Why did the woolly bear caterpillar cross the parking lot? November 17, 2016 | Leticia Shaddix Why did the woolly bear caterpillar cross the parking lot? To find a safe spot to spend winter, that’s why. In the spring it will spin a silky cocoon, and two weeks later it will metamorphose into a beautiful tiger moth. Photo: Leticia Shaddix Tagged: animal, caterpillar, insect, moth, nature, wildlife