I'm not sure of which you are suggesting, Vincent.
He drove up a winding path. Okay. Suggests he's going up hill.
He drove on a winding path. Okay.
I agree with Mike, by the way, that if you are driving, a road is better than a path.
He drove up his car on a winding path. -- no.
He drove his car up to a winding path -- this sounds like he drove up some hill, t