you have a few choices -
1 - easiest - just paint it on, and use bump maps to add any extra detail. ( which you can do with sculptris or blender - both of which are free, but take a moment to learn ...sculptris being the easier of the 2 )
2 - intermediate - there's a software on steam called - Race Track Builder - where you make a terrain and conform tracks and roads to it.- you create the whole terrain with track in that software then may have to export that direct x file to blender to convert to obj.
3 - intermediate / advanced - rigging a track - adding bones to a road / track model then shaping it in scene to your terrain. - ironically enough probably the ugliest of these 3 choices because the bones will bend the tracks with slight corners so any curves won't be smooth / round.
☯🐉
"To define Tao is to defile it" - Lao Tzu