Wayward Pines are large pine trees whose branches droop close to the ground while leaving a large hollow interior. They are scattered throughout the New World, particularly in Westland and the Midlands. They are known as a "friend to any traveler" as the inside hollow area is typically used by travelers as a small but cozy shelter for the night or to wait out a rain. Most wayward pines are large enough to almost allow a grown man (such as Richard) to stand inside. The branches are typically bare near the trunk, with needles on the ends, leaving the hollow interior. The tree is fire-resistant as long as one is careful, allowing the a traveler to build a small campfire inside. The smoke from the fire curls up the center, near the trunk. The needles typically grow so thick that even in a good rain it remains dry inside as well as provides concealment for its inhabitants.

Richard introduces both Kahlan and Nicci to wayward pines as a camp site. Rachel when on the run with the Box of Orden is advised by Wizard Giller to travel from wayward pine to wayward pine until winter comes. She had been using a wayward pine near Tamarang when she was sent out of the castle at night by Princess Violet, which she preferred to being locked in the box in Violet's room. Rachel also used the wayward pine as a hiding place for her doll Sara and her Fire Stick.