The drawing (above) by 2nd grader Annalyse Holbert presents a bird’s-eye view of a wooly bear caterpillar – resting atop a flower, or maybe nibbling a petal, as I’ve sometimes seen one do. Her original drawing, in color, shows the black segments at each end, and a beautiful red-brown band in the center. 
Warm October days, especially sunny ones, keep wooly bears active and spur them to look for sheltered places to hibernate in. That’s often their motive in crossing a driveway or a hazardous rural road.
After finding a protected niche under a rock or leaf litter, a wooly bear will curl into a ball, as it does when handled, and will sleep away the winter – aided by a bio-chemical anti-freeze that keeps its cells from freezing. 
Awakening in April or May, the caterpillar will move to a fresher niche to make a cocoon and transform into a small brown “Isabella Tiger Moth”.
There’s also a long tradition that wooly bears serve as weather prophets – the thicker their black segments, and the thinner their central bands, the more severe a given winter will be. (I’m sure there’s a kernel of truth in this, and would love to track down the story’s beginnings.)
And please note: wooly bears and Isabella moths are benign creatures that share our woods and fields. They’ve no interest in rugs and clothes closets!