Answer:
There are two meanings to me. With one I may need to be broken, with the other I hold on. My favorite characteristic is my charming dimple.
What flies around all day but never goes anywhere?
I can run but not walk. Wherever I go, thought follows close behind.
I hide but my head is outside.
Brown I am and much admired; many horses have I tried; tire a horse and worry a man; tell me this riddle if you can.
I can only be played on a windy day