Something woeful is full of sadness, like the woeful little boy who can't find the stuffed bunny he needs to fall asleep.
Use the adjective woeful for people or things affected by misery or sorrow. A woeful expression on your face shows you're sad, and a woeful performance in the big kickball game means your team did so badly that you feel miserable about it. Woeful comes from woe, "great sorrow," and its source, the Old English interjection wa. This ancient woeful expression is still used in many languages today.