The Pitfall is a small area that can be found in the Nightmare. It appears to be somewhere in the empty, abyssal darknesses and emptinesses of the Nightmare, with each area of the Pitfall being split up into small fragments that can only be accessed by the pulsing orbs of nightmare (known as Pitfall Orbs) that can spawn anywhere in the Nightmare, or from the trapdoor found in the attic where No-Legs can be found at, in the Inside.
There are three different environments that the players may be taken to, based on the object they had interacted with (the trapdoor or the orb):
Interacting with the orbs (by being dragged forcefully by the orb) will take the players to a long series of a 'wormhole' passage to someplace in the Nightmare's abysses, specifically to the Pitfall's battle area. These 'battle areas' will have one creature of the Nightmare to fight against the players on a platform surrounded by two large spheres, a black sphere, and a white sphere. The platforms are made of cobblestone and are divided by a harmless purple gas. The black sphere and white sphere possibly reference the Yin-yang of Eastern Asia culture, with the players on the side with the black sphere and the monsters on the side with the white sphere. After the players have defeated the monster that was selected by the Nightmare to fight against the players, they may interact with the orb in the center to redirect the players back to their original position in the Nightmare.
If the orb takes the players to a scenario known as the Power Lamp Surgery. Players will have to play the role of Mickey, a 'medical expert' skilled in the surgery of lamps, how the process works, who knows for sure? The objective of Mickey (the players) is to retrieve the correct lamp out of the many fake lamps provided in the room. Interacting with fake lamps causes them explode, taking away large portions of the player's health points, which can easily devastate poorly-equipped players. After the players have acquired the correct lamp, they may interact with a toaster to return to 'safety'.
Interacting with the trapdoor above the Blue Door's exit in the Inside's attic will take the players to a 'dormant' area of the Pitfall, where a floating carpet-like platform ponders about in the empty abysses of the Nightmare. Small furniture can be seen on the platform, similar to the ones seen in the Inside. Players may or may not encounter enemies in the Nightmare, but if they do, they may either encounter the Red Wolf or The Chewed. If the players had passed the smoke particles and interact with the orb, the players will be taken to the first-riddle room, closest to the Green Door. This acts as a 'shortcut' route for players that do not want to spend time counting accurately in order to get to The Plant Room.
- The Pitfall is similar to that of the Rabbit Hole, both places being in some sort of dimension where the skybox is completely black.