I think if I were doing a cobblestone road like that, I'd make or find a non-directional cobble texture: round stones spreading in every direction, so that orientation didn't matter. Fill a layer with it, throw on a mask, paint in the wiggly road, then touch up the edges. Come to think of it, though, a sandy verge would be quicker and eliminate the edge problem. I'd have to experiment to come up with the most effective way of doing it, but off the top of my head, I think copy the mask, then a find edges filter, and use that as a mask on a sand texture. Copy the sand layer and mask, blur the new mask, and set the copy's blend mode to Dissolve to get some sand scattered over the stones. Maybe treat the blurred edge with some noise to introduce variation in the width of the scattered sand.

That's just guesswork, though. I'd have to actually fire up Photoshop and try it to know how good a solution it would be.