Frodo, Sam, Merry, and Pippin cross out of the High Hay on their ponies and traverse the Old Forest. Merry tells his companions stories about the haunted forest and the trees’ ability to move and trap strangers who trespass. Hobbits long ago cut down the edge of the forest to maintain the Hedge, and ever since, the trees have become “very unfriendly” (108).

Merry guides the group but is unable to find the path to lead them to the other side and onto the East Road. The stifling air and shifting trees disorient the hobbits, and they succumb to a heavy drowsiness. Everyone but Sam succumbs to this sleeping spell, and he wakes Frodo as he is being dragged into the river by tree roots. As Old Man Willow—an evil spirit in the form of an old willow tree—swallows Pippin whole and half-engulfs Merry, Sam and Frodo light a fire on the other side of the tree but are unsuccessful at rescuing them.

Suddenly, they hear someone “singing nonsense” (116), and there appears a curious spirit dressed in blue with yellow boots and a blue feather in his hat. It is Tom Bombadil, larger than a hobbit but smaller than a man, and when he sings a reprimanding song to Old Man Willow, the tree spits out the hobbits.