma causes her to faint again.
Soon, Jessica and Maria discover the horrible sight of Zoe's dead body floating in the pool, and watch in horror as they see Piglet and Pooh carrying Alice. Jessica and Maria then decide to follow the blood-hungry creatures to find out where they're taking Alice. Afterwards, we find Alice tied up with a rope at the devils' lair, while Winnie the Psycho Pooh is nibbling on fresh honey from the pot.
When Winnie sees that Alice is awake again, he walks up to her and does this. Later when Jessica and Maria find the coast to be clear, they immediately rush to help Alice out of her bounds. Maria and the girls are making their way out when all of a sudden, they hear a loud yell, and so, the clever Maria tells Jessica and Alice that they shouldn't leave a person behind.
Inside the dilapidated cottage, they see Christopher hanging from the hook. Maria takes careful steps towards his unconscious body, just as Chris instantly rouses up and begs Maria for help, so Maria and the girls immediately begin untying the rope. Once he is free, they suddenly hear a woman's cry for help, so Chris pushes the girls to go and help the woman.
The girls check the source of the agonizing screams, and find a deeply injured woman, tied down with ropes. When Jessica asks the lady about her abusers, the woman replies that it was Pooh and Piglet. She tells them that the pig and the bear can talk and speak in broken English, but they prefer to do their work in silence.
After helping the woman out of the chains, the girls help her escape. But as they walk outside, the woman comes across a mirrored structure, and she screams in horror upon looking at her heavily scarred face. The girls try to stop her from screaming, and then the woman takes the gun from Maria, and to make the story longer, she decides to take revenge by killing the monsters who did this to her.
Jessica, Maria, and Alice decide to hide out of fear for their lives. Finally, Piglet the monster shows up, and accepts the 1-on-1 challenge with no rules. The woman again points her gun and tells him that he turned her into a monster, and for that he will pay.
Unfortunately, as she tries to shoot, the gun is empty, so the woman backs away only for her to bump into Pooh. After dropping the woman on the floor, Pooh pours honey on her face. Then, Piglet sits down to devour her face.
The girls then decide to run off, but Alice notices a hammer, and seizes her chance to attack Piglet. After losing Alice, Maria and Jessica run into the forest with Pooh chasing them. Meanwhile, we see Piglet having been captured by Alice.
She wakes the monster up by slapping him, and tells him that she will make sure he pays for his crimes. Unfortunately, after hammering down Piglet, Alice gets attacked by Pooh, and he kills her with his machete. The bear then continues his chase for more blood.
After a while of running, Maria and Jessica find a car driving towards them. A group of hillbillies appear out of the car, so the girls disclose everything to them, causing the men to doubt their sobriety. But then, The men watch Pooh with curiosity, and decide to hunt the abomination down.
Jessica and Maria take cover in the car and try to warn the men, but they pay no attention to their warnings. The four men approach Pooh with weapons, and after encircling him, Logan hits him hard in the face. But when they see Pooh remains unchanged, Logan signals his boys to launch a combined attack.
To their horror, Pooh still remains strong. Having had enough, it’s now his turn to wipe them out. Seeing Pooh advances towards the car, Maria starts the car, and hits him.
After hitting her head on the steering wheel, Maria watches helplessly as Pooh drags Jessica out of the car. Seconds later, he shows her Jessica's decapitated head. Panicked, Maria tries to keep Pooh away from her, but at the end, he overpowers her.
But just as Pooh is about to kill her with his knife, Luckily, Christopher comes from behind and rams his car into Pooh, saving Maria. When Chris finds Pooh trapped between the cars, he rushes out to help Maria. But as he's helping the girl get back on her feet, Pooh regains consciousness.
He pushes aside the car and picks up his knife. The beast then grabs Maria by the hair, and Chris once again pleads with him to stop his bloody revenge. He further tells Pooh to spare her, promising to permanently stay in the Hundred Acre Wood with him in return.
Hearing this, Pooh slowly lowers his knife at first, but then breaks his silence to tell Christopher; He proceeds to slash Maria's throat. After watching her die in his arms, a traumatized Christopher realizes his former friend is now beyond help, and watches Pooh repeatedly stab her corpse. The film ends as Chris runs off in the woods, raising the specter of future terror from Pooh.
