Q: "A little boy who is walking in the wilderness by himself." Does this mean that "a child is outside"?
A: it is not possible to tell

Q: "People walking around outside in either fall or winter season." Does this mean that "A group of friends build a snowman outside while running around."?
A: no

Q: "A man is playing an instrument, trying to make money with his case open." Does this mean that "The man is playing a guitar."?
A: it is not possible to tell

Q: "A man and a woman run with other runners in a race." Does this mean that "There is a race with more than two people in it"?
A:
yes